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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:22:50 UTC

Update Date

2021-09-26 23:12:44 UTC

HMDB ID

HMDB0256796

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Proglumide

Description

Proglumide, also known as (+-)-proglumide or nulsa, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Proglumide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Proglumide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Proglumide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Proglumide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0256796
     RDKit          3D
Proglumide
 50 50  0  0  0  0  0  0  0  0999 V2000
    3.8498   -3.3390    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0114   -2.1669   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9343   -1.1790    0.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1534    0.0312    0.6313 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8921    1.1285    0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0995    1.1689   -1.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792    2.4436   -1.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7704   -0.0678    0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3118   -1.2140    1.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2711    0.9546    0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    1.5286   -0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5202    2.5661   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5486    3.0774   -2.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3673    3.9425   -2.4865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370    2.5946   -3.0029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5800    0.4605    1.2072 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1749   -0.4988    0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5791   -1.0592   -0.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4610   -1.0086    1.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0599   -2.0248    0.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2854   -2.5370    0.6921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9249   -2.0218    1.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3396   -0.9888    2.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1092   -0.5012    2.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -4.0787   -0.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8406   -2.9378    0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3905   -3.7897    1.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083   -2.6191   -0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5094   -1.8631   -1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524   -0.8758    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610   -1.6669    1.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585    1.1431    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110    2.1264    0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891    1.1790   -1.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7951    0.3396   -1.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2488    2.3656   -2.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430    3.3467   -1.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7154    2.5212   -1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0594    1.8055    1.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5396    0.8345   -1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5262    2.2018   -0.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2997    3.3729    0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4884    2.0666   -0.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3338    2.8723   -2.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1801   -1.1171   -1.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6055   -2.4785   -0.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7692   -3.3389    0.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8852   -2.4236    2.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8296   -0.5796    3.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6759    0.3045    2.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 10 16  1  0
 16 17  2  3
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  7 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 15 44  1  0
 18 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
M  END

  Mrv1572004221603222D          

 24 24  0  0  0  0            999 V2000
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  3  1  0  0  0  0
 13  4  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 15  1  4  0  0  0
 19 17  2  0  0  0  0
 20 12  1  0  0  0  0
 20 13  1  0  0  0  0
 20 18  1  0  0  0  0
 21 16  2  0  0  0  0
 22 16  1  0  0  0  0
 23 17  1  0  0  0  0
 24 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256796

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCN(CCC)C(=O)C(CCC(O)=O)N=C(O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H26N2O4/c1-3-12-20(13-4-2)18(24)15(10-11-16(21)22)19-17(23)14-8-6-5-7-9-14/h5-9,15H,3-4,10-13H2,1-2H3,(H,19,23)(H,21,22)

> <INCHI_KEY>
DGMKFQYCZXERLX-UHFFFAOYSA-N

> <FORMULA>
C18H26N2O4

> <MOLECULAR_WEIGHT>
334.416

> <EXACT_MASS>
334.189257325

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.80397905223369

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(dipropylcarbamoyl)-4-{[hydroxy(phenyl)methylidene]amino}butanoic acid

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
2.9598333656666673

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.589267423867572

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.424596941666154

> <JCHEM_PKA_STRONGEST_BASIC>
2.239871109388718

> <JCHEM_POLAR_SURFACE_AREA>
90.20000000000002

> <JCHEM_REFRACTIVITY>
92.08449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
milide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256796
     RDKit          3D
Proglumide
 50 50  0  0  0  0  0  0  0  0999 V2000
    3.8498   -3.3390    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0114   -2.1669   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9343   -1.1790    0.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1534    0.0312    0.6313 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8921    1.1285    0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0995    1.1689   -1.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792    2.4436   -1.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7704   -0.0678    0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3118   -1.2140    1.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2711    0.9546    0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    1.5286   -0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5202    2.5661   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5486    3.0774   -2.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3673    3.9425   -2.4865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370    2.5946   -3.0029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5800    0.4605    1.2072 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1749   -0.4988    0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5791   -1.0592   -0.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4610   -1.0086    1.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0599   -2.0248    0.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2854   -2.5370    0.6921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9249   -2.0218    1.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3396   -0.9888    2.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1092   -0.5012    2.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -4.0787   -0.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8406   -2.9378    0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3905   -3.7897    1.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083   -2.6191   -0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5094   -1.8631   -1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524   -0.8758    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610   -1.6669    1.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585    1.1431    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110    2.1264    0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891    1.1790   -1.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7951    0.3396   -1.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2488    2.3656   -2.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430    3.3467   -1.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7154    2.5212   -1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0594    1.8055    1.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5396    0.8345   -1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5262    2.2018   -0.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2997    3.3729    0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4884    2.0666   -0.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3338    2.8723   -2.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1801   -1.1171   -1.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6055   -2.4785   -0.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7692   -3.3389    0.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8852   -2.4236    2.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8296   -0.5796    3.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6759    0.3045    2.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 10 16  1  0
 16 17  2  3
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  7 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 15 44  1  0
 18 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  13.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.670   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      12.003   8.470   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      10.669   4.620   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      16.004   4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      14.670   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.336   6.930   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1   12                                                       
CONECT    4    2   13                                                       
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   14                                                       
CONECT    9    7   14                                                       
CONECT   10   11   15                                                       
CONECT   11   10   16                                                       
CONECT   12    3   20                                                       
CONECT   13    4   20                                                       
CONECT   14    8    9   17                                                  
CONECT   15   10   18   19                                                  
CONECT   16   11   21   22                                                  
CONECT   17   14   19   23                                                  
CONECT   18   15   20   24                                                  
CONECT   19   15   17                                                       
CONECT   20   12   13   18                                                  
CONECT   21   16                                                            
CONECT   22   16                                                            
CONECT   23   17                                                            
CONECT   24   18                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0256796
HETATM    1  C1  UNL     1       3.850  -3.339   0.397  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.011  -2.167  -0.149  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.934  -1.179   0.953  1.00  0.00           C  
HETATM    4  N1  UNL     1       2.153   0.031   0.631  1.00  0.00           N  
HETATM    5  C4  UNL     1       2.892   1.128   0.118  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.099   1.169  -1.371  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.879   2.444  -1.754  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.770  -0.068   0.889  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.312  -1.214   1.332  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.271   0.955   0.737  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.377   1.529  -0.628  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.520   2.566  -0.704  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.549   3.077  -2.085  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.367   3.942  -2.487  1.00  0.00           O  
HETATM   15  O3  UNL     1      -0.637   2.595  -3.003  1.00  0.00           O  
HETATM   16  N2  UNL     1      -1.580   0.460   1.207  1.00  0.00           N  
HETATM   17  C12 UNL     1      -2.175  -0.499   0.572  1.00  0.00           C  
HETATM   18  O4  UNL     1      -1.579  -1.059  -0.549  1.00  0.00           O  
HETATM   19  C13 UNL     1      -3.461  -1.009   1.006  1.00  0.00           C  
HETATM   20  C14 UNL     1      -4.060  -2.025   0.309  1.00  0.00           C  
HETATM   21  C15 UNL     1      -5.285  -2.537   0.692  1.00  0.00           C  
HETATM   22  C16 UNL     1      -5.925  -2.022   1.797  1.00  0.00           C  
HETATM   23  C17 UNL     1      -5.340  -0.989   2.524  1.00  0.00           C  
HETATM   24  C18 UNL     1      -4.109  -0.501   2.109  1.00  0.00           C  
HETATM   25  H1  UNL     1       3.982  -4.079  -0.423  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.841  -2.938   0.705  1.00  0.00           H  
HETATM   27  H3  UNL     1       3.390  -3.790   1.276  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.008  -2.619  -0.337  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.509  -1.863  -1.061  1.00  0.00           H  
HETATM   30  H6  UNL     1       3.952  -0.876   1.277  1.00  0.00           H  
HETATM   31  H7  UNL     1       2.461  -1.667   1.827  1.00  0.00           H  
HETATM   32  H8  UNL     1       3.958   1.143   0.542  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.511   2.126   0.493  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.189   1.179  -1.982  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.795   0.340  -1.685  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.249   2.366  -2.776  1.00  0.00           H  
HETATM   37  H13 UNL     1       3.243   3.347  -1.599  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.715   2.521  -1.030  1.00  0.00           H  
HETATM   39  H15 UNL     1      -0.059   1.805   1.434  1.00  0.00           H  
HETATM   40  H16 UNL     1      -0.540   0.834  -1.441  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.526   2.202  -0.754  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.300   3.373   0.026  1.00  0.00           H  
HETATM   43  H19 UNL     1      -2.488   2.067  -0.512  1.00  0.00           H  
HETATM   44  H20 UNL     1       0.334   2.872  -2.890  1.00  0.00           H  
HETATM   45  H21 UNL     1      -2.180  -1.117  -1.386  1.00  0.00           H  
HETATM   46  H22 UNL     1      -3.605  -2.479  -0.577  1.00  0.00           H  
HETATM   47  H23 UNL     1      -5.769  -3.339   0.150  1.00  0.00           H  
HETATM   48  H24 UNL     1      -6.885  -2.424   2.096  1.00  0.00           H  
HETATM   49  H25 UNL     1      -5.830  -0.580   3.387  1.00  0.00           H  
HETATM   50  H26 UNL     1      -3.676   0.304   2.695  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5    8
CONECT    5    6   32   33
CONECT    6    7   34   35
CONECT    7   36   37   38
CONECT    8    9    9   10
CONECT   10   11   16   39
CONECT   11   12   40   41
CONECT   12   13   42   43
CONECT   13   14   14   15
CONECT   15   44
CONECT   16   17   17
CONECT   17   18   19
CONECT   18   45
CONECT   19   20   20   24
CONECT   20   21   46
CONECT   21   22   22   47
CONECT   22   23   48
CONECT   23   24   24   49
CONECT   24   50
END

HMDB0256796
     RDKit          3D
Proglumide
 50 50  0  0  0  0  0  0  0  0999 V2000
    3.8498   -3.3390    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0114   -2.1669   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9343   -1.1790    0.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1534    0.0312    0.6313 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8921    1.1285    0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0995    1.1689   -1.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792    2.4436   -1.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7704   -0.0678    0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3118   -1.2140    1.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2711    0.9546    0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    1.5286   -0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5202    2.5661   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5486    3.0774   -2.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3673    3.9425   -2.4865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370    2.5946   -3.0029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5800    0.4605    1.2072 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1749   -0.4988    0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5791   -1.0592   -0.5493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4610   -1.0086    1.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0599   -2.0248    0.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2854   -2.5370    0.6921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9249   -2.0218    1.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3396   -0.9888    2.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1092   -0.5012    2.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -4.0787   -0.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8406   -2.9378    0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3905   -3.7897    1.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083   -2.6191   -0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5094   -1.8631   -1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524   -0.8758    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610   -1.6669    1.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585    1.1431    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110    2.1264    0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891    1.1790   -1.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7951    0.3396   -1.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2488    2.3656   -2.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430    3.3467   -1.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7154    2.5212   -1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0594    1.8055    1.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5396    0.8345   -1.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5262    2.2018   -0.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2997    3.3729    0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4884    2.0666   -0.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3338    2.8723   -2.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1801   -1.1171   -1.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6055   -2.4785   -0.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7692   -3.3389    0.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8852   -2.4236    2.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8296   -0.5796    3.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6759    0.3045    2.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 10 16  1  0
 16 17  2  3
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  7 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 15 44  1  0
 18 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-4-Benzamido-N,N-dipropylglutaramic acid	ChEBI
(+-)-Proglumide	ChEBI
(RS)-Proglumide	ChEBI
DL-Proglumide	ChEBI
Proglumida	ChEBI
Proglumidum	ChEBI
Racemic proglumide	ChEBI
Nulsa	Kegg
(+-)-4-Benzamido-N,N-dipropylglutaramate	Generator
4-benzamido-5-(dipropylamino)-5-Oxopentanoate	Generator
Xylamide	MeSH
Milid	MeSH
Proglumide	MeSH
Xilamide	MeSH

Chemical Formula

C₁₈H₂₆N₂O₄

Average Molecular Weight

334.416

Monoisotopic Molecular Weight

334.189257325

IUPAC Name

4-(dipropylcarbamoyl)-4-{[hydroxy(phenyl)methylidene]amino}butanoic acid

Traditional Name

milide

CAS Registry Number

Not Available

SMILES

CCCN(CCC)C(=O)C(CCC(O)=O)N=C(O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H26N2O4/c1-3-12-20(13-4-2)18(24)15(10-11-16(21)22)19-17(23)14-8-6-5-7-9-14/h5-9,15H,3-4,10-13H2,1-2H3,(H,19,23)(H,21,22)

InChI Key

DGMKFQYCZXERLX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
N-acyl-alpha amino acid or derivatives
Hippuric acid or derivatives
Alpha-amino acid amide
Benzamide
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
N-acyl-amine
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

racemate (CHEBI:32058 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0256796)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.1	ALOGPS
logP	2.96	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.42	ChemAxon
pKa (Strongest Basic)	2.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	90.2 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	92.08 m³·mol⁻¹	ChemAxon
Polarizability	36.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	182.367	30932474
DeepCCS	[M-H]-	180.009	30932474
DeepCCS	[M-2H]-	213.344	30932474
DeepCCS	[M+Na]+	188.919	30932474
AllCCS	[M+H]+	182.4	32859911
AllCCS	[M+H-H2O]+	179.7	32859911
AllCCS	[M+NH4]+	184.9	32859911
AllCCS	[M+Na]+	185.6	32859911
AllCCS	[M-H]-	178.5	32859911
AllCCS	[M+Na-2H]-	179.0	32859911
AllCCS	[M+HCOO]-	179.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Proglumide	CCCN(CCC)C(=O)C(CCC(O)=O)N=C(O)C1=CC=CC=C1	3838.6	Standard polar	33892256
Proglumide	CCCN(CCC)C(=O)C(CCC(O)=O)N=C(O)C1=CC=CC=C1	2399.4	Standard non polar	33892256
Proglumide	CCCN(CCC)C(=O)C(CCC(O)=O)N=C(O)C1=CC=CC=C1	2541.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Proglumide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-5391000000-f2cca4be43844953da18	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Proglumide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Proglumide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Proglumide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Proglumide GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Proglumide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Proglumide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Proglumide GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Proglumide LC-ESI-qTof , Positive-QTOF	splash10-0a4i-5921100000-c874128dd39584e6e80b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Proglumide , positive-QTOF	splash10-0a4i-5921100000-c874128dd39584e6e80b	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proglumide 10V, Positive-QTOF	splash10-00kr-1359000000-e461c6506cb3050522f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proglumide 20V, Positive-QTOF	splash10-0a4i-3941000000-9961f623b953ec670485	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proglumide 40V, Positive-QTOF	splash10-0006-9500000000-7cdf6de929d78ec28e88	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proglumide 10V, Negative-QTOF	splash10-001i-0139000000-ba6ab6da2ed84b8a7312	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proglumide 20V, Negative-QTOF	splash10-0ue9-3893000000-5da8eeca7fa234faccfc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Proglumide 40V, Negative-QTOF	splash10-0adl-9730000000-d5405c9f0203b65f1b61	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13431

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4753

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Proglumide

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

32058

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Proglumide (HMDB0256796)

MOL for HMDB0256796 (Proglumide)

3D MOL for HMDB0256796 (Proglumide)

3D SDF for HMDB0256796 (Proglumide)

3D-SDF for HMDB0256796 (Proglumide)

PDB for HMDB0256796 (Proglumide)

3D PDB for HMDB0256796 (Proglumide)

SMILES for HMDB0256796 (Proglumide)

INCHI for HMDB0256796 (Proglumide)

Structure for HMDB0256796 (Proglumide)

3D Structure for HMDB0256796 (Proglumide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra