MiMeDB: Showing metabocard for p-Aminobenzoyl glutamate (MMDBc0030165)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:56:30 UTC

Update Date

2022-08-31 17:40:20 UTC

Metabolite ID

MMDBc0030165

Metabolite Identification

Common Name

p-Aminobenzoyl glutamate

Description

P-aminobenzoyl glutamate (PABA-GLU) is a member of the chemical class known as Hippuric Acid Derivatives. These are compounds containing an hippuric acid or a derivative, with a structure characterized the presence of a benzoyl group linked to the N-terminal of a glycine. PABA-GLU can used by E. coli as a growth substrate and a series of 3 enzymes are used to tranport this peptide into the cell and cleave it into glutamate and p-aminobenzoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05301214522D          

 20 20  0  0  0  0            999 V2000
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  6  5  1  0  0  0  0
  7  1  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
  9 14  1  1  0  0  0
 14 11  1  0  0  0  0
 15 10  2  0  0  0  0
 16 10  1  0  0  0  0
 17 11  2  0  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
  9 20  1  1  0  0  0
M  CHG  2  16  -1  19  -1
M  END
> <DATABASE_ID>
MMDBc0030165

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](CCC([O-])=O)(NC(=O)C1=CC=C(N)C=C1)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2O5/c13-8-3-1-7(2-4-8)11(17)14-9(12(18)19)5-6-10(15)16/h1-4,9H,5-6,13H2,(H,14,17)(H,15,16)(H,18,19)/p-2/t9-/m0/s1

> <INCHI_KEY>
GADGMZDHLQLZRI-VIFPVBQESA-L

> <FORMULA>
C12H12N2O5

> <MOLECULAR_WEIGHT>
264.2341

> <EXACT_MASS>
264.074621504

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
24.870781153952734

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(4-aminophenyl)formamido]pentanedioate

> <ALOGPS_LOGP>
0.12

> <JCHEM_LOGP>
-0.8644325885998023

> <ALOGPS_LOGS>
-1.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.6293966512522773

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7157053525784858

> <JCHEM_PKA_STRONGEST_BASIC>
4.513478622628409

> <JCHEM_POLAR_SURFACE_AREA>
135.38

> <JCHEM_REFRACTIVITY>
87.7766

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
p-aminobenzoyl-glutamate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-MAY-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAY-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   20  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    3    7                                                       
CONECT    2    4    7                                                       
CONECT    3    1    8                                                       
CONECT    4    2    8                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    1    2   11                                                  
CONECT    8    3    4   13                                                  
CONECT    9    5   12   14   20                                             
CONECT   10    6   15   16                                                  
CONECT   11    7   14   17                                                  
CONECT   12    9   18   19                                                  
CONECT   13    8                                                            
CONECT   14    9   11                                                       
CONECT   15   10                                                            
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   12                                                            
CONECT   20    9                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

Synonyms

Value	Source
(2S)-2-[(4-Aminobenzoyl)amino]pentanedioate	ChEBI
4-Aminobenzoyl-glutamate	ChEBI
N-(4-Aminobenzoyl)-L-glutamic acid(2-)	ChEBI
p-Aminobenzoyl-glutamate	ChEBI
Para-aminobenzoyl-glutamate	ChEBI
(2S)-2-[(4-Aminobenzoyl)amino]pentanedioic acid	Generator
4-Aminobenzoyl-glutamic acid	Generator
N-(4-Aminobenzoyl)-L-glutamate(2-)	Generator
p-Aminobenzoyl-glutamic acid	Generator
Para-aminobenzoyl-glutamic acid	Generator
p-Aminobenzoyl glutamic acid	Generator
N-(4-Aminobenzoyl)-L-glutamic acid	Generator

Molecular Formula

C₁₂H₁₂N₂O₅

Average Mass

264.2341

Monoisotopic Mass

264.074621504

IUPAC Name

(2S)-2-[(4-aminophenyl)formamido]pentanedioate

Traditional Name

p-aminobenzoyl-glutamate

CAS Registry Number

Not Available

SMILES

[H][C@@](CCC([O-])=O)(NC(=O)C1=CC=C(N)C=C1)C([O-])=O

InChI Identifier

InChI=1S/C12H14N2O5/c13-8-3-1-7(2-4-8)11(17)14-9(12(18)19)5-6-10(15)16/h1-4,9H,5-6,13H2,(H,14,17)(H,15,16)(H,18,19)/p-2/t9-/m0/s1

InChI Key

GADGMZDHLQLZRI-VIFPVBQESA-L

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
Hippuric acid or derivatives
Hippuric acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Aminobenzamide
Aminobenzoic acid or derivatives
Benzamide
Benzoic acid or derivatives
Benzoyl
Aniline or substituted anilines
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Amino acid
Carboxylic acid
Primary amine
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Amine
Organic oxide
Organooxygen compound
Organopnictogen compound
Organic anion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dicarboxylic acid dianion (CHEBI:60903 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.88 g/L	ALOGPS
logP	0.12	ALOGPS
logP	-0.86	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	4.51	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	135.38 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	87.78 m³·mol⁻¹	ChemAxon
Polarizability	24.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0090000000-c01a5d9988337e7fd6e5	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0090000000-b7b73fd54f03c2f1d248	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9350000000-709cbc119a3154a642e2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0090000000-7c26670e35865ebbab02	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0090000000-b17306e76304664579b1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fai-8590000000-b9b41ca8b80d6bf0773c	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25202539

PDB ID

Not Available

ChEBI ID

60903

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Keseler IM, Collado-Vides J, Santos-Zavaleta A, Peralta-Gil M, Gama-Castro S, Muniz-Rascado L, Bonavides-Martinez C, Paley S, Krummenacker M, Altman T, Kaipa P, Spaulding A, Pacheco J, Latendresse M, Fulcher C, Sarker M, Shearer AG, Mackie A, Paulsen I, Gunsalus RP, Karp PD: EcoCyc: a comprehensive database of Escherichia coli biology. Nucleic Acids Res. 2011 Jan;39(Database issue):D583-90. doi: 10.1093/nar/gkq1143. Epub 2010 Nov 21. [PubMed:21097882 ]

Showing metabocard for p-Aminobenzoyl glutamate (MMDBc0030165)

MOL for #<Metabolite:0x00007fecd0dc69e0>

3D MOL for #<Metabolite:0x00007fecd0dc69e0>

3D SDF for #<Metabolite:0x00007fecd0dc69e0>

3D-SDF for #<Metabolite:0x00007fecd0dc69e0>

PDB for #<Metabolite:0x00007fecd0dc69e0>

3D PDB for #<Metabolite:0x00007fecd0dc69e0>

SMILES for #<Metabolite:0x00007fecd0dc69e0>

INCHI for #<Metabolite:0x00007fecd0dc69e0>

Structure for #<Metabolite:0x00007fecd0dc69e0>

3D Structure for #<Metabolite:0x00007fecd0dc69e0>