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Showing metabocard for p-Aminobenzoic acid (HMDB0001392)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:40 UTC
HMDB IDHMDB0001392
Secondary Accession Numbers
  • HMDB01392
Metabolite Identification
Common Namep-Aminobenzoic acid
Descriptionp-Aminobenzoic acid, also known as 4-aminobenzoic acid or PABA, is an organic compound with molecular formula C7H7NO2. PABA is a white crystalline substance that is only slightly soluble in water. It consists of a benzene ring substituted with an amino group and a carboxylic acid. PABA is an essential nutrient for some bacteria and is sometimes called vitamin Bx. However, PABA is not essential for humans and it varies in its activity from other B vitamins. PABA is sometimes marketed as an essential nutrient under the premise that it can stimulate intestinal bacteria. Certain bacteria in the human intestinal tract such as E. coli generate PABA from chorismate. Humans lack the enzymes to convert PABA into folate, and therefore require folate from dietary sources such as green leafy vegetables. Although some intestinal bacteria can synthesize folate from PABA and some E. coli can synthesize folate this requires six enzymatic activities in folate synthesis which are not all done in the same bacteria. PABA used to be a common sunscreen agent until it was found to also be a sensitizer. The potassium salt of PABA is used therapeutically in fibrotic skin disorders. PABA can also be found in Acetobacter (DOI: 10.3181/00379727-52-14147).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001392 (p-Aminobenzoic acid)

  Mrv1652309042000222D          

 10 10  0  0  0  0            999 V2000
   -0.7698   -0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4843   -0.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1988   -0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1989   -1.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844   -1.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698   -1.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9133   -1.6843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554   -0.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554    0.7907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590   -0.4467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
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3D MOL for HMDB0001392 (p-Aminobenzoic acid)

HMDB0001392
     RDKit          3D
p-Aminobenzoic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
    3.0541    0.0130   -0.0258 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6318    0.0160    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9839    1.1435    0.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3897    1.1829    0.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1084    0.0857    0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5421    0.1409    0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1150    1.1590    0.5886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2913   -0.9366   -0.2432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4666   -1.0468   -0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115   -1.0776   -0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5930   -0.0311   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5334    0.0593    0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706    1.9903    0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8814    2.0912    0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8520   -0.8861   -1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150   -1.9253   -0.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3832   -1.9782   -0.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  8 15  1  0
  9 16  1  0
 10 17  1  0
M  END
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3D SDF for HMDB0001392 (p-Aminobenzoic acid)

  Mrv1652309042000222D          

 10 10  0  0  0  0            999 V2000
   -0.7698   -0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4843   -0.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1988   -0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1989   -1.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844   -1.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698   -1.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9133   -1.6843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554   -0.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554    0.7907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590   -0.4467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001392

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=CC=C(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)

> <INCHI_KEY>
ALYNCZNDIQEVRV-UHFFFAOYSA-N

> <FORMULA>
C7H7NO2

> <MOLECULAR_WEIGHT>
137.136

> <EXACT_MASS>
137.047678473

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.44348919384024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-aminobenzoic acid

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
0.8019027699999998

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.769893805764377

> <JCHEM_PKA_STRONGEST_BASIC>
2.6912772144052126

> <JCHEM_POLAR_SURFACE_AREA>
63.32

> <JCHEM_REFRACTIVITY>
38.0146

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sunbrella

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0001392 (p-Aminobenzoic acid)

HMDB0001392
     RDKit          3D
p-Aminobenzoic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
    3.0541    0.0130   -0.0258 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6318    0.0160    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9839    1.1435    0.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3897    1.1829    0.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1084    0.0857    0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5421    0.1409    0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1150    1.1590    0.5886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2913   -0.9366   -0.2432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4666   -1.0468   -0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115   -1.0776   -0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5930   -0.0311   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5334    0.0593    0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706    1.9903    0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8814    2.0912    0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8520   -0.8861   -1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150   -1.9253   -0.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3832   -1.9782   -0.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  8 15  1  0
  9 16  1  0
 10 17  1  0
M  END
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PDB for HMDB0001392 (p-Aminobenzoic acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.437  -0.834   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.771  -0.064   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.104  -0.834   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.105  -2.374   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.771  -3.144   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.437  -2.374   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -5.438  -3.144   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.103  -0.064   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.103   1.476   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.230  -0.834   0.000  0.00  0.00           O+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4                                                            
CONECT    8    1    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0001392 (p-Aminobenzoic acid)

COMPND    HMDB0001392
HETATM    1  N1  UNL     1       3.054   0.013  -0.026  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.632   0.016   0.012  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.984   1.143   0.478  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.390   1.183   0.529  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.108   0.086   0.109  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.542   0.141   0.168  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.115   1.159   0.589  1.00  0.00           O  
HETATM    8  O2  UNL     1      -3.291  -0.937  -0.243  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.467  -1.047  -0.359  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.912  -1.078  -0.406  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.593  -0.031  -0.911  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.533   0.059   0.921  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.571   1.990   0.801  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.881   2.091   0.904  1.00  0.00           H  
HETATM   15  H5  UNL     1      -3.852  -0.886  -1.090  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.015  -1.925  -0.696  1.00  0.00           H  
HETATM   17  H7  UNL     1       1.383  -1.978  -0.778  1.00  0.00           H  
CONECT    1    2   11   12
CONECT    2    3    3   10
CONECT    3    4   13
CONECT    4    5    5   14
CONECT    5    6    9
CONECT    6    7    7    8
CONECT    8   15
CONECT    9   10   10   16
CONECT   10   17
END
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SMILES for HMDB0001392 (p-Aminobenzoic acid)

NC1=CC=C(C=C1)C(O)=O
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INCHI for HMDB0001392 (p-Aminobenzoic acid)

InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC7H7NO2
Average Molecular Weight137.136
Monoisotopic Molecular Weight137.047678473
IUPAC Name4-aminobenzoic acid
Traditional Namesunbrella
CAS Registry Number150-13-0
SMILES
NC1=CC=C(C=C1)C(O)=O
InChI Identifier
InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)
InChI KeyALYNCZNDIQEVRV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic acids
Alternative Parents
Substituents
  • Aminobenzoic acid
  • Benzoic acid
  • Benzoyl
  • Aniline or substituted anilines
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point188.5 °CNot Available
Boiling Point339.00 to 340.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility6.11 mg/mLNot Available
LogP0.83HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available128.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00000311
[M+H]+Not Available131.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00000311
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Epidermis
  • Fibroblasts
  • Intestine
  • Liver
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified15.0 (5.01-32.0) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.11 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.36 (0.15-0.63) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  3. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Associated OMIM IDs
DrugBank IDDB02362
Phenol Explorer Compound IDNot Available
FooDB IDFDB001037
KNApSAcK IDC00001401
Chemspider ID953
KEGG Compound IDC00568
BioCyc IDP-AMINO-BENZOATE
BiGG IDNot Available
Wikipedia Link4-Aminobenzoic_acid
METLIN ID3261
PubChem Compound978
PDB IDNot Available
ChEBI ID30753
Food Biomarker OntologyNot Available
VMH ID4ABZ
MarkerDB IDNot Available
Good Scents IDrw1198771
References
Synthesis ReferenceSato, Ryu; Kimura, Koichi; Takahashi, Akira. Preparation of p-aminobenzoic acid from styrene polymers. Jpn. Kokai Tokkyo Koho (2007), 13pp.
Material Safety Data Sheet (MSDS)Not Available
General References