Hmdb loader

Showing metabocard for p-Aminobenzoic acid (HMDB0001392)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
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
Data?1676999739
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
Download

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
Download

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
Download

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
Download

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
Download

SMILES for HMDB0001392 (p-Aminobenzoic acid)

NC1=CC=C(C=C1)C(O)=O
Download

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)
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
1-Amino-4-carboxybenzeneChEBI
4-Amino-benzoic acidChEBI
4-AminobenzoesaeureChEBI
4-CarboxyanilineChEBI
4-CarboxyphenylamineChEBI
ABEEChEBI
gamma-Aminobenzoic acidChEBI
p-AminobenzoesaeureChEBI
p-CarboxyanilineChEBI
p-CarboxyphenylamineChEBI
PABAChEBI
Para-aminobenzoic acidChEBI
4-Aminobenzoic acidKegg
p-AminobenzoateKegg
RVPaba lipstickKegg
4-Amino-benzoateGenerator
g-AminobenzoateGenerator
g-Aminobenzoic acidGenerator
gamma-AminobenzoateGenerator
Γ-aminobenzoateGenerator
Γ-aminobenzoic acidGenerator
Para-aminobenzoateGenerator
4-AminobenzoateGenerator
acido P-AminobenzoicoHMDB
Acidum paraminobenzoicumHMDB
ActipolHMDB
AmbenHMDB
AminobenzoateHMDB
Aminobenzoic acidHMDB, MeSH
Aniline-4-carboxylateHMDB
Aniline-4-carboxylic acidHMDB
Anti-chromotrichia factorHMDB
Anticanitic vitaminHMDB
Anticantic vitaminHMDB
Antichromotrichia factorHMDB
Bacterial vitamin H1HMDB
Chromotrichia factorHMDB
HacheminaHMDB, MeSH
Kyselina P-aminobenzoovaHMDB
P-amino-BenzoateHMDB
P-amino-Benzoic acidHMDB
PABHMDB
PabacydHMDB
PabafilmHMDB
PabagelHMDB
PabamineHMDB
PabanolHMDB
PapacidumHMDB
ParaminolHMDB, MeSH
ParanateHMDB
PotabaHMDB, MeSH
RomavitHMDB
RvpabaHMDB
SunbrellaHMDB
Super shade by coppertoneHMDB
Trichochromogenic factorHMDB
Trochromogenic factorHMDB
Vitamin BXHMDB
Vitamin h'HMDB
4 Aminobenzoic acidMeSH, HMDB
4 Aminobenzoic acid, potassium saltMeSH, HMDB
EpitelplastMeSH, HMDB
Jumer brand OF aminobenzoic acidMeSH, HMDB
Medea brand OF aminobenzoic acidMeSH, HMDB
ParaminanMeSH, HMDB
4-Aminobenzoate, potassiumMeSH, HMDB
Epit vitMeSH, HMDB
Llorens brand OF aminobenzoic acidMeSH, HMDB
PabasanMeSH, HMDB
Potassium aminobenzoateMeSH, HMDB
4-Aminobenzoic acid, potassium saltMeSH, HMDB
Aminobenzoate, potassiumMeSH, HMDB
Glenwood brand OF potassium aminobezoateMeSH, HMDB
Llorens brand OF aminobenzoic acid sodium saltMeSH, HMDB
Magnesium para-aminobenzoateMeSH, HMDB
Potassium 4 aminobenzoateMeSH, HMDB
Potassium 4-aminobenzoateMeSH, HMDB
P Aminobenzoic acidMeSH, HMDB
Para aminobenzoic acidMeSH, HMDB
Para-aminobenzoate, magnesiumMeSH, HMDB
p-Aminobenzoic acidChEBI
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
Not AvailableNot Available
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
PropertyValueSource
Water Solubility4.41 g/LALOGPS
logP0.78ALOGPS
logP0.8ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.77ChemAxon
pKa (Strongest Basic)2.69ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.01 m³·mol⁻¹ChemAxon
Polarizability13.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.17431661259
DarkChem[M-H]-124.09131661259
AllCCS[M+H]+129.5532859911
AllCCS[M-H]-125.71932859911
DeepCCS[M+H]+125.12630932474
DeepCCS[M-H]-121.40830932474
DeepCCS[M-2H]-158.74830932474
DeepCCS[M+Na]+133.94830932474
AllCCS[M+H]+129.532859911
AllCCS[M+H-H2O]+124.932859911
AllCCS[M+NH4]+133.932859911
AllCCS[M+Na]+135.132859911
AllCCS[M-H]-125.732859911
AllCCS[M+Na-2H]-127.432859911
AllCCS[M+HCOO]-129.232859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.57 minutes32390414
Predicted by Siyang on May 30, 20229.6823 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.57 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid65.5 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid845.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid327.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid82.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid197.7 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid58.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid247.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid283.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)126.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid705.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid144.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid794.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid215.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid257.3 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate438.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA234.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water187.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
p-Aminobenzoic acidNC1=CC=C(C=C1)C(O)=O3040.1Standard polar33892256
p-Aminobenzoic acidNC1=CC=C(C=C1)C(O)=O1549.1Standard non polar33892256
p-Aminobenzoic acidNC1=CC=C(C=C1)C(O)=O1586.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
p-Aminobenzoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(N)C=C11665.0Semi standard non polar33892256
p-Aminobenzoic acid,1TMS,isomer #2C[Si](C)(C)NC1=CC=C(C(=O)O)C=C11814.5Semi standard non polar33892256
p-Aminobenzoic acid,2TMS,isomer #1C[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C)C=C11818.2Semi standard non polar33892256
p-Aminobenzoic acid,2TMS,isomer #1C[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C)C=C11834.1Standard non polar33892256
p-Aminobenzoic acid,2TMS,isomer #1C[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C)C=C11851.5Standard polar33892256
p-Aminobenzoic acid,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C(C(=O)O)C=C1)[Si](C)(C)C1866.9Semi standard non polar33892256
p-Aminobenzoic acid,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C(C(=O)O)C=C1)[Si](C)(C)C1927.8Standard non polar33892256
p-Aminobenzoic acid,2TMS,isomer #2C[Si](C)(C)N(C1=CC=C(C(=O)O)C=C1)[Si](C)(C)C1971.5Standard polar33892256
p-Aminobenzoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C11793.0Semi standard non polar33892256
p-Aminobenzoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C11891.0Standard non polar33892256
p-Aminobenzoic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C11768.3Standard polar33892256
p-Aminobenzoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N)C=C11894.8Semi standard non polar33892256
p-Aminobenzoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=C(C(=O)O)C=C12098.7Semi standard non polar33892256
p-Aminobenzoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C12339.3Semi standard non polar33892256
p-Aminobenzoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C12264.8Standard non polar33892256
p-Aminobenzoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C12118.8Standard polar33892256
p-Aminobenzoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C(C(=O)O)C=C1)[Si](C)(C)C(C)(C)C2356.9Semi standard non polar33892256
p-Aminobenzoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C(C(=O)O)C=C1)[Si](C)(C)C(C)(C)C2317.7Standard non polar33892256
p-Aminobenzoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=C(C(=O)O)C=C1)[Si](C)(C)C(C)(C)C2122.2Standard polar33892256
p-Aminobenzoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12558.9Semi standard non polar33892256
p-Aminobenzoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12484.2Standard non polar33892256
p-Aminobenzoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C12155.6Standard polar33892256
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 Quantified0.36 (0.15-0.63) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
 details
UrineDetected and Quantified0.11 umol/mmol creatinineAdult (>18 years old)BothNormal 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)Download (PDF)
General References
  1. Derewlany LO, Knie B, Koren G: Arylamine N-acetyltransferase activity of the human placenta. J Pharmacol Exp Ther. 1994 May;269(2):756-60. [PubMed:8182542 ]
  2. Laufer D, Cleghorn G, Forstner G, Ellis L, Koren G, Durie P: The bentiromide test using plasma p-aminobenzoic acid for diagnosing pancreatic insufficiency in young children. The effect of two different doses and a liquid meal. Gastroenterology. 1991 Jul;101(1):207-13. [PubMed:2044909 ]
  3. Nathan D, Sakr A, Lichtin JL, Bronaugh RL: In vitro skin absorption and metabolism of benzoic acid, p-aminobenzoic acid, and benzocaine in the hairless guinea pig. Pharm Res. 1990 Nov;7(11):1147-51. [PubMed:2293213 ]
  4. Lankisch PG, Brauneis J, Otto J, Goke B: Pancreolauryl and NBT-PABA tests. Are serum tests more practicable alternatives to urine tests in the diagnosis of exocrine pancreatic insufficiency? Gastroenterology. 1986 Feb;90(2):350-4. [PubMed:3484456 ]
  5. Szewczuk A, Wellman-Bednawska M: The use of gamma-glutamyl-p-aminobenzoic acid as the substrate for determination of gamma-glutamyltranspeptidase activity in blood serum. Clin Chim Acta. 1978 Mar 1;84(1-2):19-26. [PubMed:25149 ]
  6. Kiss Z, Wolfling J, Csati S, Nagy F, Lonovics J, Schneider G: [The ursodeoxycholic acid-p-aminobenzoic acid test in the diagnosis of small bowel bacterial overgrowth syndrome]. Orv Hetil. 1997 May 18;138(20):1255-8. [PubMed:9244859 ]
  7. Szewczuk A, Wellman-Bednawska M: Acyl derivatives of p-aminobenzoic acid as new substrates for the assay of serum acylase activity. Clin Chim Acta. 1978 Mar 1;84(1-2):27-31. [PubMed:305833 ]
  8. Derewlany LO, Knie B, Koren G: Human placental transfer and metabolism of p-aminobenzoic acid. J Pharmacol Exp Ther. 1994 May;269(2):761-5. [PubMed:8182543 ]
  9. Ito S, Maruta K, Imai Y, Kato T, Ito M, Nakajima S, Fujita K, Kurahashi T: Urinary p-aminobenzoic acid determined in the pancreatic function test by liquid chromatography, with electrochemical detection. Clin Chem. 1982 Feb;28(2):323-6. [PubMed:6976857 ]
  10. Durie PR, Yung-Jato LY, Soldin SJ, Verjee Z, Ellis L: Bentiromide test using liquid-chromatographic measurement of p-aminobenzoic acid and its metabolites for diagnosing pancreatic insufficiency in childhood. J Pediatr. 1992 Sep;121(3):413-6. [PubMed:1517919 ]