AFCDB: 4-Aminobenzoic acid (FDB001037)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:48 UTC

Update date

2020-09-17 15:40:49 UTC

Primary ID

FDB001037

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

4-Aminobenzoic acid

Description

p-Aminobenzoic acid, also known as PABA or p-aminobenzoate, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. p-Aminobenzoic acid is a moderately basic compound (based on its pKa). p-Aminobenzoic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, p-Aminobenzoic acid is found, on average, in the highest concentration within pineapples. p-Aminobenzoic acid has also been detected, but not quantified in, milk (cow) and rices. This could make p-aminobenzoic acid a potential biomarker for the consumption of these foods. An aminobenzoic acid in which the amino group is para to the carboxy group.

CAS Number

150-13-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.41 g/L	ALOGPS
logP	0.78	ALOGPS
logP	0.8	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	4.77	ChemAxon
pKa (Strongest Basic)	2.69	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	38.01 m³·mol⁻¹	ChemAxon
Polarizability	13.44 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

Chemical Formula

C7H7NO2

IUPAC name

4-aminobenzoic acid

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

Isomeric SMILES

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

Average Molecular Weight

137.136

Monoisotopic Molecular Weight

137.047678473

Classification

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Aminobenzoic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aminobenzoic acid (CHEBI:30753 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Acetobacter suboxydans

Plant:

Poaceae

Biological location:

Cell and elements:

Cell:

Fibroblast

Organ and components:

Biofluid and excreta:

Tissue and substructures:

Placenta

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 61.31%; H 5.14%; N 10.21%; O 23.33%	DFC
Melting Point	Mp 188-188.5°	DFC
Boiling Point	Not Available
Experimental Water Solubility	6.11 mg/mL at 30 oC	YALKOWSKY,SH & HE,Y (2003)
Experimental logP	0.83	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 4.87 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00dr-8900000000-bface88b2e77a7dce6e1	2015-03-01	View Spectrum
GC-MS	4-Aminobenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00yl-1960000000-b22b04854c131470802a	Spectrum
GC-MS	4-Aminobenzoic acid, 1 TMS, GC-MS Spectrum	splash10-0fkc-2900000000-dec9b6851633ff2c426c	Spectrum
GC-MS	4-Aminobenzoic acid, 2 TMS, GC-MS Spectrum	splash10-00yl-2890000000-b299bfaaed61286c2ff6	Spectrum
GC-MS	4-Aminobenzoic acid, non-derivatized, GC-MS Spectrum	splash10-0079-9600000000-075c262f1e5d23ef097d	Spectrum
GC-MS	4-Aminobenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00yl-1960000000-b22b04854c131470802a	Spectrum
GC-MS	4-Aminobenzoic acid, non-derivatized, GC-MS Spectrum	splash10-0fkc-2900000000-dec9b6851633ff2c426c	Spectrum
GC-MS	4-Aminobenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00yl-2890000000-b299bfaaed61286c2ff6	Spectrum
GC-MS	4-Aminobenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00yl-1960000000-4d7d9e3e3a7a741c72ca	Spectrum
Predicted GC-MS	4-Aminobenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00kr-5900000000-8244277f60fc465369b8	Spectrum
Predicted GC-MS	4-Aminobenzoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006x-4900000000-299c72af4aa4008292bc	Spectrum
Predicted GC-MS	4-Aminobenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Aminobenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00ku-4900000000-ab0d2860a4f23e4fcad4	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00mo-9100000000-667a53f89529678400c7	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-0bbc34587525655f98ef	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0900000000-8f6c193895f5adf391be	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-9200000000-78f63538a3011f036551	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-9000000000-521edb7d484c452d0da3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-7ae0035594587960bab7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-00kf-9000000000-35088605171b150e8b08	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-3900000000-d67f9d252f758529a83c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-1900000000-e4d34d9516fe889137f6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-6900000000-387d1a3c2d588c6f8552	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00r6-9200000000-9ef61d003f891b00406f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9000000000-eaf693e5f0cde39a548e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000i-7900000000-225973eab49386396fa9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-8f6c193895f5adf391be	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9200000000-78f63538a3011f036551	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-521edb7d484c452d0da3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-7ae0035594587960bab7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00kf-9000000000-35088605171b150e8b08	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0900000000-173f144fba431cca9164	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-ab3524c5aadc6fdc28cb	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9200000000-67cea679b40b94c39ac0	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3900000000-682d5d9d22372ece770b	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-9600000000-8d4bba3f647000005bb0	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-5d9b80bb0601c2f238c2	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

30753

Phenol-Explorer ID

Not Available

DrugBank ID

DB02362

HMDB ID

HMDB01392

CRC / DFC (Dictionary of Food Compounds) ID

BQP21-U:BQP21-U

EAFUS ID

164

Dr. Duke ID

P-AMINOBENZOIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00001401

HET ID

PAB

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

p-Aminobenzoic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
anti arthritic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti rickettsial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti thyroid			DUKE
anti tubercular	33282	A substance that kills or slows the growth of bacteria.	DUKE
detoxicant	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
sunscreen	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

4-Aminobenzoic acid (FDB001037)

Structure for FDB001037 (4-Aminobenzoic acid)