Milk Composition Database: Showing metabocard for p-Aminobenzoic acid (BMDB0001392)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:45:19 UTC

Update Date

2020-05-11 20:48:39 UTC

MCDB ID

BMDB0001392

Secondary Accession Numbers

BMDB01392

Metabolite Identification

Common Name

p-Aminobenzoic acid

Description

4-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. 4-Aminobenzoic acid exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. 4-Aminobenzoic acid exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Amino-4-carboxybenzene	ChEBI
4-Amino-benzoic acid	ChEBI
4-Aminobenzoesaeure	ChEBI
4-Carboxyaniline	ChEBI
4-Carboxyphenylamine	ChEBI
ABEE	ChEBI
gamma-Aminobenzoic acid	ChEBI
p-Aminobenzoesaeure	ChEBI
p-Carboxyaniline	ChEBI
p-Carboxyphenylamine	ChEBI
PABA	ChEBI
Para-aminobenzoic acid	ChEBI
4-Aminobenzoic acid	Kegg
p-Aminobenzoate	Kegg
RVPaba lipstick	Kegg
4-Amino-benzoate	Generator
g-Aminobenzoate	Generator
g-Aminobenzoic acid	Generator
gamma-Aminobenzoate	Generator
Γ-aminobenzoate	Generator
Γ-aminobenzoic acid	Generator
Para-aminobenzoate	Generator
4-Aminobenzoate	Generator
acido P-Aminobenzoico	HMDB
Acidum paraminobenzoicum	HMDB
Actipol	HMDB
Amben	HMDB
Aminobenzoate	HMDB
Aminobenzoic acid	HMDB, MeSH
Aniline-4-carboxylate	HMDB
Aniline-4-carboxylic acid	HMDB
Anti-chromotrichia factor	HMDB
Anticanitic vitamin	HMDB
Anticantic vitamin	HMDB
Antichromotrichia factor	HMDB
Bacterial vitamin H1	HMDB
Chromotrichia factor	HMDB
Hachemina	HMDB, MeSH
Kyselina P-aminobenzoova	HMDB
P-amino-Benzoate	HMDB
P-amino-Benzoic acid	HMDB
PAB	HMDB
Pabacyd	HMDB
Pabafilm	HMDB
Pabagel	HMDB
Pabamine	HMDB
Pabanol	HMDB
Papacidum	HMDB
Paraminol	HMDB, MeSH
Paranate	HMDB
Potaba	HMDB, MeSH
Romavit	HMDB
Rvpaba	HMDB
Sunbrella	HMDB
Super shade by coppertone	HMDB
Trichochromogenic factor	HMDB
Trochromogenic factor	HMDB
Vitamin BX	HMDB
Vitamin h'	HMDB
4 Aminobenzoic acid	MeSH, HMDB
4 Aminobenzoic acid, potassium salt	MeSH, HMDB
Epitelplast	MeSH, HMDB
Jumer brand OF aminobenzoic acid	MeSH, HMDB
Medea brand OF aminobenzoic acid	MeSH, HMDB
Paraminan	MeSH, HMDB
4-Aminobenzoate, potassium	MeSH, HMDB
Epit vit	MeSH, HMDB
Llorens brand OF aminobenzoic acid	MeSH, HMDB
Pabasan	MeSH, HMDB
Potassium aminobenzoate	MeSH, HMDB
4-Aminobenzoic acid, potassium salt	MeSH, HMDB
Aminobenzoate, potassium	MeSH, HMDB
Glenwood brand OF potassium aminobezoate	MeSH, HMDB
Llorens brand OF aminobenzoic acid sodium salt	MeSH, HMDB
Magnesium para-aminobenzoate	MeSH, HMDB
Potassium 4 aminobenzoate	MeSH, HMDB
Potassium 4-aminobenzoate	MeSH, HMDB
P Aminobenzoic acid	MeSH, HMDB
Para aminobenzoic acid	MeSH, HMDB
Para-aminobenzoate, magnesium	MeSH, HMDB
p-Aminobenzoic acid	ChEBI

Chemical Formula

C₇H₇NO₂

Average Molecular Weight

137.136

Monoisotopic Molecular Weight

137.047678473

IUPAC Name

4-aminobenzoic acid

Traditional Name

sunbrella

CAS Registry Number

150-13-0

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 Key

ALYNCZNDIQEVRV-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.

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	188.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	6.11 mg/mL	Not Available
LogP	0.83	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
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	1	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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00yl-1960000000-b22b04854c131470802a	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0fkc-2900000000-dec9b6851633ff2c426c	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00yl-2890000000-b299bfaaed61286c2ff6	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0079-9600000000-075c262f1e5d23ef097d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00yl-1960000000-b22b04854c131470802a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fkc-2900000000-dec9b6851633ff2c426c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00yl-2890000000-b299bfaaed61286c2ff6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00yl-1960000000-4d7d9e3e3a7a741c72ca	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kr-5900000000-8244277f60fc465369b8	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006x-4900000000-299c72af4aa4008292bc	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00ku-4900000000-ab0d2860a4f23e4fcad4	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00mo-9100000000-667a53f89529678400c7	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-0bbc34587525655f98ef	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0900000000-8f6c193895f5adf391be	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-9200000000-78f63538a3011f036551	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-9000000000-521edb7d484c452d0da3	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-7ae0035594587960bab7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-00kf-9000000000-35088605171b150e8b08	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-3900000000-d67f9d252f758529a83c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-1900000000-e4d34d9516fe889137f6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-6900000000-387d1a3c2d588c6f8552	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00r6-9200000000-9ef61d003f891b00406f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-9000000000-eaf693e5f0cde39a548e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000i-7900000000-225973eab49386396fa9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-8f6c193895f5adf391be	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9200000000-78f63538a3011f036551	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-521edb7d484c452d0da3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-7ae0035594587960bab7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00kf-9000000000-35088605171b150e8b08	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0900000000-173f144fba431cca9164	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-ab3524c5aadc6fdc28cb	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9200000000-67cea679b40b94c39ac0	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3900000000-682d5d9d22372ece770b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-9600000000-8d4bba3f647000005bb0	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-5d9b80bb0601c2f238c2	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00dr-8900000000-bface88b2e77a7dce6e1	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Not Available	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View 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)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 29291809	details

External Links

HMDB ID

HMDB0001392

DrugBank ID

DB02362

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

4-Aminobenzoic_acid

METLIN ID

3261

PubChem Compound

978

PDB ID

Not Available

ChEBI ID

30753

References

Synthesis Reference

Sato, 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

Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Showing metabocard for p-Aminobenzoic acid (BMDB0001392)

Structure for BMDB0001392 (p-Aminobenzoic acid)