Cannabis Compound Database: Showing Compound Card for p-Aminobenzoic acid (CDB005168)

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Record Information

Version

1.0

Created at

2020-04-17 19:16:10 UTC

Updated at

2020-11-18 16:39:28 UTC

CannabisDB ID

CDB005168

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

p-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. p-Aminobenzoic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.

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

137.14

Monoisotopic Molecular Weight

137.0477

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 )

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

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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	p-Aminobenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00yl-1960000000-b22b04854c131470802a	Spectrum
GC-MS	p-Aminobenzoic acid, 1 TMS, GC-MS Spectrum	splash10-0fkc-2900000000-dec9b6851633ff2c426c	Spectrum
GC-MS	p-Aminobenzoic acid, 2 TMS, GC-MS Spectrum	splash10-00yl-2890000000-b299bfaaed61286c2ff6	Spectrum
GC-MS	p-Aminobenzoic acid, non-derivatized, GC-MS Spectrum	splash10-0079-9600000000-075c262f1e5d23ef097d	Spectrum
GC-MS	p-Aminobenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00yl-1960000000-b22b04854c131470802a	Spectrum
GC-MS	p-Aminobenzoic acid, non-derivatized, GC-MS Spectrum	splash10-0fkc-2900000000-dec9b6851633ff2c426c	Spectrum
GC-MS	p-Aminobenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00yl-2890000000-b299bfaaed61286c2ff6	Spectrum
GC-MS	p-Aminobenzoic acid, non-derivatized, GC-MS Spectrum	splash10-00yl-1960000000-4d7d9e3e3a7a741c72ca	Spectrum
Predicted GC-MS	p-Aminobenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00kr-5900000000-8244277f60fc465369b8	Spectrum
Predicted GC-MS	p-Aminobenzoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006x-4900000000-299c72af4aa4008292bc	Spectrum
Predicted GC-MS	p-Aminobenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	p-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