ChemFOnt: Showing chemical card for Oleanolic acid 3-acetate (CFc000282439)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:48 UTC

Chemfont ID

CFc000282439

Molecule Identification

Common Name

Oleanolic acid 3-acetate

Definition

Oleanolic acid 3-acetate, also known as 3-O-acetyloleanolic acid, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Oleanolic acid 3-acetate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Oleanolic acid 3-acetate can be found in black-eyed pea and rosemary, which makes oleanolic acid 3-acetate a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-O-Acetyloleanolate	Generator
3-Acetyloleanolic acid	MeSH
Oleanolic acid 3-acetate	MeSH
3-O-Acetyloleanolic acid	ChEMBL
Acetyl oleanolate	Generator
Oleanolate 3-acetate	Generator
Oleanolic acid 3-acetic acid	Generator

Chemical Formula

C₃₂H₅₀O₄

Average Molecular Weight

498.748

Monoisotopic Molecular Weight

498.37091009

IUPAC Name

(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

CAS Registry Number

None

SMILES

[H][C@@]1(CC[C@@]2(C)[C@@]([H])(CC[C@]3(C)[C@]2([H])CC=C2[C@]4([H])CC(C)(C)CC[C@@]4(CC[C@@]32C)C(O)=O)C1(C)C)OC(C)=O

InChI Identifier

InChI=1S/C32H50O4/c1-20(33)36-25-12-13-29(6)23(28(25,4)5)11-14-31(8)24(29)10-9-21-22-19-27(2,3)15-17-32(22,26(34)35)18-16-30(21,31)7/h9,22-25H,10-19H2,1-8H3,(H,34,35)/t22-,23-,24+,25-,29-,30+,31+,32-/m0/s1

InChI Key

RIXNFYQZWDGQAE-DFHVBEEKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302923)

Food

Herb and spice

Herb

Rosemary (FooDB: FOOD00159)

Pulse

Pea

Black-eyed pea (FooDB: FOOD00523)

Process

Not Available

Role

Biological role

Anti-inflammatory (HMDB: HMDB0302923)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00017 g/L	ALOGPS
logP	7.48	ALOGPS
logP	7.04	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	4.74	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	142.78 m³·mol⁻¹	ChemAxon
Polarizability	59.5 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0302923

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006905

KNApSAcK ID

C00033565

Chemspider ID

133265

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

151202

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Oleanolic acid 3-acetate (CFc000282439)

MOL for CFc000282439 (Oleanolic acid 3-acetate)

3D MOL for CFc000282439 (Oleanolic acid 3-acetate)

3D SDF for CFc000282439 (Oleanolic acid 3-acetate)

3D-SDF for CFc000282439 (Oleanolic acid 3-acetate)

PDB for CFc000282439 (Oleanolic acid 3-acetate)

3D PDB for CFc000282439 (Oleanolic acid 3-acetate)

SMILES for CFc000282439 (Oleanolic acid 3-acetate)

INCHI for CFc000282439 (Oleanolic acid 3-acetate)

Structure for CFc000282439 (Oleanolic acid 3-acetate)

3D Structure for CFc000282439 (Oleanolic acid 3-acetate)