Showing Compound Oleanolic acid (FDB013034)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:29 UTC

Update date

2019-11-26 03:07:54 UTC

Primary ID

FDB013034

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Oleanolic acid

Description

Occurs as glycosides in cloves (Syzygium aromaticum), sugar beet (Beta vulgaris), olive leaves, etc. Very widely distributed aglycone Oleanolic acid or oleanic acid is a naturally occurring triterpenoid, widely distributed in food and medicinal plants, related to betulinic acid. It can be found in Phytolacca americana (American pokeweed), and Syzygium spp, garlic, etc. It is relatively non-toxic, antitumor, and hepatoprotective, as well as exhibiting antiviral properties.

CAS Number

508-02-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3beta-Hydroxyolean-12-en-28-Oic acid	ChEBI
Astrantiagenin C	ChEBI
Caryophyllin	ChEBI
Giganteumgenin C	ChEBI
Oleanic acid	ChEBI
Virgaureagenin b	ChEBI
Oleanolate	Kegg
3b-Hydroxyolean-12-en-28-Oate	Generator
3b-Hydroxyolean-12-en-28-Oic acid	Generator
3beta-Hydroxyolean-12-en-28-Oate	Generator
3Β-hydroxyolean-12-en-28-Oate	Generator
3Β-hydroxyolean-12-en-28-Oic acid	Generator
Oleanate	Generator
(3-beta)-3-Hydroxyolean-12-en-28-oate	HMDB
(3-beta)-3-Hydroxyolean-12-en-28-oic acid	HMDB
(3.beta.)-3-beta-hydroxy-olean-12-en-28-oate	HMDB
(3.beta.)-3-beta-hydroxy-olean-12-en-28-oic acid	HMDB
(3.beta.)-3-hydroxy-olean-12-en-28-oate	HMDB
(3.beta.)-3-hydroxy-olean-12-en-28-oic acid	HMDB
(4AS,5S,6as,6BR,8R,8ar,10S,12ar,12BR,14BS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid	HMDB
3-beta-Hydroxyolean-12-en-28-oate	HMDB
3-beta-Hydroxyolean-12-en-28-oic acid	HMDB
3.beta.-hydroxy-olean-12-en-28-oate	HMDB
3.beta.-hydroxy-olean-12-en-28-oic acid	HMDB
3beta-Hydroxy-olean-12-en-28-oate	HMDB
3beta-Hydroxy-olean-12-en-28-oic acid	HMDB
Oleanane triterpenes	MeSH, HMDB
Triterpenes, oleanane	MeSH, HMDB
Oleanol	MeSH, HMDB
Hederins	MeSH, HMDB
(3beta)-3-Hydroxyolean-12-en-28-oic acid	PhytoBank
(3β)-3-Hydroxyolean-12-en-28-oic acid	PhytoBank
(+)-Oleanolic acid	PhytoBank
Gledigenin 1	PhytoBank
Oleonolic acid	PhytoBank
OA	PhytoBank
(3.beta.)-3-beta-hydroxy-olean-12-en-28-Oate	HMDB
(3.beta.)-3-beta-hydroxy-olean-12-en-28-Oic acid	HMDB
(3.beta.)-3-hydroxy-olean-12-en-28-Oate	HMDB
(3.beta.)-3-hydroxy-olean-12-en-28-Oic acid	HMDB
(4AS,5S,6as,6br,8R,8ar,10S,12ar,12br,14bs)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid	HMDB
3.beta.-hydroxy-olean-12-en-28-Oate	HMDB
3.beta.-hydroxy-olean-12-en-28-Oic acid	HMDB
3beta-Hydroxy-olean-12-en-28-Oate	HMDB
3beta-Hydroxy-olean-12-en-28-Oic acid	HMDB
3β-hydroxyolean-12-en-28-Oate	Generator
3β-hydroxyolean-12-en-28-Oic acid	Generator
Olean-12-en-28-oic acid, 3-beta-hydroxy- (8CI)	biospider
Olean-12-en-28-oic acid, 3-hydroxy-, (3-beta)-	biospider
Olean-12-en-28-oic acid, 3-hydroxy-, (3β)-	biospider
Olean-12-en-28-oic acid, 3β-hydroxy-	biospider
Olean-12-en-28-oic acid, 3beta-hydroxy- (8CI)	biospider
Oleanolic acid	db_source
Virgaureagenin B	db_source

Predicted Properties

Not Available

Chemical Formula

C30H48O3

IUPAC name

InChI Identifier

InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1

InChI Key

MIJYXULNPSFWEK-GTOFXWBISA-N

Isomeric SMILES

CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(O)=O

Average Molecular Weight

456.711

Monoisotopic Molecular Weight

456.360345406

Classification

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
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

hydroxy monocarboxylic acid (CHEBI:37659 )
pentacyclic triterpenoid (CHEBI:37659 )
Oleanane triterpenoids (C17148 )
Oleananes (C17148 )
Oleanane triterpenoids (LMPR0106150004 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Cell and elements:

Extracellular

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Olive oil

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 78.90%; H 10.59%; O 10.51%	DFC
Melting Point	Mp 306-308°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]12D +79.5 (CHCl3)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Not Available

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

37659

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB02364

CRC / DFC (Dictionary of Food Compounds) ID

KMF67-H:HNW57-L

EAFUS ID

Not Available

Dr. Duke ID

OLEANOLIC-ACID|BETA-OLEANOLIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00019064

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Oleanolic_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
abortifacient	50691	A chemical substance that interrupts pregnancy after implantation.	DUKE
anti allergic	50857	A drug used to treat allergic reactions.	DUKE
anti arrhythmic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anti atherosclerotic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti carcinomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti cariogenic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti complement			DUKE
anti edemic			DUKE
anti fertility			DUKE
anti gingivitic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti hepatotoxic	62868	Any compound that is able to prevent damage to the liver.	DUKE
anti HIV	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti hyperlipidemic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti ischemic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti leukemic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti leukotriene	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti malarial	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti nephritic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti periodontic			DUKE
anti peroxidant			DUKE
anti prostaglandin-E2	49023	A compound that inhibits the action of prostaglandins.	DUKE
anti plaque			DUKE
anti plasmodial	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti sarcomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti TGF-beta	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
aromatase inhibitor	50790	An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones.	DUKE
beta-blocker			DUKE
beta-glucuronidase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cardioprotective	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
cardiotonic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
cyclooxygenase-2 inhibitor	50629	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.	DUKE
cyclooxygenase inhibitor	35544	A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.	DUKE
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE
elastase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
hypolipemic			DUKE
hypotensive			DUKE
immunomodulator	50846	Biologically active substance whose activity affects or plays a role in the functioning of the immune system.	DUKE
leucocytogenic			DUKE
NF-kappa-B inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
phagocytotic			DUKE
piscicide			DUKE
prostaglandin synthesis inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE
utero tonic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
vasopressor			DUKE