FComEx: Oleanolic acid (PC000818)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:55 UTC

Update date

2017-01-19 02:36:37 UTC

FoodComEx ID

PC000818

FoodDB Record

FDB013034

Chemical Information

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
(+)-Oleanolic acid	manual
(3-beta)-3-Hydroxyolean-12-en-28-oate	biospider
(3-beta)-3-Hydroxyolean-12-en-28-oic acid	biospider
(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	biospider
3-beta-Hydroxyolean-12-en-28-oic acid	biospider
3.beta.-hydroxy-olean-12-en-28-Oate	HMDB
3.beta.-hydroxy-olean-12-en-28-Oic acid	HMDB
3b-Hydroxyolean-12-en-28-Oate	Generator
3b-Hydroxyolean-12-en-28-Oic acid	Generator
3beta-Hydroxy-olean-12-en-28-Oate	HMDB
3beta-Hydroxy-olean-12-en-28-Oic acid	HMDB
3beta-Hydroxyolean-12-en-28-Oate	Generator
3beta-Hydroxyolean-12-en-28-Oic acid	ChEBI
3β-hydroxyolean-12-en-28-Oate	Generator
3β-hydroxyolean-12-en-28-Oic acid	Generator
Astrantiagenin C	db_source
Caryophyllin	db_source
Giganteumgenin C	db_source
Gledigenin 1	db_source
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
Oleanate	Generator
Oleanic acid	db_source
Oleanolic acid	db_source
Virgaureagenin B	db_source

Chemical Formula

C30H48O3

IUPAC name

(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-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

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

Chemical Taxonomy

Description

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

Kingdom