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Substance Name: Oleanolic acid
RN: 508-02-1
UNII: 6SMK8R7TGJ
InChIKey: MIJYXULNPSFWEK-GTOFXWBISA-N

Note

  • A pentacyclic triterpene that occurs widely in many PLANTS as the free acid or the aglycone for many SAPONINS. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin.

Molecular Formula

  • C30-H48-O3

Molecular Weight

  • 456.706
 

Classification Code

  • Drug / Therapeutic Agent
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Names and Synonyms

Name of Substance

  • Oleanolic acid

MeSH Heading

  • Oleanolic acid

Synonyms

  • (3-beta)-3-Hydroxyolean-12-en-28-oic acid
  • 3-beta-Hydroxyolean-12-en-28-oic acid
  • Astrantiagenin C
  • Caryophyllin
  • CCRIS 6493
  • EINECS 208-081-6
  • Giganteumgenin C
  • NSC 114945
  • Oleanic acid
  • Oleanolic acid
  • UNII-6SMK8R7TGJ
  • Virgaureagenin B

Systematic Names

  • 3beta-Hydroxyolean-12-en-28-oic acid
  • Olean-12-en-28-oic acid, 3-beta-hydroxy- (8CI)
  • Olean-12-en-28-oic acid, 3-hydroxy-, (3-beta)-
  • Olean-12-en-28-oic acid, 3-hydroxy-, (3beta)-
  • Olean-12-en-28-oic acid, 3beta-hydroxy- (8CI)
  • Oleanolic acid

Registry Numbers

CAS Registry Number

  • 508-02-1

FDA UNII

  • 6SMK8R7TGJ

Other Registry Number

  • 2088830-42-4

System Generated Number

  • 0000508021

Structure Descriptors

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

InChIKey

MIJYXULNPSFWEK-GTOFXWBISA-N

Smiles

C1[C@@]2([C@@]3(C([C@H]4[C@@](CCC(C4)(C)C)(C(O)=O)CC3)=CC[C@@H]2[C@@]2([C@@H](C([C@@H](O)CC2)(C)C)C1)C)C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1500mg/kg (1500mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 44, Pg. 456, 1992.
mouse LD50 oral > 2gm/kg (2000mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 44, Pg. 456, 1992.
rat LD50 intraperitoneal > 2gm/kg (2000mg/kg)   Drugs of the Future. Vol. 19, Pg. 450, 1994.
rat LD50 oral > 2gm/kg (2000mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 44, Pg. 456, 1992.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 310 dec deg C   EXP
log P (octanol-water) 7.950 (none)   EST
Atmospheric OH Rate Constant 1.23E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.