(1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.02,10.05,9.014,19]henicosane-5-carboxylic acid

• ChemBase ID: 162024
• Molecular Formular: C30H48O3
• Molecular Mass: 456.70032
• Monoisotopic Mass: 456.3603454
• SMILES: C1[C@@H](C([C@H]2[C@](C1)([C@@H]1[C@@](CC2)([C@]2([C@H](CC1)[C@@H]1[C@@](CC2)(CC[C@H]1C(=C)C)C(=O)O)C)C)C)(C)C)O
• Canonical SMILES: CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C(=O)O
• InChI: InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
• InChIKey: QGJZLNKBHJESQX-FZFNOLFKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^2,^1^0.0^5,^9.0^1^4,^1^9]henicosane-5-carboxylic acid
• IUPAC Traditional name: mairin
• Synonyms: Mairin; (+)-Betulinic acid; 3β-Hydroxylup-20(29)-en-28-oic Acid; Betulic Acid; Lupatic Acid; NSC 113090; β-Betulinic Acid; (3β)-3-HydroxyLup-20(29)-en-28-oic Acid; Betulinic Acid

Database IDs

• CAS Number: 472-15-1
• PubChem SID: 162256159
• PubChem CID: 64971

CALCULATED PROPERTIES

• Acid pKa: 4.7483134
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.817948
• LogD (pH = 7.4): 4.041123
• Log P: 6.639739
• Molar Refractivity: 132.6255 cm^3
• Polarizability: 53.23124 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B330250

Betulinic Acid is a natural pentacyclic triterpenoid. Betulinic Acid displays anti-inflammatory and anti-HIV activity. Betulinic Acid selectively induces apoptosis in tumor cells by directly activating the mitochondrial pathway of apoptosis through a p53

REFERENCES

• Pisha, E. et al.: Nat. Med., 1, 1046 (1995)
• Fulda, S. et al.: Cancer Res., 57, 4956 (1995)
• Kashiwada, Y. et al.: J. Med. Chem., 39, 1016 (1995)
• Genet, C. et al.: J. Med. Chem., 53, 178 (1995)