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

• ChemBase ID: 127650
• Molecular Formular: C30H48O4
• Molecular Mass: 472.69972
• Monoisotopic Mass: 472.35526002
• SMILES: O=C(O)[C@]12[C@H](C3=CC[C@@H]4[C@@]5([C@@H](CC[C@]4([C@]3(C)CC1)C)[C@](C)(CO)[C@@H](O)CC5)C)CC(C)(C)CC2
• Canonical SMILES: OC[C@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O)C)C
• InChI: InChI=1S/C30H48O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)/t20-,21+,22+,23-,26-,27-,28+,29+,30-/m0/s1
• InChIKey: PGOYMURMZNDHNS-MYPRUECHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
• IUPAC Traditional name: hederagenin
• Synonyms: Hederagenin; Hederagenin; (3β,4α)-3,23-Dihydroxy-olean-12-en-28-oic Acid; Caulosapogenin; Hederagenic Acid; Hederagenine; Hederagenol; NSC 24954

Database IDs

• CAS Number: 465-99-6
• PubChem SID: 162221968
• PubChem CID: 73299
• CHEMBL: 486400
• Chemspider ID: 66038
• Wikipedia Title: Hederagenin

CALCULATED PROPERTIES

• Acid pKa: 4.7442594
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 4.488832
• LogD (pH = 7.4): 2.7118778
• Log P: 5.314062
• Molar Refractivity: 135.3992 cm^3
• Polarizability: 53.8447 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Powder

DETAILS

Toronto Research Chemicals - H129990

Triterpenoid which can inhibit the proliferation of leukemia HL-60 cells.

REFERENCES

• Cho, J., et al.: Pulmon. Pharmacol. Ther., 23, 190 (2010)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010)
• Saha, S., et al.: J. Agric. Food Chem., 58, 434 (2010)