(2S,3R,5S)-2-[(1S)-1-[(3S,6aR,11aS,11bR)-3-hydroxy-10,11b-dimethyl-1H,2H,3H,4H,6H,6aH,11H,11aH,11bH-cyclohexa[a]fluoren-9-yl]ethyl]-5-methylpiperidin-3-ol

• ChemBase ID: 179493
• Molecular Formular: C27H39NO2
• Molecular Mass: 409.60406
• Monoisotopic Mass: 409.29807949
• SMILES: C1[C@H]2[C@H](c3c1c(c(cc3)[C@@H]([C@H]1[C@@H](C[C@@H](CN1)C)O)C)C)CC=C1[C@@]2(CC[C@@H](C1)O)C
• Canonical SMILES: C[C@@H]1CN[C@H]([C@@H](C1)O)[C@H](c1ccc2c(c1C)C[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)C
• InChI: InChI=1S/C27H39NO2/c1-15-11-25(30)26(28-14-15)17(3)20-7-8-21-22-6-5-18-12-19(29)9-10-27(18,4)24(22)13-23(21)16(20)2/h5,7-8,15,17,19,22,24-26,28-30H,6,9-14H2,1-4H3/t15-,17-,19-,22-,24-,25+,26-,27-/m0/s1
• InChIKey: MALFODICFSIXPO-KFKQDBFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,5S)-2-[(1S)-1-[(3S,6aR,11aS,11bR)-3-hydroxy-10,11b-dimethyl-1H,2H,3H,4H,6H,6aH,11H,11aH,11bH-cyclohexa[a]fluoren-9-yl]ethyl]-5-methylpiperidin-3-ol
• IUPAC Traditional name: (2S,3R,5S)-2-[(1S)-1-[(3S,6aR,11aS,11bR)-3-hydroxy-10,11b-dimethyl-1H,2H,3H,4H,6H,6aH,11H,11aH-cyclohexa[a]fluoren-9-yl]ethyl]-5-methylpiperidin-3-ol
• Synonyms: (3β,23β)-14,15,16,17-Teradehydroveratraman-3,23-diol; NSC 17821; NSC 23880; Veratramine

Database IDs

• CAS Number: 60-70-8
• PubChem SID: 164235403
• PubChem CID: 6070

CALCULATED PROPERTIES

• Acid pKa: 14.57388
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 1.199474
• LogD (pH = 7.4): 1.9728489
• Log P: 4.4131866
• Molar Refractivity: 124.0889 cm^3
• Polarizability: 48.31698 Å^3
• Polar Surface Area: 52.49 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 198-200°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - V127500

It is useful as signal transduction inhibitor for treating tumors.

REFERENCES

• Imamura, L., et al.: J. Trad. Med., 12, 129 (1995)
• Ingolfsdottir, K., et al.: Antimicrob. Agents. Chemother., 1997, 41, 215 (1995)
• Tezuka, Y., et al.: J. Nat. Prod., 61, 1397 (1988)