(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,14'R,16'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.02,9.04,8.013,18]icosan]-18'-ene-14',16'-diol

• ChemBase ID: 177659
• Molecular Formular: C27H42O4
• Molecular Mass: 430.61998
• Monoisotopic Mass: 430.30830982
• SMILES: C1[C@@H](CC2=CC[C@@H]3[C@@H]([C@]2([C@@H]1O)C)CC[C@]1([C@H]3C[C@H]2[C@@H]1[C@@H]([C@@]1(O2)OC[C@@H](CC1)C)C)C)O
• Canonical SMILES: C[C@@H]1CC[C@@]2(OC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC=C3[C@]([C@H]1CC2)(C)[C@H](O)C[C@@H](C3)O)C
• InChI: InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)13-21-19-6-5-17-11-18(28)12-23(29)26(17,4)20(19)8-9-25(21,24)3/h5,15-16,18-24,28-29H,6-14H2,1-4H3/t15-,16+,18-,19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1
• InChIKey: QMQIQBOGXYYATH-IDABPMKMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,14'R,16'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosan]-18'-ene-14',16'-diol
• IUPAC Traditional name: ruscogenin
• Synonyms: (1β,3β,25R)-Spirost-5-ene-1,3-diol; (25R)-Spirost-5-ene-1β,3β-diol; 25D-Spirost-5-ene-1β,3β-diol; Ruscogenin

Database IDs

• CAS Number: 472-11-7
• PubChem SID: 164233569
• PubChem CID: 441893

CALCULATED PROPERTIES

• Acid pKa: 14.449436
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.6237004
• LogD (pH = 7.4): 3.6237004
• Log P: 3.6237004
• Molar Refractivity: 121.7378 cm^3
• Polarizability: 48.465572 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R701750

A major steroidal sapogenin from Radix ophiopogon japonicus with robust anti-inflammatory and anti-thrombotic activities. Studies suggest that it inhibits adhesion of leukocytes to a human umbilical vein endothelial cell line (ECV304) injured by tumor nec

REFERENCES

• Huang, Y. et al.: Drug Dev. Res., 69, 196 (2008)
• Huang, Y. et al.: J. Pharmacol. Sci., 108, 198 (2008)
• Song, J. et al.: J. Pharmacol. Sci., 113, 409 (2008)