(3S,3'R,7'aR)-3-hydroxy-3',6',10,11b-tetramethyl-1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-11-one

• ChemBase ID: 172014
• Molecular Formular: C27H39NO3
• Molecular Mass: 425.60346
• Monoisotopic Mass: 425.29299411
• SMILES: [C@H]1(CC2=CCC3C(C2(CC1)C)C(=O)C1=C(C2(CCC31)O[C@H]1C([C@H]2C)NCC(C1)C)C)O
• Canonical SMILES: O[C@H]1CCC2(C(=CCC3C2C(=O)C2=C(C)C4(CCC32)O[C@H]2C([C@H]4C)NCC(C2)C)C1)C
• InChI: InChI=1S/C27H39NO3/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3/t14?,16-,18+,19?,20?,21-,23?,24?,26?,27?/m1/s1
• InChIKey: CLEXYFLHGFJONT-OFBFVVLYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,3'R,7'aR)-3-hydroxy-3',6',10,11b-tetramethyl-1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-11-one
• IUPAC Traditional name: (3S,3'R,7'aR)-3-hydroxy-3',6',10,11b-tetramethyl-1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11a-hexadecahydro-3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-11-one
• Synonyms: (3β,23β)-17,23-Epoxy-3-hydroxyveratraman-11-one; Jervine

Database IDs

• CAS Number: 469-59-0
• PubChem SID: 164227924
• PubChem CID: 45039618

CALCULATED PROPERTIES

• Acid pKa: 18.204275
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.1701644
• LogD (pH = 7.4): 0.927553
• Log P: 3.3851504
• Molar Refractivity: 122.8882 cm^3
• Polarizability: 48.51331 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Off-White to Tan Solid
• Melting Point: 242- 244°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Store in Freezer at - 20°C

DETAILS

Toronto Research Chemicals - J211000

Has antibacterial properties. Jervine demonstrates teratogenic properties. It is the starting material for C-nor-D-homosteroids. Jervine induces holoprosencephaly and blocks endogenous Sonic hedgehog signaling.

REFERENCES

• Cooper, M.K., et al.: Science, 280, 1603 (1998)