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

• ChemBase ID: 176251
• Molecular Formular: C27H41NO3
• Molecular Mass: 427.61934
• Monoisotopic Mass: 427.30864418
• SMILES: C1[C@@H](C[C@H]2[C@](C1)([C@@H]1[C@@H](CC2=O)[C@H]2C(=C([C@]3(CC2)O[C@@H]2C[C@@H](CNC2[C@H]3C)C)C)C1)C)O
• Canonical SMILES: O[C@H]1CC[C@]2([C@H](C1)C(=O)C[C@@H]1[C@@H]2CC2=C(C)[C@]3(CC[C@@H]12)O[C@H]1C([C@H]3C)NC[C@H](C1)C)C
• InChI: InChI=1S/C27H41NO3/c1-14-9-24-25(28-13-14)16(3)27(31-24)8-6-18-19(15(27)2)11-21-20(18)12-23(30)22-10-17(29)5-7-26(21,22)4/h14,16-18,20-22,24-25,28-29H,5-13H2,1-4H3/t14-,16+,17-,18+,20-,21-,22+,24+,25?,26+,27-/m0/s1
• InChIKey: KYELXPJVGNZIGC-XSKZRVOTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,3'R,4aS,6'S,6aR,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-1,2,3,3'a,4,4',4a,5,5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-icosahydro-3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-5-one
• IUPAC Traditional name: (3S,3'R,4aS,6'S,6aR,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-1,2,3,3'a,4,4',4a,5',6,6',6a,6b,7,7',7'a,8,11,11a-octadecahydro-3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-5-one
• Synonyms: (3β)-17,23-Epoxy-3-hydroxyveratraman-6(5H)-one; (-)-Ebeiensine; 11-Deoxo-6-oxo-5α,6-dihydrojervine; Ebeiensine; Peimisine; (2'R,3S,3'R,3'aS,4aS,6'S,6aR,6bS,7'aR,11aS,11bR)-1,2,3,3'a,4,4',4a,5',6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3-hydroxy-3',6',10,11b-tetramethylspiro[9H-benzo[a]fluorene-9,2'(3'H)-furo[3,2-b]pyridin]-5(6H)-one

Database IDs

• CAS Number: 19773-24-1
• PubChem SID: 164232161
• PubChem CID: 71751476

CALCULATED PROPERTIES

• Acid pKa: 15.234279
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.06380906
• LogD (pH = 7.4): 0.8211909
• Log P: 3.2787955
• Molar Refractivity: 121.9864 cm^3
• Polarizability: 48.753742 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P218400

An alkaloid FR 5 from Fritillaria thunbergii. An angiotensin converting enzyme inhibitory steroidal alkaloid. It is a commonly used antitussive and expectorant herb in traditional Chinese medicine.

REFERENCES

• Gilani, A., et al.: Life Sci., 60, 535 (1997)
• Jiang, Y., et al.: J. Nat. Prod., 68, 264 (1997)
• Jiang, Y., et al.: Steroids, 71, 843 (1997)