methyl (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-11-oxo-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]-4'-carboxylate

• ChemBase ID: 179492
• Molecular Formular: C29H41NO5
• Molecular Mass: 483.63954
• Monoisotopic Mass: 483.29847342
• SMILES: C1[C@@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)C(=O)C1=C([C@@]2(CC[C@@H]31)[C@@H]([C@H]1[C@@H](C[C@@H](CN1C(=O)OC)C)O2)C)C)O
• Canonical SMILES: COC(=O)N1C[C@@H](C)C[C@@H]2[C@@H]1[C@@H](C)[C@]1(O2)CC[C@@H]2C(=C1C)C(=O)[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O
• InChI: InChI=1S/C29H41NO5/c1-15-12-22-25(30(14-15)27(33)34-5)17(3)29(35-22)11-9-20-21-7-6-18-13-19(31)8-10-28(18,4)24(21)26(32)23(20)16(29)2/h6,15,17,19-22,24-25,31H,7-14H2,1-5H3/t15-,17+,19-,20-,21-,22+,24+,25-,28-,29-/m0/s1
• InChIKey: BSYVNBXLPWSHPA-VFVYFEGOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-11-oxo-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]-4'-carboxylate
• IUPAC Traditional name: methyl (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-11-oxo-1,2,3,3',3'a,4,5',6,6',6a,6b,7,7',7'a,8,11a-hexadecahydrospiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-4'-carboxylate
• Synonyms: (2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-1,2,3,3',3'a,4,5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-Octadecahydro-3-hydroxy-3',6',10,11b-tetramethyl-11-oxo-spiro[9H-benzo[a]fluorene-9,2'(4'H)-furo[3,2-b]pyridine]-4'-carboxylic Acid Methyl Ester; Verapatuline

Database IDs

• CAS Number: 212968-58-6
• PubChem SID: 164235402
• PubChem CID: 10528844

CALCULATED PROPERTIES

• Acid pKa: 18.204275
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.6143837
• LogD (pH = 7.4): 3.614384
• Log P: 3.614384
• Molar Refractivity: 134.0777 cm^3
• Polarizability: 52.580864 Å^3
• Polar Surface Area: 76.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White Solid
• Melting Point: 235-237°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - V126700

A new steroidal alkaloid from the Roots and Rhizomes of Veratrum patulum.

REFERENCES

• Zhao, W., et al.: Chem. Pharm. Bull., 39, 549 (1991)
• Han, X., et al.: Planta Med., 58, 449 (1991)