methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-9-hydroxy-6a,10b-dimethyl-4,10-dioxo-dodecahydro-1H-naphtho[2,1-c]pyran-7-carboxylate

• ChemBase ID: 154603
• Molecular Formular: C21H26O7
• Molecular Mass: 390.42694
• Monoisotopic Mass: 390.16785317
• SMILES: C[C@@]12CC[C@H]3C(=O)O[C@@H](C[C@@]3([C@H]1C(=O)[C@H](C[C@H]2C(=O)OC)O)C)c1ccoc1
• Canonical SMILES: COC(=O)[C@@H]1C[C@H](O)C(=O)[C@H]2[C@@]1(C)CC[C@@H]1[C@]2(C)C[C@H](OC1=O)c1cocc1
• InChI: InChI=1S/C21H26O7/c1-20-6-4-12-19(25)28-15(11-5-7-27-10-11)9-21(12,2)17(20)16(23)14(22)8-13(20)18(24)26-3/h5,7,10,12-15,17,22H,4,6,8-9H2,1-3H3/t12-,13-,14-,15-,17-,20-,21-/m0/s1
• InChIKey: BLTMVAIOAAGYAR-CEFSSPBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-9-hydroxy-6a,10b-dimethyl-4,10-dioxo-dodecahydro-1H-naphtho[2,1-c]pyran-7-carboxylate
• IUPAC Traditional name: methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-9-hydroxy-6a,10b-dimethyl-4,10-dioxo-octahydro-1H-naphtho[2,1-c]pyran-7-carboxylate
• Synonyms: (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(3-Furanyl)dodecahydro-9-hydroxy-6a,10b-dimethyl-4,10-dioxo 2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester; Divinorin B; Salvinorin B; (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(3-Furanyl)dodecahydro-9-hydroxy-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic Acid Methyl Ester; [2S-(2α,4aα,6aβ,7β,9β,10aα,10bβ)]-2-(3-Furanyl)dodecahydro-9-hydroxy-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic Acid Methyl Ester; (-)-Salvinorin B; Salvinorin B

Database IDs

• CAS Number: 92545-30-7
• MDL Number: MFCD16036232
• Beilstein Number: 4335292
• PubChem SID: 162248741
• PubChem CID: 11440685

CALCULATED PROPERTIES

• Acid pKa: 13.368622
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.9478885
• LogD (pH = 7.4): 1.947888
• Log P: 1.9478885
• Molar Refractivity: 96.8439 cm^3
• Polarizability: 38.64345 Å^3
• Polar Surface Area: 103.04 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥93.0% (HPLC)
• Empirical Formula (Hill Notation): C21H26O7

DETAILS

Toronto Research Chemicals - S100920

Salvinorin B is a metabolite of Salvinorin A (S100900), a hallucinogen.

REFERENCES

• Tougou, K., et al.: Drug Metab. Disposit., 26, 355 (1998)
• Teiber, J., et al.: Biochem. Pharmacol., 2003, 66, 887 (1998)
• Yamaori, S., et al.: Drug Metab. Pharmacokinet., 21, 147 (1998)