methyl (2E)-2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

• ChemBase ID: 177712
• Molecular Formular: C23H30N2O4
• Molecular Mass: 398.4953
• Monoisotopic Mass: 398.22055745
• SMILES: c12c(CCN3[C@@H]1C[C@@H]([C@@H](C3)CC)/C(=C\OC)/C(=O)OC)c1c([nH]2)cccc1OC
• Canonical SMILES: CO/C=C(\[C@H]1C[C@H]2N(C[C@H]1CC)CCc1c2[nH]c2c1c(OC)ccc2)/C(=O)OC
• InChI: InChI=1S/C23H30N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14-,16+,19-/m1/s1
• InChIKey: LELBFTMXCIIKKX-MYLQJJOTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2E)-2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
• IUPAC Traditional name: methyl (2E)-2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
• Synonyms: (αE,2S,3S,12bR)-3-ethyl-1,2,3,4,6,7,12,12b-octahydro-8-methoxy-α-(methoxymethylene)indolo[2,3-a]quinolizine-2-acetic Acid Methyl Ester; Speciociliatin; (3β,16E,20β)-16,17-Didehydro-9,17-dimethoxycorynan-16-carboxylic Acid Methyl Ester; (E)-16,17-Didehydro-9,17-dimethoxy-17,18-seco-3β,20α-yohimban-16-carboxylic Acid Methyl Ester; Speciociliatine

Database IDs

• CAS Number: 14382-79-7
• PubChem SID: 164233622
• PubChem CID: 15560576

CALCULATED PROPERTIES

• Acid pKa: 16.670277
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.4754633
• LogD (pH = 7.4): 3.0337396
• Log P: 3.2995937
• Molar Refractivity: 112.9132 cm^3
• Polarizability: 45.03689 Å^3
• Polar Surface Area: 63.79 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S680100

Speciociliatine is an epimer of Mitragynine (M373550). Speciociliatine is an indole alkaloid from Mitragyna speciosa used in natural medicine. Speciociliatine is a neurochemical with opioid agonistic activity.

REFERENCES

• Kitajima, M. et al.: J. Nat. Med., 60, 28 (2006)
• Horie, S. et al.: Planta Med., 71, 231 (2006)
• Takayama, H. et al.: J. Med. Chem., 45, 1949 (2006)