methyl (2E)-2-[(2S,4S,5R,10S)-5-ethyl-10-hydroxy-12-methoxy-7,17-diazatetracyclo[8.7.0.02,7.011,16]heptadeca-1(17),11,13,15-tetraen-4-yl]-3-methoxyprop-2-enoate

• ChemBase ID: 170853
• Molecular Formular: C23H30N2O5
• Molecular Mass: 414.4947
• Monoisotopic Mass: 414.21547207
• SMILES: c1ccc2c(c1OC)[C@@]1(C(=N2)[C@H]2N(CC1)C[C@@H]([C@H](C2)/C(=C\OC)/C(=O)OC)CC)O
• Canonical SMILES: CO/C=C(\[C@H]1C[C@@H]2N(C[C@@H]1CC)CC[C@]1(C2=Nc2c1c(OC)ccc2)O)/C(=O)OC
• InChI: InChI=1S/C23H30N2O5/c1-5-14-12-25-10-9-23(27)20-17(7-6-8-19(20)29-3)24-21(23)18(25)11-15(14)16(13-28-2)22(26)30-4/h6-8,13-15,18,27H,5,9-12H2,1-4H3/b16-13+/t14-,15-,18-,23-/m0/s1
• InChIKey: RYENLSMHLCNXJT-ZHOKILCHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2E)-2-[(2S,4S,5R,10S)-5-ethyl-10-hydroxy-12-methoxy-7,17-diazatetracyclo[8.7.0.0^2,^7.0^1^1,^1^6]heptadeca-1(17),11,13,15-tetraen-4-yl]-3-methoxyprop-2-enoate
• IUPAC Traditional name: methyl (2E)-2-[(2S,4S,5R,10S)-5-ethyl-10-hydroxy-12-methoxy-7,17-diazatetracyclo[8.7.0.0^2,^7.0^1^1,^1^6]heptadeca-1(17),11,13,15-tetraen-4-yl]-3-methoxyprop-2-enoate
• Synonyms: 7-Hydroxy Mitragynine; (αE,2S,3S,7aS,12bS)-3-Ethyl-1,2,3,4,6,7,7a,12b-octahydro-7a-hydroxy-8-methoxy-α-(methoxymethylene)indolo[2,3-a]quinolizine-2-acetic Acid Methyl Ester; (7α,16E,20β)-1,2,16,17-Tetradehydro-2,7-dihydro-7-hydroxy-9,17-dimethoxycorynan-16-carboxylic acid Methyl Ester; 7α-Hydroxy-7H-mitragynine; 9-Methoxycorynantheidine Hydroxyindolenine; Mitragynine Hydroxyindolenine

Database IDs

• CAS Number: 174418-82-7
• PubChem SID: 164226763
• PubChem CID: 71749158

CALCULATED PROPERTIES

• Acid pKa: 12.473693
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.9340694
• LogD (pH = 7.4): 2.4871814
• Log P: 2.7483537
• Molar Refractivity: 115.3466 cm^3
• Polarizability: 44.200966 Å^3
• Polar Surface Area: 80.59 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H947910

A metabolite of Mitragynine as analgesic agents.

REFERENCES

• Gyand, E., et al.: Br. J. Pharmacol., 27, 514 (1966)
• Shellard, E., et al.: Planta Med., 34, 253 (1966)
• Takayama, H., et al.: Chem. Pharm. Bull., 52, 916 (1966)