(1S)-21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15(20),16,18-heptaen-14-one

• ChemBase ID: 119807
• Molecular Formular: C19H17N3O
• Molecular Mass: 303.35778
• Monoisotopic Mass: 303.13716218
• SMILES: N12[C@@H](c3c(c4c([nH]3)cccc4)CC2)N(c2c(C1=O)cccc2)C
• Canonical SMILES: O=C1c2ccccc2N([C@H]2N1CCc1c2[nH]c2c1cccc2)C
• InChI: InChI=1S/C19H17N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9,18,20H,10-11H2,1H3/t18-/m0/s1
• InChIKey: TXDUTHBFYKGSAH-SFHVURJKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-21-methyl-3,13,21-triazapentacyclo[11.8.0.0^2,^1^0.0^4,^9.0^1^5,^2^0]henicosa-2(10),4,6,8,15(20),16,18-heptaen-14-one
• IUPAC Traditional name: evodiamine; (1S)-21-methyl-3,13,21-triazapentacyclo[11.8.0.0^2,^1^0.0^4,^9.0^1^5,^2^0]henicosa-2(10),4,6,8,15(20),16,18-heptaen-14-one
• Synonyms: (S)-14-methyl-7,8,13b,14-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(13H)-one; (13bS)-8,13,13b-14-Tetrahydro-14-methyl-indolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one; d-Evodiamine; (+)-Evodiamine; Evodiamine; Evodiamine

Database IDs

• CAS Number: 518-17-2
• PubChem SID: 162108178
• PubChem CID: 442088

CALCULATED PROPERTIES

• Acid pKa: 14.914593
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.31676
• LogD (pH = 7.4): 3.31676
• Log P: 3.31676
• Molar Refractivity: 91.0132 cm^3
• Polarizability: 35.02149 Å^3
• Polar Surface Area: 39.34 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Pale Yellow Solid; Powder
• Melting Point: >240°C (dec.)

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Mechanism of Action: May interact with UCP1, which is a thermogenic protein that allows energy to be burned as heat

Product Information

• Biological Source: A major component of the Chinese drug Wou-chou-yu (the dried fruit of Evodia rutaecarpa ). Also present in Araliopsis tabouensis (Rutaceae, Araliaceae)
• Application(s): Diuretic and diaphoretic agent

DETAILS

Toronto Research Chemicals - E945480

A chemical extracted from Evodia plants, and has been shown to reduce fat uptake.

REFERENCES

• Yu, P., et al.: J. Cell. Biochem., 108, 469 (2009)
• Yang, Z., et al.: Chemi. Biodivers., 6, 924 (2009)
• Hibino, T., et al.: Biol. Pharm. Bull., 32, 237 (2009)
• Chatterjee, A. et al., Tetrahedron, 1959, 7, 257, (isol)
• Gopinath, K.W. et al., Tetrahedron, 1960, 8, 293, (isol)
• Yamazaki, M. et al., Tet. Lett., 1966, 3221; 1967, 3317, (biosynth)
• Tams, J. et al., Acta Chim. Acad. Sci. Hung., 1976, 89, 85, (ms)
• Kametani, T. et al., J.A.C.S., 1976, 98, 6186, (synth, ir, uv, pmr, ms)
• Danieli, B. et al., Heterocycles, 1978, 9, 803, (synth)
• Danieli, B. et al., Experientia, 1979, 35, 156, (isol, uv, cd, ir, pmr, ms, abs config, synth, 7-Carboxyevodiamine)
• Danieli, B. et al., Chem. Comm., 1982, 1092, (synth, cd, abs config)
• Bergman, J. et al., J.O.C., 1985, 50, 1246, (synth)
• Kobayashi, Y. et al., Planta Med., 2000, 66, 526-530, (activity)