CAS 518-17-2|evodiamine|(1S)-21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2...

General Information

Structure

Molecular Formula

C₁₉H₁₇N₃O

Molecular Mass

303.35778

Exact Mass

303.13716218

Charge

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

Canonic Smiles

O=C1c2ccccc2N([C@H]2N1CCc1c2[nH]c2c1cccc2)C

Isomeric Smiles

N12[C@@H](c3c(c4c([nH]3)cccc4)CC2)N(c2c(C1=O)cccc2)C

Calculated Properties

JChem

Acid pKa

14.914593

H Acceptors

H Donor

LogD (pH = 5.5)

3.31676

LogD (pH = 7.4)

3.31676

Log P

3.31676

Molar Refractivity

91.0132

Polarizability

35.02149

Polar Surface Area

39.34

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

IUPAC Traditional name

evodiamine (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

IUPAC name

(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

Synonyms

Evodiamined-EvodiamineEvodiamine(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(+)-Evodiamine

Names and Identifiers

Registration numbers

PubChem CID

442088

PubChem SID

162108178

CAS Number

518-17-2

Registration numbers

Properties

Safety Information

Storage Condition

Refrigerator

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Product Information

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Diuretic and diaphoretic agent

A major component of the Chinese drug Wou-chou-yu (the dried fruit of Evodia rutaecarpa ). Also present in Araliopsis tabouensis (Rutaceae, Araliaceae)

Pharmacology Properties

May interact with UCP1, which is a thermogenic protein that allows energy to be burned as heat

Properties

Related Proteins

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Molecular Spectra

No Data Available

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Molecule Details

TRC

E945480

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

Molecule Details

References

PubChem Literature

From Data Sources

• Hibino, T., et al.: Biol. Pharm. Bull., 32, 237 (2009)

• Yang, Z., et al.: Chemi. Biodivers., 6, 924 (2009)

• Yu, P., et al.: J. Cell. Biochem., 108, 469 (2009)

• Chatterjee, A. et al., Tetrahedron, 1959, 7, 257, (isol)

• Gopinath, K.W. et al., Tetrahedron, 1960, 8, 293, (isol)

• Danieli, B. et al., Heterocycles, 1978, 9, 803, (synth)

• Yamazaki, M. et al., Tet. Lett., 1966, 3221; 1967, 3317, (biosynth)

• Danieli, B. et al., Chem. Comm., 1982, 1092, (synth, cd, abs config)

• Danieli, B. et al., Experientia, 1979, 35, 156, (isol, uv, cd, ir, pmr, ms, abs config, synth, 7-Carboxyevodiamine)

• Kobayashi, Y. et al., Planta Med., 2000, 66, 526-530, (activity)

• 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)

• Bergman, J. et al., J.O.C., 1985, 50, 1246, (synth)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Commercial Catalog

Academic Data

Names and Identifiers

IUPAC Traditional name

evodiamine (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

IUPAC name

(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

Synonyms

Registration numbers

PubChem CID

PubChem SID

CAS Number

Molecule Details

E945480

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

References

PubChem Literature

From Data Sources

• Hibino, T., et al.: Biol. Pharm. Bull., 32, 237 (2009)

• Yang, Z., et al.: Chemi. Biodivers., 6, 924 (2009)

• Yu, P., et al.: J. Cell. Biochem., 108, 469 (2009)

• Chatterjee, A. et al., Tetrahedron, 1959, 7, 257, (isol)

• Gopinath, K.W. et al., Tetrahedron, 1960, 8, 293, (isol)

• Danieli, B. et al., Heterocycles, 1978, 9, 803, (synth)

• Yamazaki, M. et al., Tet. Lett., 1966, 3221; 1967, 3317, (biosynth)

• Danieli, B. et al., Chem. Comm., 1982, 1092, (synth, cd, abs config)

• Danieli, B. et al., Experientia, 1979, 35, 156, (isol, uv, cd, ir, pmr, ms, abs config, synth, 7-Carboxyevodiamine)

• Kobayashi, Y. et al., Planta Med., 2000, 66, 526-530, (activity)

• 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)

• Bergman, J. et al., J.O.C., 1985, 50, 1246, (synth)

Bioactivity

PubChem BioAssay

Properties

Safety Information

Storage Condition

Refrigerator

Download link

Product Information

Download link

Diuretic and diaphoretic agent

A major component of the Chinese drug Wou-chou-yu (the dried fruit of Evodia rutaecarpa ). Also present in Araliopsis tabouensis (Rutaceae, Araliaceae)

Pharmacology Properties

May interact with UCP1, which is a thermogenic protein that allows energy to be burned as heat

Molecule

ID:119807