(Z)-2-(2,3-Diamino-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethene

ID: ALA256278

Chembl Id: CHEMBL256278

PubChem CID: 24854276

Max Phase: Preclinical

Molecular Formula: C18H22N2O4

Molecular Weight: 330.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)c(N)c1N

Standard InChI:  InChI=1S/C18H22N2O4/c1-21-13-8-7-12(16(19)17(13)20)6-5-11-9-14(22-2)18(24-4)15(10-11)23-3/h5-10H,19-20H2,1-4H3/b6-5-

Standard InChI Key:  CTJFAGXSJGHOGY-WAYWQWQTSA-N

Alternative Forms

1. Alternative Forms:

   

   ALA256278

   3-methoxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]benzene-1,2-diamine;dihydrochloride

2. Parent:

   

   ALA256278

   2',3'-Diamino-3,4,4',5-tetramethoxy-(Z)-stilbene
3. 

   ALA256278

   3-methoxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]benzene-1,2-diamine;hydrochloride

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 330.38

Molecular Weight (Monoisotopic): 330.1580

AlogP: 3.06

#Rotatable Bonds: 6

Polar Surface Area: 88.96

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.97

CX LogP: 2.02

CX LogD: 2.02

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.62

Np Likeness Score: 0.50

References

1. Siles R, Ackley JF, Hadimani MB, Hall JJ, Mugabe BE, Guddneppanavar R, Monk KA, Chapuis JC, Pettit GR, Chaplin DJ, Edvardsen K, Trawick ML, Garner CM, Pinney KG..  (2008)  Combretastatin dinitrogen-substituted stilbene analogues as tubulin-binding and vascular-disrupting agents.,  71  (3): [PMID:18303849] [10.1021/np070377j]

2. Devkota L, Lin CM, Strecker TE, Wang Y, Tidmore JK, Chen Z, Guddneppanavar R, Jelinek CJ, Lopez R, Liu L, Hamel E, Mason RP, Chaplin DJ, Trawick ML, Pinney KG..  (2016)  Design, synthesis, and biological evaluation of water-soluble amino acid prodrug conjugates derived from combretastatin, dihydronaphthalene, and benzosuberene-based parent vascular disrupting agents.,  24  (5): [PMID:26852340] [10.1016/j.bmc.2016.01.007]

Source

Source(1):

• Scientific Literature