(Z)-2-(2-(2-methoxy-5-(3,4,5-trimethoxystyryl)phenoxy)propan-2-yl)-5-nitrothiophene

ID: ALA4094475

Chembl Id: CHEMBL4094475

PubChem CID: 11752085

Max Phase: Preclinical

Molecular Formula: C25H27NO7S

Molecular Weight: 485.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)cc1OC(C)(C)c1ccc([N+](=O)[O-])s1

Standard InChI:  InChI=1S/C25H27NO7S/c1-25(2,22-11-12-23(34-22)26(27)28)33-19-13-16(9-10-18(19)29-3)7-8-17-14-20(30-4)24(32-6)21(15-17)31-5/h7-15H,1-6H3/b8-7-

Standard InChI Key:  WZSKVKFBTMLUAY-FPLPWBNLSA-N

Alternative Forms

1. Parent:

   

   ALA4094475

   2-[2-[2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenoxy]propan-2-yl]-5-nitrothiophene

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: 485.56

Molecular Weight (Monoisotopic): 485.1508

AlogP: 6.18

#Rotatable Bonds: 10

Polar Surface Area: 89.29

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.97

CX LogD: 5.97

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.19

Np Likeness Score: -0.27

References

1. Winn BA, Shi Z, Carlson GJ, Wang Y, Nguyen BL, Kelly EM, Ross RD, Hamel E, Chaplin DJ, Trawick ML, Pinney KG..  (2017)  Bioreductively activatable prodrug conjugates of phenstatin designed to target tumor hypoxia.,  27  (3): [PMID:28007448] [10.1016/j.bmcl.2016.11.093]

2. Winn BA, Devkota L, Kuch B, MacDonough MT, Strecker TE, Wang Y, Shi Z, Gerberich JL, Mondal D, Ramirez AJ, Hamel E, Chaplin DJ, Davis P, Mason RP, Trawick ML, Pinney KG..  (2020)  Bioreductively Activatable Prodrug Conjugates of Combretastatin A-1 and Combretastatin A-4 as Anticancer Agents Targeted toward Tumor-Associated Hypoxia.,  83  (4): [PMID:32196334] [10.1021/acs.jnatprod.9b00773]

Source

Source(1):

• Scientific Literature