1-(3,4-Dimethoxy-phenyl)-3-[2-(3,4-dimethoxy-phenyl)-ethyl]-7,8-dimethoxy-3H-chromeno[3,4-b]pyrrol-4-one

ID: ALA50150

Chembl Id: CHEMBL50150

PubChem CID: 10187365

Max Phase: Preclinical

Molecular Formula: C31H31NO8

Molecular Weight: 545.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CCn2cc(-c3ccc(OC)c(OC)c3)c3c4cc(OC)c(OC)cc4oc(=O)c32)cc1OC

Standard InChI:  InChI=1S/C31H31NO8/c1-34-22-9-7-18(13-25(22)36-3)11-12-32-17-21(19-8-10-23(35-2)26(14-19)37-4)29-20-15-27(38-5)28(39-6)16-24(20)40-31(33)30(29)32/h7-10,13-17H,11-12H2,1-6H3

Standard InChI Key:  NACJRCSRBMFCJQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA50150

   1-(3,4-Dimethoxyphenyl)-3-[2-(3,4-dimethoxyphenyl)ethyl]-7,8-dimethoxychromeno[3,4-b]pyrrol-4-one

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: 545.59

Molecular Weight (Monoisotopic): 545.2050

AlogP: 5.71

#Rotatable Bonds: 10

Polar Surface Area: 90.52

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.86

CX LogD: 4.86

Aromatic Rings: 5

Heavy Atoms: 40

QED Weighted: 0.21

Np Likeness Score: 0.04

References

1. Soenen DR, Hwang I, Hedrick MP, Boger DL..  (2003)  Multidrug resistance reversal activity of key ningalin analogues.,  13  (10): [PMID:12729663] [10.1016/s0960-894x(03)00294-4]

2. Tao H, Hwang I, Boger DL..  (2004)  Multidrug resistance reversal activity of permethyl ningalin B amide derivatives.,  14  (24): [PMID:15546712] [10.1016/j.bmcl.2004.10.002]

3. Joshi P, Vishwakarma RA, Bharate SB..  (2017)  Natural alkaloids as P-gp inhibitors for multidrug resistance reversal in cancer.,  138  [PMID:28675836] [10.1016/j.ejmech.2017.06.047]

4. Salehian F, Nadri H, Jalili-Baleh L, Youseftabar-Miri L, Abbas Bukhari SN, Foroumadi A, Tüylü Küçükkilinç T, Sharifzadeh M, Khoobi M..  (2021)  A review: Biologically active 3,4-heterocycle-fused coumarins.,  212  [PMID:33276991] [10.1016/j.ejmech.2020.113034]

Source

Source(1):

• Scientific Literature