2-amino-3-cyano-4-(3,4,5-trimethoxyphenyl)-4H-naphtho-[1,2-b]pyran

ID: ALA228363

Chembl Id: CHEMBL228363

Cas Number: 339062-56-5

PubChem CID: 2768482

Max Phase: Preclinical

Molecular Formula: C23H20N2O4

Molecular Weight: 388.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C2C(C#N)=C(N)Oc3c2ccc2ccccc32)cc(OC)c1OC

Standard InChI:  InChI=1S/C23H20N2O4/c1-26-18-10-14(11-19(27-2)22(18)28-3)20-16-9-8-13-6-4-5-7-15(13)21(16)29-23(25)17(20)12-24/h4-11,20H,25H2,1-3H3

Standard InChI Key:  QASRNVZBHIVOPA-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA228363

   2-amino-4-(3,4,5-trimethoxyphenyl)-4H-benzo[h]chromene-3-carbonitrile

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: 388.42

Molecular Weight (Monoisotopic): 388.1423

AlogP: 4.08

#Rotatable Bonds: 4

Polar Surface Area: 86.73

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.68

CX LogP: 3.55

CX LogD: 3.55

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.72

Np Likeness Score: -0.54

References

1. Kemnitzer W, Drewe J, Jiang S, Zhang H, Zhao J, Crogan-Grundy C, Xu L, Lamothe S, Gourdeau H, Denis R, Tseng B, Kasibhatla S, Cai SX..  (2007)  Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 3. Structure-activity relationships of fused rings at the 7,8-positions.,  50  (12): [PMID:17497765] [10.1021/jm070216c]

2. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of IQOG CSIS (Spain) compounds,  [10.6019/CHEMBL4513135]

3. Köhler LHF, Reich S, Yusenko M, Klempnauer KH, Shaikh AH, Ahmed K, Begemann G, Schobert R, Biersack B..  (2022)  A New Naphthopyran Derivative Combines c-Myb Inhibition, Microtubule-Targeting Effects, and Antiangiogenic Properties.,  13  (11.0): [PMID:36385941] [10.1021/acsmedchemlett.2c00403]

Source

Source(2):

• Scientific Literature
• CO-ADD antimicrobial screening data