ID: ALA200148

Max Phase: Preclinical

Molecular Formula: C21H13N5O3

Molecular Weight: 383.37

Molecule Type: Small molecule

Representations

Canonical SMILES:  N=C1C=C(O)c2ccc(-c3nc(C(N)=O)cc4c3[nH]c3ccccc34)nc2C1=O

Standard InChI:  InChI=1S/C21H13N5O3/c22-12-8-16(27)10-5-6-14(25-18(10)20(12)28)19-17-11(7-15(26-19)21(23)29)9-3-1-2-4-13(9)24-17/h1-8,22,24,27H,(H2,23,29)

Standard InChI Key:  UOASSCVCKGCNIO-UHFFFAOYSA-N

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

Properties

Molecular Weight: 383.37

Molecular Weight (Monoisotopic): 383.1018

AlogP: 2.99

#Rotatable Bonds: 2

Polar Surface Area: 145.81

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 5.64

CX Basic pKa: 2.42

CX LogP: 2.19

CX LogD: 0.46

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.42

Np Likeness Score: 0.36

References

1. Hassani M, Cai W, Holley DC, Lineswala JP, Maharjan BR, Ebrahimian GR, Seradj H, Stocksdale MG, Mohammadi F, Marvin CC, Gerdes JM, Beall HD, Behforouz M..  (2005)  Novel lavendamycin analogues as antitumor agents: synthesis, in vitro cytotoxicity, structure-metabolism, and computational molecular modeling studies with NAD(P)H:quinone oxidoreductase 1.,  48  (24): [PMID:16302813] [10.1021/jm050758z]

2. Hassani M, Cai W, Koelsch KH, Holley DC, Rose AS, Olang F, Lineswala JP, Holloway WG, Gerdes JM, Behforouz M, Beall HD..  (2008)  Lavendamycin antitumor agents: structure-based design, synthesis, and NAD(P)H:quinone oxidoreductase 1 (NQO1) model validation with molecular docking and biological studies.,  51  (11): [PMID:18457384] [10.1021/jm701066a]

3. Cai W, Hassani M, Karki R, Walter ED, Koelsch KH, Seradj H, Lineswala JP, Mirzaei H, York JS, Olang F, Sedighi M, Lucas JS, Eads TJ, Rose AS, Charkhzarrin S, Hermann NG, Beall HD, Behforouz M..  (2010)  Synthesis, metabolism and in vitro cytotoxicity studies on novel lavendamycin antitumor agents.,  18  (5): [PMID:20149966] [10.1016/j.bmc.2010.01.037]

Source

Source(1):

• Scientific Literature