ID: ALA73067

Max Phase: Preclinical

Molecular Formula: C11H11NO4

Molecular Weight: 221.21

Molecule Type: Small molecule

Representations

Canonical SMILES:  COC1=CC(=O)c2c(c(CO)cn2C)C1=O

Standard InChI:  InChI=1S/C11H11NO4/c1-12-4-6(5-13)9-10(12)7(14)3-8(16-2)11(9)15/h3-4,13H,5H2,1-2H3

Standard InChI Key:  QJWLNCMCUSDNQQ-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: 221.21

Molecular Weight (Monoisotopic): 221.0688

AlogP: 0.43

#Rotatable Bonds: 2

Polar Surface Area: 68.53

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: -0.46

CX LogD: -0.46

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.79

Np Likeness Score: 1.34

References

1. Naylor MA, Jaffar M, Nolan J, Stephens MA, Butler S, Patel KB, Everett SA, Adams GE, Stratford IJ..  (1997)  2-Cyclopropylindoloquinones and their analogues as bioreductively activated antitumor agents: structure-activity in vitro and efficacy in vivo.,  40  (15): [PMID:9240349] [10.1021/jm9608422]

2. Naylor MA, Swann E, Everett SA, Jaffar M, Nolan J, Robertson N, Lockyer SD, Patel KB, Dennis MF, Stratford MR, Wardman P, Adams GE, Moody CJ, Stratford IJ..  (1998)  Indolequinone antitumor agents: reductive activation and elimination from (5-methoxy-1-methyl-4,7-dioxoindol-3-yl)methyl derivatives and hypoxia-selective cytotoxicity in vitro.,  41  (15): [PMID:9667963] [10.1021/jm970744w]

3. Swann E, Barraja P, Oberlander AM, Gardipee WT, Hudnott AR, Beall HD, Moody CJ..  (2001)  Indolequinone antitumor agents: correlation between quinone structure and rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase. Part 2.,  44  (20): [PMID:11563930] [10.1021/jm010884c]

4. Hernick M, Flader C, Borch RF..  (2002)  Design, synthesis, and biological evaluation of indolequinone phosphoramidate prodrugs targeted to DT-diaphorase.,  45  (16): [PMID:12139465] [10.1021/jm020191b]

5. Phillips RM, Naylor MA, Jaffar M, Doughty SW, Everett SA, Breen AG, Choudry GA, Stratford IJ..  (1999)  Bioreductive activation of a series of indolequinones by human DT-diaphorase: structure-activity relationships.,  42  (20): [PMID:10514277] [10.1021/jm991063z]

Source

Source(1):

• Scientific Literature