ID: ALA126077

Max Phase: Preclinical

Molecular Formula: C16H11N3O2

Molecular Weight: 277.28

Molecule Type: Small molecule

Representations

Synonyms (5): Indirubin-3'-Monooxime | Indirubin-3'-Oxime | Indirubin-3-Monoxime | Indirubin-3-Oxime | Indirubin-3Monoxime
Synonyms from Alternative Forms(5):

Canonical SMILES:  O=Nc1c(-c2c(O)[nH]c3ccccc23)[nH]c2ccccc12

Standard InChI:  InChI=1S/C16H11N3O2/c20-16-13(9-5-1-3-7-11(9)18-16)15-14(19-21)10-6-2-4-8-12(10)17-15/h1-8,17-18,20H

Standard InChI Key:  FQCPPVRJPILDIK-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: 277.28

Molecular Weight (Monoisotopic): 277.0851

AlogP: 4.42

#Rotatable Bonds: 2

Polar Surface Area: 81.24

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.32

CX Basic pKa:

CX LogP: 3.60

CX LogD: 3.55

Aromatic Rings: 4

Heavy Atoms: 21

QED Weighted: 0.47

Np Likeness Score: 0.31

References

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4. Lee JW, Moon MJ, Min HY, Chung HJ, Park EJ, Park HJ, Hong JY, Kim YC, Lee SK..  (2005)  Induction of apoptosis by a novel indirubin-5-nitro-3'-monoxime, a CDK inhibitor, in human lung cancer cells.,  15  (17): [PMID:15993584] [10.1016/j.bmcl.2005.05.105]

5. Bhattacharjee AK, Geyer JA, Woodard CL, Kathcart AK, Nichols DA, Prigge ST, Li Z, Mott BT, Waters NC..  (2004)  A three-dimensional in silico pharmacophore model for inhibition of Plasmodium falciparum cyclin-dependent kinases and discovery of different classes of novel Pfmrk specific inhibitors.,  47  (22): [PMID:15481979] [10.1021/jm040108f]

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31. Gao Y, Davies SP, Augustin M, Woodward A, Patel UA, Kovelman R, Harvey KJ..  (2013)  A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.,  451  (2): [PMID:23398362] [10.1042/bj20121418]

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34. Yan L, Lai F, Chen X, Xiao Z..  (2015)  Discovery of novel indirubin-3'-monoxime derivatives as potent inhibitors against CDK2 and CDK9.,  25  (11): [PMID:25908517] [10.1016/j.bmcl.2015.03.066]

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Source

Source(2):

• Scientific Literature
• PubChem BioAssays