5'-Methoxy-1H,1'H-[2,3']biindolylidene-3,2'-dione 3-{O-[2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-oxime}

ID: ALA1165371

Chembl Id: CHEMBL1165371

PubChem CID: 136016378

Max Phase: Preclinical

Molecular Formula: C25H27N3O9

Molecular Weight: 513.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)/C(=C1/Nc3ccccc3/C1=N\OCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)N2

Standard InChI:  InChI=1S/C25H27N3O9/c1-34-12-6-7-16-14(10-12)18(24(33)27-16)20-19(13-4-2-3-5-15(13)26-20)28-36-9-8-35-25-23(32)22(31)21(30)17(11-29)37-25/h2-7,10,17,21-23,25-26,29-32H,8-9,11H2,1H3,(H,27,33)/b20-18-,28-19+/t17-,21-,22+,23-,25-/m1/s1

Standard InChI Key:  OXFMTURCMJXJOI-XKKHQZTASA-N

Alternative Forms

1. Parent:

   

   ALA1165371

   ---

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: 513.50

Molecular Weight (Monoisotopic): 513.1747

AlogP: 0.02

#Rotatable Bonds: 7

Polar Surface Area: 171.33

Molecular Species: NEUTRAL

HBA: 11

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 10.71

CX Basic pKa: 3.95

CX LogP: -0.45

CX LogD: -0.45

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.17

Np Likeness Score: 0.82

References

1. Cheng X, Rasqué P, Vatter S, Merz KH, Eisenbrand G..  (2010)  Synthesis and cytotoxicity of novel indirubin-5-carboxamides.,  18  (12): [PMID:20488718] [10.1016/j.bmc.2010.04.066]

2. Wang H, Wang Z, Wei C, Wang J, Xu Y, Bai G, Yao Q, Zhang L, Chen Y..  (2021)  Anticancer potential of indirubins in medicinal chemistry: Biological activity, structural modification, and structure-activity relationship.,  223  [PMID:34161865] [10.1016/j.ejmech.2021.113652]

Source

Source(1):

• Scientific Literature