ID: ALA3216892

Max Phase: Preclinical

Molecular Formula: C24H28BrCl2N5O3

Molecular Weight: 512.41

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cl.Cl.O=C1Nc2cc(Br)ccc2/C1=C1/Nc2ccccc2/C1=N\OCCN1CCN(CCO)CC1

Standard InChI:  InChI=1S/C24H26BrN5O3.2ClH/c25-16-5-6-17-20(15-16)27-24(32)21(17)23-22(18-3-1-2-4-19(18)26-23)28-33-14-12-30-9-7-29(8-10-30)11-13-31;;/h1-6,15,26,31H,7-14H2,(H,27,32);2*1H/b23-21-,28-22+;;

Standard InChI Key:  DLXPXTHNXDDQNS-GMWAXMIDSA-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: 512.41

Molecular Weight (Monoisotopic): 511.1219

AlogP: 2.57

#Rotatable Bonds: 6

Polar Surface Area: 89.43

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.61

CX Basic pKa: 7.49

CX LogP: 2.12

CX LogD: 1.77

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.31

Np Likeness Score: -0.30

References

1. Vougogiannopoulou K, Ferandin Y, Bettayeb K, Myrianthopoulos V, Lozach O, Fan Y, Johnson CH, Magiatis P, Skaltsounis AL, Mikros E, Meijer L..  (2008)  Soluble 3',6-substituted indirubins with enhanced selectivity toward glycogen synthase kinase -3 alter circadian period.,  51  (20): [PMID:18816110] [10.1021/jm800648y]

2. Gaboriaud-Kolar N, Myrianthopoulos V, Vougogiannopoulou K, Gerolymatos P, Horne DA, Jove R, Mikros E, Nam S, Skaltsounis AL..  (2016)  Natural-Based Indirubins Display Potent Cytotoxicity toward Wild-Type and T315I-Resistant Leukemia Cell Lines.,  79  (10): [PMID:27726390] [10.1021/acs.jnatprod.6b00285]

Source

Source(1):

• Scientific Literature