ID: ALA3216218

Max Phase: Preclinical

Molecular Formula: C23H26BrCl2N5O2

Molecular Weight: 482.38

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN1CCN(CCO/N=C2C(=C3/C(=O)Nc4cc(Br)ccc43)/Nc3ccccc3/2)CC1.Cl.Cl

Standard InChI:  InChI=1S/C23H24BrN5O2.2ClH/c1-28-8-10-29(11-9-28)12-13-31-27-21-17-4-2-3-5-18(17)25-22(21)20-16-7-6-15(24)14-19(16)26-23(20)30;;/h2-7,14,25H,8-13H2,1H3,(H,26,30);2*1H/b22-20-,27-21+;;

Standard InChI Key:  VCIMOUDBIZQNAS-YADBPHKCSA-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: 482.38

Molecular Weight (Monoisotopic): 481.1113

AlogP: 3.21

#Rotatable Bonds: 4

Polar Surface Area: 69.20

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.61

CX Basic pKa: 7.68

CX LogP: 2.81

CX LogD: 2.34

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: -0.45

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