ID: ALA493656

Max Phase: Preclinical

Molecular Formula: C25H28BrN5O3

Molecular Weight: 526.44

Molecule Type: Small molecule

Representations

Canonical SMILES:  COCCN1CCN(CCO/N=C2C(=C3/C(=O)Nc4cc(Br)ccc43)/Nc3ccccc3/2)CC1

Standard InChI:  InChI=1S/C25H28BrN5O3/c1-33-14-12-30-8-10-31(11-9-30)13-15-34-29-23-19-4-2-3-5-20(19)27-24(23)22-18-7-6-17(26)16-21(18)28-25(22)32/h2-7,16,27H,8-15H2,1H3,(H,28,32)/b24-22-,29-23+

Standard InChI Key:  HUDVRTTVWXVPMO-HLDOLBPXSA-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: 526.44

Molecular Weight (Monoisotopic): 525.1376

AlogP: 3.22

#Rotatable Bonds: 7

Polar Surface Area: 78.43

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.61

CX Basic pKa: 7.54

CX LogP: 2.76

CX LogD: 2.38

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.33

Np Likeness Score: -0.42

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