ID: ALA522503

Max Phase: Preclinical

Molecular Formula: C24H26BrN5O3

Molecular Weight: 512.41

Molecule Type: Small molecule

Representations

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

Standard InChI:  InChI=1S/C24H26BrN5O3/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)/b23-21-,28-22+

Standard InChI Key:  RPWRQYOHVXHGBO-YRZTTZRYSA-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. Pergola C, Gaboriaud-Kolar N, Jestädt N, König S, Kritsanida M, Schaible AM, Li H, Garscha U, Weinigel C, Barz D, Albring KF, Huber O, Skaltsounis AL, Werz O..  (2014)  Indirubin core structure of glycogen synthase kinase-3 inhibitors as novel chemotype for intervention with 5-lipoxygenase.,  57  (9): [PMID:24697244] [10.1021/jm401740w]

3. 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