ID: ALA3216893

Max Phase: Preclinical

Molecular Formula: C26H32BrCl2N5O4

Molecular Weight: 556.46

Molecule Type: Small molecule

Representations

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

Standard InChI:  InChI=1S/C26H30BrN5O4.2ClH/c27-18-5-6-19-22(17-18)29-26(34)23(19)25-24(20-3-1-2-4-21(20)28-25)30-36-15-12-32-9-7-31(8-10-32)11-14-35-16-13-33;;/h1-6,17,28,33H,7-16H2,(H,29,34);2*1H/b25-23-,30-24+;;

Standard InChI Key:  QKKQNWWTERHAMS-RXGHSYFKSA-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: 556.46

Molecular Weight (Monoisotopic): 555.1481

AlogP: 2.59

#Rotatable Bonds: 9

Polar Surface Area: 98.66

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.61

CX Basic pKa: 7.33

CX LogP: 2.07

CX LogD: 1.80

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.25

Np Likeness Score: -0.29

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