ID: ALA3216659

Max Phase: Preclinical

Molecular Formula: C22H24BrCl2N5O2

Molecular Weight: 468.36

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cl.Cl.O=C1Nc2cc(Br)ccc2/C1=C1/Nc2ccccc2/C1=N\OCCN1CCNCC1

Standard InChI:  InChI=1S/C22H22BrN5O2.2ClH/c23-14-5-6-15-18(13-14)26-22(29)19(15)21-20(16-3-1-2-4-17(16)25-21)27-30-12-11-28-9-7-24-8-10-28;;/h1-6,13,24-25H,7-12H2,(H,26,29);2*1H/b21-19-,27-20+;;

Standard InChI Key:  CVZJSHRSJMHZLV-BEDCTKBTSA-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: 468.36

Molecular Weight (Monoisotopic): 467.0957

AlogP: 2.86

#Rotatable Bonds: 4

Polar Surface Area: 77.99

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.63

CX Basic pKa: 9.20

CX LogP: 2.27

CX LogD: 0.62

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.37

Np Likeness Score: -0.35

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]

3. Wang H, Wang Z, Wei C, Wang J, Xu Y, Bai G, Yao Q, Zhang L, Chen Y..  (2021)  Anticancer potential of indirubins in medicinal chemistry: Biological activity, structural modification, and structure-activity relationship.,  223  [PMID:34161865] [10.1016/j.ejmech.2021.113652]

Source

Source(1):

• Scientific Literature