N'-beta-L-Rhamnopyranosylindirubin

ID: ALA498148

Chembl Id: CHEMBL498148

PubChem CID: 135857533

Max Phase: Preclinical

Molecular Formula: C22H20N2O6

Molecular Weight: 408.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1O[C@H](N2C(=O)/C(=C3\Nc4ccccc4C3=O)c3ccccc32)[C@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C22H20N2O6/c1-10-17(25)19(27)20(28)22(30-10)24-14-9-5-3-7-12(14)15(21(24)29)16-18(26)11-6-2-4-8-13(11)23-16/h2-10,17,19-20,22-23,25,27-28H,1H3/b16-15-/t10-,17-,19+,20+,22-/m0/s1

Standard InChI Key:  AVXRSJWDLOZVBS-ZUYNXGORSA-N

Alternative Forms

1. Parent:

   

   ALA498148

   ---

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

Calculated Properties

Molecular Weight: 408.41

Molecular Weight (Monoisotopic): 408.1321

AlogP: 0.88

#Rotatable Bonds: 1

Polar Surface Area: 119.33

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.12

CX Basic pKa: ┄

CX LogP: 0.93

CX LogD: 0.93

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.52

Np Likeness Score: 0.95

References

1. Libnow S, Methling K, Hein M, Michalik D, Harms M, Wende K, Flemming A, Köckerling M, Reinke H, Bednarski PJ, Lalk M, Langer P..  (2008)  Synthesis of indirubin-N'-glycosides and their anti-proliferative activity against human cancer cell lines.,  16  (10): [PMID:18434163] [10.1016/j.bmc.2008.04.003]

2. 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