3-(4-Cyclopropylphenylmethyl)-1-(beta-D-glucopyranosyl)-4-methylindole

ID: ALA3109016

Chembl Id: CHEMBL3109016

PubChem CID: 67196949

Max Phase: Preclinical

Molecular Formula: C25H29NO5

Molecular Weight: 423.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc2c1c(Cc1ccc(C3CC3)cc1)cn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C25H29NO5/c1-14-3-2-4-19-21(14)18(11-15-5-7-16(8-6-15)17-9-10-17)12-26(19)25-24(30)23(29)22(28)20(13-27)31-25/h2-8,12,17,20,22-25,27-30H,9-11,13H2,1H3/t20-,22-,23+,24-,25-/m1/s1

Standard InChI Key:  PGWYHQLQLNCJMZ-PRDVQWLOSA-N

Alternative Forms

1. Parent:

   

   ALA3109016

   (2R,3R,4S,5S,6R)-2-[3-[(4-cyclopropylphenyl)methyl]-4-methylindol-1-yl]-6-(hydroxymethyl)oxane-3,4,5-triol

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: 423.51

Molecular Weight (Monoisotopic): 423.2046

AlogP: 2.39

#Rotatable Bonds: 5

Polar Surface Area: 95.08

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.36

CX Basic pKa: ┄

CX LogP: 3.27

CX LogD: 3.27

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.51

Np Likeness Score: 0.76

References

1. Nomura S, Yamamoto Y, Matsumura Y, Ohba K, Sakamaki S, Kimata H, Nakayama K, Kuriyama C, Matsushita Y, Ueta K, Tsuda-Tsukimoto M..  (2014)  Novel Indole-N-glucoside, TA-1887 As a Sodium Glucose Cotransporter 2 Inhibitor for Treatment of Type 2 Diabetes.,  5  (1): [PMID:24900773] [10.1021/ml400339b]

Source

Source(1):

• Scientific Literature