(2R,3R,4S,5S,6R)-2-(3-(4-cyclopropylbenzyl)-4-fluoro-1H-indol-1-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

ID: ALA1782369

Chembl Id: CHEMBL1782369

Cas Number: 1003005-29-5

PubChem CID: 24759836

Max Phase: Preclinical

Molecular Formula: C24H26FNO5

Molecular Weight: 427.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](n2cc(Cc3ccc(C4CC4)cc3)c3c(F)cccc32)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C24H26FNO5/c25-17-2-1-3-18-20(17)16(10-13-4-6-14(7-5-13)15-8-9-15)11-26(18)24-23(30)22(29)21(28)19(12-27)31-24/h1-7,11,15,19,21-24,27-30H,8-10,12H2/t19-,21-,22+,23-,24-/m1/s1

Standard InChI Key:  PXRGAWZIQZMHTH-PFKOEMKTSA-N

Alternative Forms

1. Parent:

   

   ALA1782369

   3-(4-Cyclopropylbenzyl)-4-fluoroindole-N-glucoside

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: 427.47

Molecular Weight (Monoisotopic): 427.1795

AlogP: 2.22

#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: 2.90

CX LogD: 2.90

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.50

Np Likeness Score: 0.53

References

1. Wu JS, Peng YH, Wu JM, Hsieh CJ, Wu SH, Coumar MS, Song JS, Lee JC, Tsai CH, Chen CT, Liu YW, Chao YS, Wu SY..  (2010)  Discovery of non-glycoside sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors by ligand-based virtual screening.,  53  (24): [PMID:21090651] [10.1021/jm101080v]

2. 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