ID: ALA1090058

Max Phase: Preclinical

Molecular Formula: C22H26O6

Molecular Weight: 386.44

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc(Cc2cc([C@@H]3OC4(COC4)[C@@H](O)[C@H](O)[C@H]3O)ccc2C)cc1

Standard InChI:  InChI=1S/C22H26O6/c1-13-3-6-15(10-16(13)9-14-4-7-17(26-2)8-5-14)20-18(23)19(24)21(25)22(28-20)11-27-12-22/h3-8,10,18-21,23-25H,9,11-12H2,1-2H3/t18-,19-,20+,21+/m1/s1

Standard InChI Key:  DTAFHPYHXXDOPB-CGXNFDGLSA-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: 386.44

Molecular Weight (Monoisotopic): 386.1729

AlogP: 1.52

#Rotatable Bonds: 4

Polar Surface Area: 88.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.48

CX Basic pKa:

CX LogP: 2.06

CX LogD: 2.06

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.74

Np Likeness Score: 0.87

References

1. Robinson RP, Mascitti V, Boustany-Kari CM, Carr CL, Foley PM, Kimoto E, Leininger MT, Lowe A, Klenotic MK, Macdonald JI, Maguire RJ, Masterson VM, Maurer TS, Miao Z, Patel JD, Préville C, Reese MR, She L, Steppan CM, Thuma BA, Zhu T..  (2010)  C-Aryl glycoside inhibitors of SGLT2: Exploration of sugar modifications including C-5 spirocyclization.,  20  (5): [PMID:20149653] [10.1016/j.bmcl.2010.01.075]

2. Mascitti V, Maurer TS, Robinson RP, Bian J, Boustany-Kari CM, Brandt T, Collman BM, Kalgutkar AS, Klenotic MK, Leininger MT, Lowe A, Maguire RJ, Masterson VM, Miao Z, Mukaiyama E, Patel JD, Pettersen JC, Préville C, Samas B, She L, Sobol Z, Steppan CM, Stevens BD, Thuma BA, Tugnait M, Zeng D, Zhu T..  (2011)  Discovery of a clinical candidate from the structurally unique dioxa-bicyclo[3.2.1]octane class of sodium-dependent glucose cotransporter 2 inhibitors.,  54  (8): [PMID:21449606] [10.1021/jm200049r]

3. Orozco CC, Atkinson K, Ryu S, Chang G, Keefer C, Lin J, Riccardi K, Mongillo RK, Tess D, Filipski KJ, Kalgutkar AS, Litchfield J, Scott D, Di L..  (2020)  Structural attributes influencing unbound tissue distribution.,  185  [PMID:31732255] [10.1016/j.ejmech.2019.111813]

Source

Source(1):

• Scientific Literature