(2S,3R,4R,5S,6R)-2-(5-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)-2,4-dimethoxyphenyl)-5-fluoro-6-(hydroxymethyl)-5-methyltetrahydro-2H-pyran-3,4-diol

ID: ALA4753488

PubChem CID: 162653958

Max Phase: Preclinical

Molecular Formula: C24H29FO8

Molecular Weight: 464.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c([C@@H]2O[C@H](CO)[C@@](C)(F)[C@H](O)[C@H]2O)cc1Cc1ccc2c(c1)OCCO2

Standard InChI:  InChI=1S/C24H29FO8/c1-24(25)20(12-26)33-22(21(27)23(24)28)15-10-14(17(29-2)11-18(15)30-3)8-13-4-5-16-19(9-13)32-7-6-31-16/h4-5,9-11,20-23,26-28H,6-8,12H2,1-3H3/t20-,21+,22+,23-,24-/m1/s1

Standard InChI Key:  WSASRWODVRTLFZ-OYTPZHDJSA-N

Molfile:  

 
     RDKit          2D

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    9.9749   -2.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4000   -1.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9801   -1.5382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9784   -0.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9 14  2  0
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 18 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4753488

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 464.49

Molecular Weight (Monoisotopic): 464.1846

AlogP: 1.95

#Rotatable Bonds: 6

Polar Surface Area: 106.84

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.46

CX Basic pKa: ┄

CX LogP: 1.68

CX LogD: 1.68

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.60

Np Likeness Score: 0.81

References

1. Xu G,Du F,Kuo GH,Xu JZ,Liang Y,Demarest K,Gaul MD.  (2020)  5,5-Difluoro- and 5-Fluoro-5-methyl-hexose-based C-Glucosides as potent and orally bioavailable SGLT1 and SGLT2 dual inhibitors.,  30  (17): [PMID:32738984] [10.1016/j.bmcl.2020.127387]

Source

Source(1):

• Scientific Literature