(2S,3R,4R,5S,6R)-2-(5-(chroman-6-ylmethyl)-2-hydroxy-4-methoxyphenyl)-5-fluoro-6-(hydroxymethyl)-5-methyltetrahydro-2H-pyran-3,4-diol

ID: ALA4752364

PubChem CID: 162652542

Max Phase: Preclinical

Molecular Formula: C24H29FO7

Molecular Weight: 448.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(O)c([C@@H]2O[C@H](CO)[C@@](C)(F)[C@H](O)[C@H]2O)cc1Cc1ccc2c(c1)CCCO2

Standard InChI:  InChI=1S/C24H29FO7/c1-24(25)20(12-26)32-22(21(28)23(24)29)16-10-15(19(30-2)11-17(16)27)9-13-5-6-18-14(8-13)4-3-7-31-18/h5-6,8,10-11,20-23,26-29H,3-4,7,9,12H2,1-2H3/t20-,21+,22+,23-,24-/m1/s1

Standard InChI Key:  SUDLIXRHTBWUAX-OYTPZHDJSA-N

Molfile:  

 
     RDKit          2D

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   27.0379   -4.6667    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.4587   -3.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6292   -3.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   28.8911   -3.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8911   -3.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1749   -2.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6069   -2.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1749   -5.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7389   -2.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6051   -4.3678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7365   -1.8813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3167   -3.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0319   -2.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0348   -1.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.6043   -1.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7450   -3.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4608   -2.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1698   -3.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1703   -1.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4578   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8884   -1.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8837   -2.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5894   -3.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3043   -2.7368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3090   -1.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5987   -1.4975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7499   -1.4818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7512   -0.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8889   -1.4798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  2  1  0
  4  8  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  1
  5 10  1  1
  4 11  1  1
  6 12  1  6
 11 13  1  0
  9 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  9  1  0
 15 19  1  0
 19 20  1  0
 20 21  2  0
 21 25  1  0
 24 22  1  0
 22 23  2  0
 23 20  1  0
 24 25  2  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 16 30  1  0
 30 31  1  0
 18 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4752364

   ---

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: 448.49

Molecular Weight (Monoisotopic): 448.1897

AlogP: 2.20

#Rotatable Bonds: 5

Polar Surface Area: 108.61

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.24

CX Basic pKa: ┄

CX LogP: 2.34

CX LogD: 2.34

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.56

Np Likeness Score: 1.10

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