(2S,3R,4R,5S,6R)-2-[4-chloro-3-[[4-[(3R)-tetrahydrofuran-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

ID: ALA4521016

Cas Number: 864070-43-9

PubChem CID: 11949687

Max Phase: Preclinical

Molecular Formula: C23H27ClO7

Molecular Weight: 450.92

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](c2ccc(Cl)c(Cc3ccc(O[C@@H]4CCOC4)cc3)c2)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C23H27ClO7/c24-18-6-3-14(23-22(28)21(27)20(26)19(11-25)31-23)10-15(18)9-13-1-4-16(5-2-13)30-17-7-8-29-12-17/h1-6,10,17,19-23,25-28H,7-9,11-12H2/t17-,19-,20-,21+,22-,23+/m1/s1

Standard InChI Key:  OBWASQILIWPZMG-VUOLKEHKSA-N

Molfile:  

 
     RDKit          2D

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   21.1592  -14.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1592  -15.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.7000  -13.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4097  -12.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1181  -13.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1203  -14.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4121  -14.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8261  -12.7994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5342  -13.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2808  -12.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8325  -13.4850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4209  -14.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6234  -14.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9916  -12.7966    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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 26 25  1  1
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 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 26  1  0
  3 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4521016

   (2S,3R,4R,5S,6R)-2-(4-Chloro-3-(4-(((R)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Molecule Features

Natural Product: Yes

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: 450.92

Molecular Weight (Monoisotopic): 450.1445

AlogP: 1.61

#Rotatable Bonds: 6

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: 12.57

CX Basic pKa: ┄

CX LogP: 1.66

CX LogD: 1.66

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: 0.89

References

1. Haider K, Pathak A, Rohilla A, Haider MR, Ahmad K, Yar MS..  (2019)  Synthetic strategy and SAR studies of C-glucoside heteroaryls as SGLT2 inhibitor: A review.,  184  [PMID:31630053] [10.1016/j.ejmech.2019.111773]

Source

Source(1):

• Scientific Literature