2,4:3,5-dibenzylidene-D-xylosediethyl dithioacetal

ID: ALA456199

PubChem CID: 44588352

Max Phase: Preclinical

Molecular Formula: C23H28O4S2

Molecular Weight: 432.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCSC(SCC)[C@@H]1O[C@H](c2ccccc2)O[C@@H]2CO[C@H](c3ccccc3)O[C@@H]21

Standard InChI:  InChI=1S/C23H28O4S2/c1-3-28-23(29-4-2)20-19-18(25-22(27-20)17-13-9-6-10-14-17)15-24-21(26-19)16-11-7-5-8-12-16/h5-14,18-23H,3-4,15H2,1-2H3/t18-,19+,20-,21+,22-/m1/s1

Standard InChI Key:  LDBUJIGWHJRDNE-OQEHDIDLSA-N

Molfile:  

     RDKit          2D

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    7.1853   -3.6114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8980   -4.0177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8980   -2.3675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8980   -1.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1829   -1.1277    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0433   -1.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3236   -2.3724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7530   -2.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4621   -2.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1788   -2.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1836   -1.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4657   -1.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7560   -1.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6033   -1.9570    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5992   -4.4323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0
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  2 12  1  1
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 20 21  1  0
 21 22  1  0
 22 23  1  0
 10 11  1  0
  4  5  1  1
 24 25  2  0
  1  2  1  0
 25 26  1  0
 12 13  2  0
 26 27  2  0
  5  6  1  0
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 13 14  1  0
 28 29  2  0
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 22 24  1  1
  1  4  1  0
 18 30  1  6
 14 15  2  0
 19 31  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA456199

   (2R,4R,4aS,6S,8aR)-4-[bis(ethylsulfanyl)methyl]-2,6-diphenyl-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxine

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: 432.61

Molecular Weight (Monoisotopic): 432.1429

AlogP: 5.42

#Rotatable Bonds: 7

Polar Surface Area: 36.92

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.18

CX LogD: 6.18

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.54

Np Likeness Score: 0.30

References

1. Gruzman A, Shamni O, Ben Yakir M, Sandovski D, Elgart A, Alpert E, Cohen G, Hoffman A, Katzhendler Y, Cerasi E, Sasson S..  (2008)  Novel D-xylose derivatives stimulate muscle glucose uptake by activating AMP-activated protein kinase alpha.,  51  (24): [PMID:19049348] [10.1021/jm8008713]

Source

Source(1):

• Scientific Literature