2-hexylthio-ATP-alpha-S

ID: ALA598853

PubChem CID: 46228456

Max Phase: Preclinical

Molecular Formula: C16H28N5O12P3S2

Molecular Weight: 639.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCSc1nc(N)c2ncn([C@H]3O[C@@H](COP(O)(=S)OP(=O)(O)OP(=O)(O)O)[C@H](O)[C@@H]3O)c2n1

Standard InChI:  InChI=1S/C16H28N5O12P3S2/c1-2-3-4-5-6-38-16-19-13(17)10-14(20-16)21(8-18-10)15-12(23)11(22)9(31-15)7-30-36(29,37)33-35(27,28)32-34(24,25)26/h8-9,11-12,15,22-23H,2-7H2,1H3,(H,27,28)(H,29,37)(H2,17,19,20)(H2,24,25,26)/t9-,11-,12-,15-,36?/m0/s1

Standard InChI Key:  ZVZNYNIFYBLKFQ-PJPBMIAMSA-N

Molfile:  

     RDKit          2D

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    4.0048  -13.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8333  -12.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5478  -12.4958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1609  -13.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9678  -12.8763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3034  -12.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1239  -12.2088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5809  -13.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2954  -13.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0099  -13.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5809  -14.2533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7243  -13.0158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2954  -15.4908    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2374  -12.8714    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4300  -13.3564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1837  -13.0208    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9374  -12.6852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223  -13.5389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8482  -12.2671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7243  -15.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4388  -15.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1533  -15.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8678  -15.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5822  -15.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  5  6  1  6
  6  7  1  0
  7  8  2  0
  8 10  1  0
  9  6  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 11 15  1  0
 13 16  1  0
 16 17  1  0
  1 18  1  1
  2 19  1  1
  3 20  1  6
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 24 28  2  0
 26 29  2  0
 22 30  2  0
 22 31  1  0
 24 32  1  0
 26 33  1  0
 17 34  1  0
  1  2  1  0
 34 35  1  0
  2  3  1  0
 35 36  1  0
  3  4  1  0
 36 37  1  0
  4  5  1  0
 37 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA598853

   [[(2S,3R,4S,5S)-5-(6-amino-2-hexylsulfanylpurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphinothioyl] phosphono hydrogen phosphate

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: 639.48

Molecular Weight (Monoisotopic): 639.0389

AlogP: 1.16

#Rotatable Bonds: 14

Polar Surface Area: 262.06

Molecular Species: ACID

HBA: 15

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.06

CX Basic pKa: 5.12

CX LogP: -1.00

CX LogD: -6.17

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.07

Np Likeness Score: 0.54

References

1. Eliahu S, Barr HM, Camden J, Weisman GA, Fischer B..  (2010)  A novel insulin secretagogue based on a dinucleoside polyphosphate scaffold.,  53  (6): [PMID:20175517] [10.1021/jm901621h]

Source

Source(1):

• Scientific Literature