Adenosine 5'-triphosphate derivative

ID: ALA1791431

PubChem CID: 56668024

Max Phase: Preclinical

Molecular Formula: C13H22N5O13P3S

Molecular Weight: 581.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCSC(OP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C13H22N5O13P3S/c1-2-3-35-13(29-33(24,25)31-34(26,27)30-32(21,22)23)9-7(19)8(20)12(28-9)18-5-17-6-10(14)15-4-16-11(6)18/h4-5,7-9,12-13,19-20H,2-3H2,1H3,(H,24,25)(H,26,27)(H2,14,15,16)(H2,21,22,23)/t7-,8+,9-,12+,13?/m0/s1

Standard InChI Key:  UTGOGFHSHODTOS-XWUUDUPGSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
    9.4167   -3.9167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3458   -6.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2958   -5.5292    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.6333   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0083   -6.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6292   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9458   -5.5292    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.4083   -2.5875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0917   -7.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6792   -5.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8958   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1208   -5.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2667   -7.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4708   -5.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6458   -5.5250    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.5958   -5.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7708   -5.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167   -4.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2083   -2.8417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -4.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2083   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9417   -4.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -4.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -6.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5917   -4.7125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9417   -6.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5958   -7.7375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -6.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8208   -5.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7542   -7.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167   -1.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8708   -4.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8708   -3.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1583   -3.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3 12  1  0
  4  1  1  0
  5 10  1  0
  6  4  2  0
  7 17  1  0
  8 11  2  0
  9  2  1  0
 10  2  1  0
 11  1  1  0
 12  7  1  0
 13  9  1  0
 14  3  1  0
 15 14  1  0
  5 16  1  1
 17 16  1  0
 18  6  1  0
 19  4  1  0
 20 22  1  0
 21  3  2  0
 22 19  2  0
 23  7  2  0
 24 15  2  0
 25  3  1  0
 26 16  1  0
 27  7  1  0
  9 28  1  6
 29 15  1  0
 30 15  1  0
 13 31  1  6
 32 18  1  0
 33 26  1  0
 34 33  1  0
 35 34  1  0
  8  6  1  0
  5 13  1  0
 18 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1791431

   [[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]-propylsulfanylmethoxy]-hydroxyphosphoryl] 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: 581.33

Molecular Weight (Monoisotopic): 581.0148

AlogP: -0.16

#Rotatable Bonds: 11

Polar Surface Area: 279.13

Molecular Species: ACID

HBA: 15

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.89

CX Basic pKa: 4.92

CX LogP: -3.61

CX LogD: -8.70

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.13

Np Likeness Score: 0.88

References

1. Kappler F, Hai TT, Hampton A..  (1986)  Isozyme-specific enzyme inhibitors. 10. Adenosine 5'-triphosphate derivatives as substrates or inhibitors of methionine adenosyltransferases of rat normal and hepatoma tissues.,  29  (3): [PMID:3950912] [10.1021/jm00153a003]

Source

Source(1):

• Scientific Literature