[2-amino-4-{3-[5-(6-amino-9H-9-purinyl)-3,4-dihydroxytetrahydro-2-furanyl]-3-hydroxypropylsulfanyl}butanoic acid]phosphonoamidodiphosphoric acid

ID: ALA3706404

PubChem CID: 122197258

Max Phase: Preclinical

Molecular Formula: C16H28N7O14P3S

Molecular Weight: 667.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H]([C@@H](CCSCCC(N)C(=O)O)OP(=O)(O)OP(=O)(O)NP(=O)(O)O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C16H28N7O14P3S/c17-7(16(26)27)1-3-41-4-2-8(36-40(33,34)37-39(31,32)22-38(28,29)30)12-10(24)11(25)15(35-12)23-6-21-9-13(18)19-5-20-14(9)23/h5-8,10-12,15,24-25H,1-4,17H2,(H,26,27)(H,33,34)(H2,18,19,20)(H4,22,28,29,30,31,32)/t7?,8-,10+,11-,12-,15-/m1/s1

Standard InChI Key:  YSQBQFZXWAVDTE-GIWIQNKBSA-N

Molfile:  

     RDKit          2D

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    1.4507   -1.8882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8404   -2.7901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2357   -2.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0188   -1.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1609   -1.5526    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5898   -1.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4464   -1.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8754   -1.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7402   -2.3765    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  3 13  1  0
  4  1  1  0
  5  4  2  0
  6 11  2  0
  7  2  1  0
  8 19  1  0
  9  2  1  0
 10  3  1  0
 11  1  1  0
 12  9  1  0
 13  8  1  0
 14  7  1  0
 15 10  1  0
 12 16  1  0
 17  5  1  0
 18  4  1  0
 16 19  1  6
 20 23  1  0
 21 30  1  0
 22  3  2  0
 23 18  2  0
 24  8  2  0
 25 15  2  0
 26  3  1  0
 27 21  2  0
 28  8  1  0
  7 29  1  1
 30 39  1  0
 31 15  1  0
 32 15  1  0
 14 33  1  1
 34 17  1  0
 35 16  1  0
 36 21  1  0
 37 30  1  0
 38 40  1  0
 39 41  1  0
 40 35  1  0
 41 38  1  0
  5  6  1  0
 14 12  1  0
 20 17  2  0
 12 42  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3706404

   ---

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: 667.42

Molecular Weight (Monoisotopic): 667.0628

AlogP: -1.76

#Rotatable Bonds: 15

Polar Surface Area: 345.25

Molecular Species: ZWITTERION

HBA: 16

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 21

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.32

CX Basic pKa: 9.50

CX LogP: -7.68

CX LogD: -14.92

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.07

Np Likeness Score: 0.87

References

1. Vrudhula VM, Kappler F, Afshar C, Ginell SL, Lessinger L, Hampton A..  (1989)  Approaches to isozyme-specific inhibitors. 16. A novel methyl-C5' covalent adduct of L-ethionine and beta,gamma-imido-ATP as a potent multisubstrate inhibitor of rat methionine adenosyltransferases.,  32  (4): [PMID:2784835] [10.1021/jm00124a026]

Source

Source(1):

• Scientific Literature