2-Amino-4-{2-[5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-3-phosphonoaminoHydroxyphosphinoy-loxy-phosphonic acid-ethylsulfanyl}-butyric acid

ID: ALA1791426

PubChem CID: 56638667

Max Phase: Preclinical

Molecular Formula: C15H26N7O14P3S

Molecular Weight: 653.40

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H26N7O14P3S/c16-6(15(25)26)1-2-40-7(3-21-37(27,28)35-39(32,33)36-38(29,30)31)11-9(23)10(24)14(34-11)22-5-20-8-12(17)18-4-19-13(8)22/h4-7,9-11,14,23-24H,1-3,16H2,(H,25,26)(H,32,33)(H2,17,18,19)(H2,21,27,28)(H2,29,30,31)/t6?,7-,9+,10-,11-,14-/m1/s1

Standard InChI Key:  CISDHKHIEKDPHJ-UDYRUIFHSA-N

Molfile:  

     RDKit          2D

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    4.1381   -2.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917   -1.8648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9543   -4.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1738   -4.1175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4438   -2.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2600   -4.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2600   -8.2380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8311   -9.0630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2600   -7.4130    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.5064   -5.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8311   -9.8880    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.3844   -1.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1331   -7.9360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8032   -3.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9745   -6.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4350   -7.4130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8311  -10.7130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9581   -9.3650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5469   -4.1130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1339   -4.7467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0850   -7.4130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0061   -9.8880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6561   -9.8880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3348   -6.0805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6890   -4.9380    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2982   -1.0443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2613   -5.3505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8324   -6.1755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1179   -4.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4035   -5.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2600   -5.7630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9519   -4.4887    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  3 11  1  0
  4  1  1  0
  5  4  2  0
  6  9  2  0
  7  2  1  0
  8  2  1  0
  9  1  1  0
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 15 12  1  0
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 17  4  1  0
 18 23  1  0
 10 19  1  0
 20 24  1  0
 21 30  1  0
 22  3  2  0
 23 17  2  0
 24 19  1  0
 25 13  2  0
 26 15  2  0
 27  3  1  0
 28 21  2  0
  7 29  1  1
 30 39  1  0
 31 13  1  0
 32 15  1  0
 33 15  1  0
 14 34  1  1
 35 19  1  0
 36 16  1  0
 37 21  1  0
 38 30  1  0
 39 40  1  0
 40 35  1  0
 19 41  1  1
  6  5  1  0
 14 10  1  0
 16 18  2  0
 10 42  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1791426

   2-amino-4-[(1R)-1-[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]-2-[[hydroxy-[hydroxy(phosphonooxy)phosphoryl]oxyphosphoryl]amino]ethyl]sulfanylbutanoic acid

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: 653.40

Molecular Weight (Monoisotopic): 653.0471

AlogP: -2.15

#Rotatable Bonds: 14

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: 1.05

CX Basic pKa: 9.50

CX LogP: -8.52

CX LogD: -13.85

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.10

Np Likeness Score: 1.09

References

1. Kappler F, Vrudhula VM, Hampton A..  (1988)  Toward the synthesis of isozyme-specific enzyme inhibitors. Potent inhibitors of rat methionine adenosyltransferases. Effect of one-atom elongation of the ribose-P alpha bridge in two covalent adducts of L-methionine and beta,gamma-imido-ATP.,  31  (2): [PMID:3257524] [10.1021/jm00397a020]

2. Vrudhula VM, Kappler F, Hampton A..  (1987)  Isozyme-specific enzyme inhibitors. 13. S-[5'(R)-[(N-triphosphoamino)methyl]adenosyl]-L-homocysteine, a potent inhibitor of rat methionine adenosyltransferases.,  30  (5): [PMID:3572977] [10.1021/jm00388a024]

Source

Source(1):

• Scientific Literature