2-Amino-4-{1-[5-(6-amino-1,6-dihydro-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-ethylsulfanyl}-butyric acid diphosphonic phosphoramidic acid

ID: ALA1791411

PubChem CID: 56674982

Max Phase: Preclinical

Molecular Formula: C15H28N7O13P3S

Molecular Weight: 639.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(CCSC(CP(=O)(O)OP(=O)(O)NP(=O)(O)O)[C@H]1O[C@@H](n2cnc3c2NC=NC3N)[C@H](O)[C@@H]1O)C(=O)O

Standard InChI:  InChI=1S/C15H28N7O13P3S/c16-6(15(25)26)1-2-39-7(3-36(27,28)35-38(32,33)21-37(29,30)31)11-9(23)10(24)14(34-11)22-5-20-8-12(17)18-4-19-13(8)22/h4-7,9-12,14,23-24H,1-3,16-17H2,(H,18,19)(H,25,26)(H,27,28)(H4,21,29,30,31,32,33)/t6?,7?,9-,10+,11+,12?,14+/m0/s1

Standard InChI Key:  YLVZRTXDQLHSMJ-PIBUWKRVSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA1791411

   2-amino-4-[1-[(2S,3S,4R,5R)-5-(6-amino-3,6-dihydropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]-2-[hydroxy-[hydroxy-(phosphonoamino)phosphoryl]oxyphosphoryl]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: 639.41

Molecular Weight (Monoisotopic): 639.0679

AlogP: -2.20

#Rotatable Bonds: 13

Polar Surface Area: 334.63

Molecular Species: ZWITTERION

HBA: 15

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.79

CX Basic pKa: 9.50

CX LogP: -10.61

CX LogD: -16.15

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.10

Np Likeness Score: 0.87

References

1. Kappler F, Vrudhula VM, Hampton A..  (1987)  Isozyme-specific enzyme inhibitors. 14. 5'(R)-C-[(L-homocystein-S-yl)methyl]adenosine 5'-(beta,gamma-imidotriphosphate), a potent inhibitor of rat methionine adenosyltransferases.,  30  (9): [PMID:3498043] [10.1021/jm00392a013]

Source

Source(1):

• Scientific Literature