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

ID: ALA609078

PubChem CID: 46877039

Max Phase: Preclinical

Molecular Formula: C15H26N7O14P3S

Molecular Weight: 653.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2C1O[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?/m0/s1

Standard InChI Key:  CISDHKHIEKDPHJ-SJAFKOQPSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA609078

   2-amino-4-[(1S)-1-[(2S,3S,4R)-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. 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