S-[5'-deoxy-5'[[(hydroxypyrophosphoroxy)phosphinyl]methyl]adenosyl-5']-L-homocysteine sulfoxide

ID: ALA1791417

PubChem CID: 56664653

Max Phase: Preclinical

Molecular Formula: C15H25N6O15P3S

Molecular Weight: 654.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](C(CP(=O)(O)OP(=O)(O)OP(=O)(O)O)[S+]([O-])CCC(N)C(=O)O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H25N6O15P3S/c16-6(15(24)25)1-2-40(33)7(3-37(26,27)35-39(31,32)36-38(28,29)30)11-9(22)10(23)14(34-11)21-5-20-8-12(17)18-4-19-13(8)21/h4-7,9-11,14,22-23H,1-3,16H2,(H,24,25)(H,26,27)(H,31,32)(H2,17,18,19)(H2,28,29,30)/t6?,7?,9-,10+,11+,14+,40?/m0/s1

Standard InChI Key:  MXSOOYSYSMMHNI-JLJGMEGWSA-N

Molfile:  

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M  CHG  2  18   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1791417

   2-amino-4-[1-[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]-2-[hydroxy-[hydroxy(phosphonooxy)phosphoryl]oxyphosphoryl]ethyl]sulfinylbutanoic 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: 654.38

Molecular Weight (Monoisotopic): 654.0311

AlogP: -2.64

#Rotatable Bonds: 13

Polar Surface Area: 356.28

Molecular Species: ZWITTERION

HBA: 16

HBD: 9

#RO5 Violations: 3

HBA (Lipinski): 21

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.07

CX Basic pKa: 9.11

CX LogP: -10.00

CX LogD: -15.13

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.08

Np Likeness Score: 1.09

References

1. Kappler F, Hai TT, Cotter RJ, Hyver KJ, Hampton A..  (1986)  Isozyme-specific enzyme inhibitors. 11. L-homocysteine-ATP S-C5' covalent adducts as inhibitors of rat methionine adenosyltransferases.,  29  (6): [PMID:3486976] [10.1021/jm00156a022]

Source

Source(1):

• Scientific Literature