(C-c Ado)2-Amino-N-[9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-4-mercapto-butyramide

ID: ALA608049

PubChem CID: 46876000

Max Phase: Preclinical

Molecular Formula: C14H20N6O5S

Molecular Weight: 384.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(CCS)C(=O)Nc1ncnc2c1ncn2C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C14H20N6O5S/c15-6(1-2-26)13(24)19-11-8-12(17-4-16-11)20(5-18-8)14-10(23)9(22)7(3-21)25-14/h4-7,9-10,14,21-23,26H,1-3,15H2,(H,16,17,19,24)/t6?,7-,9-,10-,14?/m1/s1

Standard InChI Key:  JCBYGEMMCAGQEM-ICPFLIPISA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    6.5500   -4.1292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5500   -5.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0625   -3.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0625   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5500   -3.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -5.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8667   -3.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7875   -4.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6000   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6000   -2.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3250   -5.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -5.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6000   -4.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -3.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -3.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7750   -2.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -2.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5792   -6.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0000   -6.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500   -1.2792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7875   -2.2167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -4.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -4.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3625   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  2  0
  5  7  2  0
  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  4  1  0
 10  9  1  0
 11  6  1  0
 12  8  1  0
 13 10  1  0
 14  3  1  0
 15 16  1  0
 16 14  2  0
 17 13  2  0
 18 13  1  0
  6 19  1  6
 11 20  1  6
 21 18  1  0
 22 26  1  0
 12 23  1  1
 24 18  1  0
 25 23  1  0
 26 24  1  0
  4  5  1  0
 11 12  1  0
  9 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA608049

   2-amino-N-[9-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]-4-sulfanylbutanamide

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: 384.42

Molecular Weight (Monoisotopic): 384.1216

AlogP: -1.98

#Rotatable Bonds: 6

Polar Surface Area: 168.64

Molecular Species: NEUTRAL

HBA: 11

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.79

CX Basic pKa: 8.22

CX LogP: -2.26

CX LogD: -3.02

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.31

Np Likeness Score: 0.89

References

1. Patil SD, Schneller SW, Hosoya M, Snoeck R, Andrei G, Balzarini J, De Clercq E..  (1992)  Synthesis and antiviral properties of (+/-)-5'-noraristeromycin and related purine carbocyclic nucleosides. A new lead for anti-human cytomegalovirus agent design.,  35  (18): [PMID:1326633] [10.1021/jm00096a012]

Source

Source(1):

• Scientific Literature