4-(6-Amino-purin-9-yl)-cyclopentane-1,2,3-triol

ID: ALA2051948

PubChem CID: 490429

Max Phase: Preclinical

Molecular Formula: C10H13N5O3

Molecular Weight: 251.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@H]1C[C@@H](O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C10H13N5O3/c11-9-6-10(13-2-12-9)15(3-14-6)4-1-5(16)8(18)7(4)17/h2-5,7-8,16-18H,1H2,(H2,11,12,13)/t4-,5+,7+,8-/m0/s1

Standard InChI Key:  VFKHECGAEJNAMV-LAHCRNKXSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
    5.3387   -2.6527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1340   -2.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1382   -1.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1888   -3.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3512   -1.3160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8597   -1.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3137   -4.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3725   -3.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5849   -4.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8503   -1.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8503   -2.8151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0019   -4.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5624   -1.5783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5624   -2.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9008   -4.8639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8586   -0.3415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4600   -5.4886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1857   -4.2268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  1  6
  5  6  2  0
  6  1  1  0
  7  4  1  0
  8  4  1  0
  9  7  1  0
 10  3  2  0
 11  2  2  0
 12  8  1  0
 13 14  2  0
 14 11  1  0
  7 15  1  1
 16 10  1  0
  9 17  1  1
 12 18  1  6
  5  3  1  0
  9 12  1  0
 13 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2051948

   (1R,2S,3R,4S)-4-(6-aminopurin-9-yl)cyclopentane-1,2,3-triol

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: 251.25

Molecular Weight (Monoisotopic): 251.1018

AlogP: -1.56

#Rotatable Bonds: 1

Polar Surface Area: 130.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.95

CX Basic pKa: 3.69

CX LogP: -2.25

CX LogD: -2.25

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.48

Np Likeness Score: 0.93

References

1. Siddiqi SM, Jacobson KA, Esker JL, Olah ME, Ji XD, Melman N, Tiwari KN, Secrist JA, Schneller SW, Cristalli G..  (1995)  Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors.,  38  (7): [PMID:7707320] [10.1021/jm00007a014]

2. Seley KL, Schneller SW, Korba B..  (1998)  Does the anti-hepatitis B virus activity of (+)-5'-noraristeromycin exist in its 4'-epimer and 4'-deoxygenated derivatives?,  41  (12): [PMID:9622558] [10.1021/jm980038a]

3. Siddiqi SM, Chen X, Schneller SW, Ikeda S, Snoeck R, Andrei G, Balzarini J, De Clercq E..  (1994)  Antiviral enantiomeric preference for 5'-noraristeromycin.,  37  (4): [PMID:8120872] [10.1021/jm00030a014]

Source

Source(1):

• Scientific Literature