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

ID: ALA129014

Chembl Id: CHEMBL129014

Cas Number: 150132-22-2

PubChem CID: 126704

Max Phase: Preclinical

Molecular Formula: C10H13N5O3

Molecular Weight: 251.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Noraristeromycin | noraristeromycin|(1S,2R,3S,4R)-4-(6-aminopurin-9-yl)cyclopentane-1,2,3-triol|142635-42-5|CHEMBL129014|4-(6-amino-9H-purin-9-yl)cyclopentane-1,2,3-triol|5'-Noraristeromycin|(-)-5 inverted exclamation marka-Noraristeromycin|(1S,2R,3S,4R)-4-(6-amino-9H-purin-9-yl)cyclopentane-1,2,3-triol|4-(6-Amino-9H-purin-9-yl)-1,2,3-cyclopentanetriol|(-)-5'-Noraristeromycin|(+/-)-5'-Noraristeromycin|SCHEMBL1231088|DTXSID40931561|BDBM50135288|(+-)-(1alpha,2beta,3beta,4alpha)-4-(6-Amino-9H-purinShow More⌵

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-/m1/s1

Standard InChI Key:  VFKHECGAEJNAMV-HETMPLHPSA-N

Alternative Forms

1. Parent:

   

   ALA129014

   NORARISTEROMYCIN

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, Chen X, Rao J, Schneller SW, Ikeda S, Snoeck R, Andrei G, Balzarini J, De Clercq E..  (1995)  3-deaza- and 7-deaza-5'-noraristeromycin and their antiviral properties.,  38  (6): [PMID:7699695] [10.1021/jm00006a023]

2. 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]

3. 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]

4. 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]

5. Kitade Y, Kojima H, Zulfiqur F, Kim HS, Wataya Y..  (2003)  Synthesis of 2-fluoronoraristeromycin and its inhibitory activity against Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase.,  13  (22): [PMID:14592485] [10.1016/j.bmcl.2003.08.074]

6. 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]

7. Ando T, Iwata M, Zulfiqar F, Miyamoto T, Nakanishi M, Kitade Y..  (2008)  Synthesis of 2-modified aristeromycins and their analogs as potent inhibitors against Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase.,  16  (7): [PMID:18295495] [10.1016/j.bmc.2008.01.046]

8. Ando T, Kojima K, Chahota P, Kozaki A, Milind ND, Kitade Y..  (2008)  Synthesis of 4'-modified noraristeromycins to clarify the effect of the 4'-hydroxyl groups for inhibitory activity against S-adenosyl-L-homocysteine hydrolase.,  18  (8): [PMID:18374570] [10.1016/j.bmcl.2008.03.029]

9. Kim BG, Chun TG, Lee HY, Snapper ML..  (2009)  A new structural class of S-adenosylhomocysteine hydrolase inhibitors.,  17  (18): [PMID:19692248] [10.1016/j.bmc.2009.07.061]

Source

Source(1):

• Scientific Literature