5-(6-Amino-purin-9-yl)-cyclopent-3-ene-1,2-diol

ID: ALA299961

Chembl Id: CHEMBL299961

PubChem CID: 490351

Max Phase: Preclinical

Molecular Formula: C10H11N5O2

Molecular Weight: 233.23

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H11N5O2/c11-9-7-10(13-3-12-9)15(4-14-7)5-1-2-6(16)8(5)17/h1-6,8,16-17H,(H2,11,12,13)/t5-,6-,8+/m1/s1

Standard InChI Key:  RQPALADHFYHEHK-JKMUOGBPSA-N

Alternative Forms

1. Parent:

   

   ALA299961

   DHCeA

Molecule Features

Natural Product: Yes

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: 233.23

Molecular Weight (Monoisotopic): 233.0913

AlogP: -0.76

#Rotatable Bonds: 1

Polar Surface Area: 110.08

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.19

CX Basic pKa: 4.10

CX LogP: -1.15

CX LogD: -1.15

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.56

Np Likeness Score: 0.82

References

1. Wolfe MS, Lee Y, Bartlett WJ, Borcherding DR, Borchardt RT..  (1992)  4'-modified analogues of aristeromycin and neplanocin A: synthesis and inhibitory activity toward S-adenosyl-L-homocysteine hydrolase.,  35  (10): [PMID:1588558] [10.1021/jm00088a013]

2. Kim HO, Yoo SJ, Ahn HS, Choi WJ, Moon HR, Lee KM, Chun MW, Jeong LS..  (2004)  Synthesis of fluorinated cyclopentenyladenine as potent inhibitor of S-adenosylhomocysteine hydrolase.,  14  (9): [PMID:15080985] [10.1016/j.bmcl.2004.02.039]

3. Sufrin JR, Spiess AJ, Kramer DL, Libby PR, Miller JT, Bernacki RJ, Lee YH, Borchardt RT, Porter CW..  (1991)  Targeting 5'-deoxy-5'-(methylthio)adenosine phosphorylase by 5'-haloalkyl analogues of 5'-deoxy-5'-(methylthio)adenosine.,  34  (8): [PMID:1908523] [10.1021/jm00112a039]

4. Obara T, Shuto S, Saito Y, Snoeck R, Andrei G, Balzarini J, De Clercq E, Matsuda A..  (1996)  New neplanocin analogues. 7. Synthesis and antiviral activity of 2-halo derivatives of neplanocin A.,  39  (19): [PMID:8809173] [10.1021/jm960145+]

5. Narayanan SR, Keller BT, Borcherding DR, Scholtz SA, Borchardt RT..  (1988)  9-(trans-2',trans-3'-dihydroxycyclopent-4'-enyl) derivatives of adenine and 3-deazaadenine: potent inhibitors of bovine liver S-adenosylhomocysteine hydrolase.,  31  (3): [PMID:3346868] [10.1021/jm00398a002]

6. Cai S, Li QS, Borchardt RT, Kuczera K, Schowen RL..  (2007)  The antiviral drug ribavirin is a selective inhibitor of S-adenosyl-L-homocysteine hydrolase from Trypanosoma cruzi.,  15  (23): [PMID:17845853] [10.1016/j.bmc.2007.08.029]

7. Lee KM, Choi WJ, Lee Y, Lee HJ, Zhao LX, Lee HW, Park JG, Kim HO, Hwang KY, Heo YS, Choi S, Jeong LS..  (2011)  X-ray crystal structure and binding mode analysis of human S-adenosylhomocysteine hydrolase complexed with novel mechanism-based inhibitors, haloneplanocin A analogues.,  54  (4): [PMID:21226494] [10.1021/jm1010836]

8. Converso A, Hartingh T, Fraley ME, Garbaccio RM, Hartman GD, Huang SY, Majercak JM, McCampbell A, Na SJ, Ray WJ, Savage MJ, Wolffe C, Yeh S, Yu Y, White R, Zhang R..  (2014)  Adenosine analogue inhibitors of S-adenosylhomocysteine hydrolase.,  24  (12): [PMID:24813734] [10.1016/j.bmcl.2014.04.034]

Source

Source(1):

• Scientific Literature