2-Amino-8-mercapto-1,9-dihydro-purin-6-one

ID: ALA178006

Chembl Id: CHEMBL178006

Cas Number: 6324-72-7

PubChem CID: 135423614

Product Number: A133535

Max Phase: Preclinical

Molecular Formula: C5H5N5OS

Molecular Weight: 183.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2[nH]c(S)nc2c(=O)[nH]1

Standard InChI:  InChI=1S/C5H5N5OS/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H5,6,7,8,9,10,11,12)

Standard InChI Key:  JHEKNTQSGTVPAO-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA178006

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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: 183.20

Molecular Weight (Monoisotopic): 183.0215

AlogP: -0.48

#Rotatable Bonds: ┄

Polar Surface Area: 100.45

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.22

CX Basic pKa: ┄

CX LogP: -0.37

CX LogD: -0.85

Aromatic Rings: 2

Heavy Atoms: 12

QED Weighted: 0.41

Np Likeness Score: -0.57

References

1. Miller DJ, Ravikumar K, Shen H, Suh JK, Kerwin SM, Robertus JD..  (2002)  Structure-based design and characterization of novel platforms for ricin and shiga toxin inhibition.,  45  (1): [PMID:11754581] [10.1021/jm010186s]

2. Hevener KE, Yun MK, Qi J, Kerr ID, Babaoglu K, Hurdle JG, Balakrishna K, White SW, Lee RE..  (2010)  Structural studies of pterin-based inhibitors of dihydropteroate synthase.,  53  (1): [PMID:19899766] [10.1021/jm900861d]

3. PubChem BioAssay data set, 

4. Yun MK, Hoagland D, Kumar G, Waddell MB, Rock CO, Lee RE, White SW..  (2014)  The identification, analysis and structure-based development of novel inhibitors of 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase.,  22  (7): [PMID:24613625] [10.1016/j.bmc.2014.02.022]

5. Dennis ML, Chhabra S, Wang ZC, Debono A, Dolezal O, Newman J, Pitcher NP, Rahmani R, Cleary B, Barlow N, Hattarki M, Graham B, Peat TS, Baell JB, Swarbrick JD..  (2014)  Structure-based design and development of functionalized Mercaptoguanine derivatives as inhibitors of the folate biosynthesis pathway enzyme 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase from Staphylococcus aureus.,  57  (22): [PMID:25357262] [10.1021/jm501417f]

6. Dennis ML, Pitcher NP, Lee MD, DeBono AJ, Wang ZC, Harjani JR, Rahmani R, Cleary B, Peat TS, Baell JB, Swarbrick JD..  (2016)  Structural Basis for the Selective Binding of Inhibitors to 6-Hydroxymethyl-7,8-dihydropterin Pyrophosphokinase from Staphylococcus aureus and Escherichia coli.,  59  (11): [PMID:27094768] [10.1021/acs.jmedchem.6b00002]

7.  (2012)  Heterocyclic GTP Cyclohydrolase 1 Inhibitors For the Treatment of Pain, 

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• Patent Bioactivity Data