9H-Purin-2-ylamine

ID: ALA388594

Cas Number: 452-06-2

PubChem CID: 9955

Product Number: A113172, Order Now?

Max Phase: Preclinical

Molecular Formula: C5H5N5

Molecular Weight: 135.13

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2-Aminopurine | 2-aminopurine|7H-purin-2-amine|452-06-2|9H-Purin-2-amine|1H-PURIN-2-AMINE|191236-69-8|Purine, 2-amino-|Aminopurine|Isoadenine|2-AP|SQ 22451|7H-Purin-2-amine (9CI)|2-amino purine|2'-amino-purine|7H-Purin-2-ylamine|9H-Purin-2-ylamine|SQ 22,451|CHEMBL388594|O14B3U97FW|CHEBI:479072|NSC24129|MFCD00005566|NSC-24129|SMR000857109|CCRIS 759|EINECS 207-197-4|NSC 24129|UNII-O14B3U97FW|Citronellylcinnamate|9H-Purin-2-amine #|BiomolKI_000044|AMINOPURINE, 2-|BiomolKI2_000050|7H-Purin-2-amine(9Show More⌵

Canonical SMILES:  Nc1nc2ncnc-2c[nH]1

Standard InChI:  InChI=1S/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10)

Standard InChI Key:  MWBWWFOAEOYUST-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 10 11  0  0  0  0  0  0  0  0999 V2000
    4.9304   -0.7425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4314   -0.5849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4314    0.7499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6449    0.4950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3594   -0.7425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2160   -0.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2160    0.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6449   -0.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9304    0.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9464    0.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0
  1  8  2  0
  2  6  2  0
  2 10  1  0
  3  7  1  0
  3 10  2  0
  4  8  1  0
  4  9  1  0
  5  8  1  0
  6  7  1  0
  7  9  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA388594

   2-Aminopurine

2. Alternative Forms:

   

   ALA388594

   2-Aminopurine nitrate

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: 135.13

Molecular Weight (Monoisotopic): 135.0545

AlogP: -0.11

#Rotatable Bonds: ┄

Polar Surface Area: 80.48

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.02

CX Basic pKa: ┄

CX LogP: -0.13

CX LogD: -1.25

Aromatic Rings: ┄

Heavy Atoms: 10

QED Weighted: 0.53

Np Likeness Score: -0.37

References

1. Young RC, Jones M, Milliner KJ, Rana KK, Ward JG..  (1990)  Purine derivatives as competitive inhibitors of human erythrocyte membrane phosphatidylinositol 4-kinase.,  33  (8): [PMID:2165159] [10.1021/jm00170a005]

2. Keough DT, Skinner-Adams T, Jones MK, Ng AL, Brereton IM, Guddat LW, de Jersey J..  (2006)  Lead compounds for antimalarial chemotherapy: purine base analogs discriminate between human and P. falciparum 6-oxopurine phosphoribosyltransferases.,  49  (25): [PMID:17149876] [10.1021/jm061012j]

3. Hsieh JF, Wu SH, Yang YL, Choong KF, Chen ST..  (2007)  The screening and characterization of 6-aminopurine-based xanthine oxidase inhibitors.,  15  (10): [PMID:17379526] [10.1016/j.bmc.2007.03.010]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. Cala O, Krimm I..  (2015)  Ligand-Orientation Based Fragment Selection in STD NMR Screening.,  58  (21): [PMID:26492576] [10.1021/acs.jmedchem.5b01114]

7. Chauhan V, Chaudhary D, Pathak U, Saxena N, Dhaked RK..  (2016)  In Silico Discovery and Validation of Amide Based Small Molecule Targeting the Enzymatic Site of Shiga Toxin.,  59  (23): [PMID:27933947] [10.1021/acs.jmedchem.6b01517]

8. Coxon CR, Anscombe E, Harnor SJ, Martin MP, Carbain B, Golding BT, Hardcastle IR, Harlow LK, Korolchuk S, Matheson CJ, Newell DR, Noble ME, Sivaprakasam M, Tudhope SJ, Turner DM, Wang LZ, Wedge SR, Wong C, Griffin RJ, Endicott JA, Cano C..  (2017)  Cyclin-Dependent Kinase (CDK) Inhibitors: Structure-Activity Relationships and Insights into the CDK-2 Selectivity of 6-Substituted 2-Arylaminopurines.,  60  (5): [PMID:28005359] [10.1021/acs.jmedchem.6b01254]

9. Goswami M, Wilke KE, Carlson EE..  (2017)  Rational Design of Selective Adenine-Based Scaffolds for Inactivation of Bacterial Histidine Kinases.,  60  (19): [PMID:28933546] [10.1021/acs.jmedchem.7b01066]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays