8-(2-Chloro-3,4,5-trimethoxy-benzyl)-9-pent-4-ynyl-9H-purin-6-ylamine

ID: ALA326523

Chembl Id: CHEMBL326523

PubChem CID: 448971

Max Phase: Preclinical

Molecular Formula: C20H22ClN5O3

Molecular Weight: 415.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCCCn1c(Cc2cc(OC)c(OC)c(OC)c2Cl)nc2c(N)ncnc21

Standard InChI:  InChI=1S/C20H22ClN5O3/c1-5-6-7-8-26-14(25-16-19(22)23-11-24-20(16)26)10-12-9-13(27-2)17(28-3)18(29-4)15(12)21/h1,9,11H,6-8,10H2,2-4H3,(H2,22,23,24)

Standard InChI Key:  WUJFGZAAFADPSF-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA326523

   8-(2-Chloro-3,4,5-trimethoxy-benzyl)-9-pent-4-ylnyl-9H-purin-6-ylamine

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: 415.88

Molecular Weight (Monoisotopic): 415.1411

AlogP: 3.09

#Rotatable Bonds: 8

Polar Surface Area: 97.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.70

CX LogP: 2.74

CX LogD: 2.74

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: -0.47

References

1. Dymock B, Barril X, Beswick M, Collier A, Davies N, Drysdale M, Fink A, Fromont C, Hubbard RE, Massey A, Surgenor A, Wright L..  (2004)  Adenine derived inhibitors of the molecular chaperone HSP90-SAR explained through multiple X-ray structures.,  14  (2): [PMID:14698151] [10.1016/j.bmcl.2003.11.011]

2. Rodina A, Vilenchik M, Moulick K, Aguirre J, Kim J, Chiang A, Litz J, Clement CC, Kang Y, She Y, Wu N, Felts S, Wipf P, Massague J, Jiang X, Brodsky JL, Krystal GW, Chiosis G..  (2007)  Selective compounds define Hsp90 as a major inhibitor of apoptosis in small-cell lung cancer.,  3  (8): [PMID:17603540] [10.1038/nchembio.2007.10]

Source

Source(1):

• Scientific Literature