6-N-cyclopropyl-9-(6,6-dibromo-5,6-dideoxy-beta-D-ribo-hex-5-enofuranosyl)adenine

ID: ALA381146

Chembl Id: CHEMBL381146

PubChem CID: 11691156

Max Phase: Preclinical

Molecular Formula: C14H15Br2N5O3

Molecular Weight: 461.11

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O[C@@H]1[C@H](O)[C@@H](C=C(Br)Br)O[C@H]1n1cnc2c(NC3CC3)ncnc21

Standard InChI:  InChI=1S/C14H15Br2N5O3/c15-8(16)3-7-10(22)11(23)14(24-7)21-5-19-9-12(20-6-1-2-6)17-4-18-13(9)21/h3-7,10-11,14,22-23H,1-2H2,(H,17,18,20)/t7-,10-,11-,14-/m1/s1

Standard InChI Key:  SWMINOMAZCPOIW-FRJWGUMJSA-N

Alternative Forms

1. Parent:

   

   ALA381146

   (2R,3R,4S,5R)-2-[6-(cyclopropylamino)purin-9-yl]-5-(2,2-dibromoethenyl)oxolane-3,4-diol

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: 461.11

Molecular Weight (Monoisotopic): 458.9542

AlogP: 1.65

#Rotatable Bonds: 4

Polar Surface Area: 105.32

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 3.73

CX LogP: 1.15

CX LogD: 1.15

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.64

Np Likeness Score: 0.39

References

1. Rapp M, Haubrich TA, Perrault J, Mackey ZB, McKerrow JH, Chiang PK, Wnuk SF..  (2006)  Antitrypanosomal activity of 5'-deoxy-5'-(iodomethylene)adenosine and related 6-N-cyclopropyladenosine analogues.,  49  (6): [PMID:16539398] [10.1021/jm0511379]

2. Dornbush PJ, Vazquez-Anaya G, Shokar A, Benson S, Rapp M, Wnuk SF, Wrischnik LA, Land KM..  (2010)  AdoHcy hydrolase of Trichomonas vaginalis: studies of the effects of 5'-modified adenosine analogues and related 6-N-cyclopropyl derivatives.,  20  (24): [PMID:21044841] [10.1016/j.bmcl.2010.10.014]

Source

Source(1):

• Scientific Literature