(2R,3R,5R)-2-Hydroxymethyl-5-{6-[(R)-(tetrahydro-furan-3-yl)amino]-purin-9-yl}-tetrahydro-furan-3,4-diol

ID: ALA392149

Chembl Id: CHEMBL392149

Max Phase: Phase

Molecular Formula: C14H19N5O5

Molecular Weight: 337.34

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Tecadenoson | CVT-510

Canonical SMILES:  OC[C@H]1O[C@@H](n2cnc3c(N[C@@H]4CCOC4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C14H19N5O5/c20-3-8-10(21)11(22)14(24-8)19-6-17-9-12(15-5-16-13(9)19)18-7-1-2-23-4-7/h5-8,10-11,14,20-22H,1-4H2,(H,15,16,18)/t7-,8-,10-,11-,14-/m1/s1

Standard InChI Key:  OESBDSFYJMDRJY-BAYCTPFLSA-N

Alternative Forms

1. Parent:

   

   ALA392149

   TECADENOSON

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 337.34

Molecular Weight (Monoisotopic): 337.1386

AlogP: -1.36

#Rotatable Bonds: 4

Polar Surface Area: 134.78

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 4.68

CX LogP: -1.89

CX LogD: -1.89

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.53

Np Likeness Score: 0.86

References

1. Morrison CF, Elzein E, Jiang B, Ibrahim PN, Marquart T, Palle V, Shenk KD, Varkhedkar V, Maa T, Wu L, Wu Y, Zeng D, Fong I, Lustig D, Leung K, Zablocki JA..  (2004)  Structure-affinity relationships of 5'-aromatic ethers and 5'-aromatic sulfides as partial A1 adenosine agonists, potential supraventricular anti-arrhythmic agents.,  14  (14): [PMID:15203164] [10.1016/j.bmcl.2004.04.096]

2. Palle VP, Varkhedkar V, Ibrahim P, Ahmed H, Li Z, Gao Z, Ozeck M, Wu Y, Zeng D, Wu L, Leung K, Chu N, Zablocki JA..  (2004)  Affinity and intrinsic efficacy (IE) of 5'-carbamoyl adenosine analogues for the A1 adenosine receptor--efforts towards the discovery of a chronic ventricular rate control agent for the treatment of atrial fibrillation (AF).,  14  (2): [PMID:14698198] [10.1016/j.bmcl.2003.09.094]

3. Ashton TD, Aumann KM, Baker SP, Schiesser CH, Scammells PJ..  (2007)  Structure-activity relationships of adenosines with heterocyclic N6-substituents.,  17  (24): [PMID:17967536] [10.1016/j.bmcl.2007.10.028]

4. Cappellacci L, Franchetti P, Vita P, Petrelli R, Lavecchia A, Costa B, Spinetti F, Martini C, Klotz KN, Grifantini M..  (2008)  5'-Carbamoyl derivatives of 2'-C-methyl-purine nucleosides as selective A1 adenosine receptor agonists: affinity, efficacy, and selectivity for A1 receptor from different species.,  16  (1): [PMID:17933541] [10.1016/j.bmc.2007.09.035]

5. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

6. Lepist EI, Damaraju VL, Zhang J, Gati WP, Yao SY, Smith KM, Karpinski E, Young JD, Leung KH, Cass CE..  (2013)  Transport of A1 adenosine receptor agonist tecadenoson by human and mouse nucleoside transporters: evidence for blood-brain barrier transport by murine equilibrative nucleoside transporter 1 mENT1.,  41  (4): [PMID:23388705] [10.1124/dmd.112.049858]

7. Lepist EI, Damaraju VL, Zhang J, Gati WP, Yao SY, Smith KM, Karpinski E, Young JD, Leung KH, Cass CE..  (2013)  Transport of A1 adenosine receptor agonist tecadenoson by human and mouse nucleoside transporters: evidence for blood-brain barrier transport by murine equilibrative nucleoside transporter 1 mENT1.,  41  (4): [PMID:23388705] [10.1124/dmd.112.049858]

8. Unpublished dataset, 

9. Yu J, Mannes P, Jung YH, Ciancetta A, Bitant A, Lieberman DI, Khaznadar S, Auchampach JA, Gao ZG, Jacobson KA..  (2018)  Structure activity relationship of 2-arylalkynyl-adenine derivatives as human A₃ adenosine receptor antagonists.,  9  (11): [PMID:30568760] [10.1039/C8MD00317C]

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names