ID: ALA193692

Max Phase: Preclinical

Molecular Formula: C24H25N5O4

Molecular Weight: 447.50

Molecule Type: Small molecule

Representations

Synonyms (1): MRS-3310
Synonyms from Alternative Forms(1):

Canonical SMILES:  OC[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C24H25N5O4/c30-12-18-20(31)21(32)24(33-18)29-14-28-19-22(26-13-27-23(19)29)25-11-17(15-7-3-1-4-8-15)16-9-5-2-6-10-16/h1-10,13-14,17-18,20-21,24,30-32H,11-12H2,(H,25,26,27)/t18-,20-,21-,24-/m1/s1

Standard InChI Key:  TUGMXIURLRAWSS-UMCMBGNQSA-N

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

Properties

Molecular Weight: 447.50

Molecular Weight (Monoisotopic): 447.1907

AlogP: 1.68

#Rotatable Bonds: 7

Polar Surface Area: 125.55

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.45

CX Basic pKa: 3.75

CX LogP: 1.72

CX LogD: 1.72

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.34

Np Likeness Score: 0.45

References

1. Bridges AJ, Bruns RF, Ortwine DF, Priebe SR, Szotek DL, Trivedi BK..  (1988)  N6-[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]adenosine and its uronamide derivatives. Novel adenosine agonists with both high affinity and high selectivity for the adenosine A2 receptor.,  31  (7): [PMID:3385722] [10.1021/jm00402a004]

2. Trivedi BK, Bruns RF..  (1989)  C2,N6-disubstituted adenosines: synthesis and structure-activity relationships.,  32  (8): [PMID:2754691] [10.1021/jm00128a002]

3. Bridges AJ, Moos WH, Szotek DL, Trivedi BK, Bristol JA, Heffner TG, Bruns RF, Downs DA..  (1987)  N6-(2,2-diphenylethyl)adenosine, a novel adenosine receptor agonist with antipsychotic-like activity.,  30  (10): [PMID:2888894] [10.1021/jm00393a003]

4. Trivedi BK, Bristol JA, Bruns RF, Haleen SJ, Steffen RP..  (1988)  N6-(arylalkyl)adenosines. Identification of N6-(9-fluorenylmethyl)adenosine as a highly potent agonist for the adenosine A2 receptor.,  31  (1): [PMID:3336027] [10.1021/jm00396a044]

5. Bressi JC, Choe J, Hough MT, Buckner FS, Van Voorhis WC, Verlinde CL, Hol WG, Gelb MH..  (2000)  Adenosine analogues as inhibitors of Trypanosoma brucei phosphoglycerate kinase: elucidation of a novel binding mode for a 2-amino-N(6)-substituted adenosine.,  43  (22): [PMID:11063610] [10.1021/jm000287a]

6. Jacobson KA, van Galen PJ, Williams M..  (1992)  Adenosine receptors: pharmacology, structure-activity relationships, and therapeutic potential.,  35  (3): [PMID:1738138] [10.1021/jm00081a001]

7. Kusachi S, Thompson RD, Yamada N, Daly DT, Olsson RA..  (1986)  Dog coronary artery adenosine receptor: structure of the N6-aryl subregion.,  29  (6): [PMID:3012086] [10.1021/jm00156a016]

8. Tchilibon S, Joshi BV, Kim SK, Duong HT, Gao ZG, Jacobson KA..  (2005)  (N)-methanocarba 2,N6-disubstituted adenine nucleosides as highly potent and selective A3 adenosine receptor agonists.,  48  (6): [PMID:15771421] [10.1021/jm049580r]

9. Deflorian F, Kumar TS, Phan K, Gao ZG, Xu F, Wu H, Katritch V, Stevens RC, Jacobson KA..  (2012)  Evaluation of molecular modeling of agonist binding in light of the crystallographic structure of an agonist-bound A₂A adenosine receptor.,  55  (1): [PMID:22104008] [10.1021/jm201461q]

10. Baraldi PG, Preti D, Borea PA, Varani K..  (2012)  Medicinal chemistry of A₃ adenosine receptor modulators: pharmacological activities and therapeutic implications.,  55  (12): [PMID:22468757] [10.1021/jm300087j]

11. Tosh DK,Brackett CM,Jung YH,Gao ZG,Banerjee M,Blagg BSJ,Jacobson KA.  (2021)  Biological Evaluation of 5'-(N-Ethylcarboxamido)adenosine Analogues as Grp94-Selective Inhibitors.,  12  (3): [PMID:33738064] [10.1021/acsmedchemlett.0c00509]

Source

Source(1):

• Scientific Literature