N6-[4-[2-[3,4,5-Trimethoxybenzamido]ethyl]benzyl]adenosine-5'-N-methylcarboxamide

ID: ALA1095000

PubChem CID: 46887672

Max Phase: Preclinical

Molecular Formula: C29H33N7O8

Molecular Weight: 607.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)[C@H]1O[C@@H](n2cnc3c(NCc4ccc(CNC(=O)c5cc(OC)c(OC)c(OC)c5)cc4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C29H33N7O8/c1-30-28(40)24-21(37)22(38)29(44-24)36-14-35-20-25(33-13-34-26(20)36)31-11-15-5-7-16(8-6-15)12-32-27(39)17-9-18(41-2)23(43-4)19(10-17)42-3/h5-10,13-14,21-22,24,29,37-38H,11-12H2,1-4H3,(H,30,40)(H,32,39)(H,31,33,34)/t21-,22+,24-,29+/m0/s1

Standard InChI Key:  GOASSFPKZZNPIH-UKNKTOQLSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1095000

   (2S,3S,4R,5R)-3,4-dihydroxy-N-methyl-5-[6-[[4-[[(3,4,5-trimethoxybenzoyl)amino]methyl]phenyl]methylamino]purin-9-yl]oxolane-2-carboxamide

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: 607.62

Molecular Weight (Monoisotopic): 607.2391

AlogP: 0.76

#Rotatable Bonds: 11

Polar Surface Area: 191.21

Molecular Species: NEUTRAL

HBA: 13

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.39

CX Basic pKa: 4.69

CX LogP: 0.00

CX LogD: 0.00

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.16

Np Likeness Score: -0.13

References

1. Devine SM, Gregg A, Figler H, McIntosh K, Urmaliya V, Linden J, Pouton CW, White PJ, Bottle SE, Scammells PJ..  (2010)  Synthesis and evaluation of new N6-substituted adenosine-5'-N-methylcarboxamides as A3 adenosine receptor agonists.,  18  (9): [PMID:20385496] [10.1016/j.bmc.2010.03.047]

Source

Source(1):

• Scientific Literature