3-(5'-Amino-5'-deoxyadenosine)-4-butylamino-cyclobut-3-ene-1,2-dione

ID: ALA3110199

Chembl Id: CHEMBL3110199

PubChem CID: 76310333

Max Phase: Preclinical

Molecular Formula: C18H23N7O5

Molecular Weight: 417.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCNc1c(NC[C@H]2O[C@@H](n3cnc4c(N)ncnc43)[C@H](O)[C@@H]2O)c(=O)c1=O

Standard InChI:  InChI=1S/C18H23N7O5/c1-2-3-4-20-9-10(14(28)13(9)27)21-5-8-12(26)15(29)18(30-8)25-7-24-11-16(19)22-6-23-17(11)25/h6-8,12,15,18,20-21,26,29H,2-5H2,1H3,(H2,19,22,23)/t8-,12-,15-,18-/m1/s1

Standard InChI Key:  IJRYROIEXPFMDF-OJJZPKOSSA-N

Alternative Forms

1. Parent:

   

   ALA3110199

   3-(5-Amino-5-deoxyadenosine)-4-(butylamino)cyclobut-3-ene-1,2-dione

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: 417.43

Molecular Weight (Monoisotopic): 417.1761

AlogP: -1.05

#Rotatable Bonds: 8

Polar Surface Area: 177.51

Molecular Species: NEUTRAL

HBA: 12

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.47

CX Basic pKa: 4.92

CX LogP: -0.89

CX LogD: -0.89

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.22

Np Likeness Score: 0.42

References

1. Moreau C, Kirchberger T, Swarbrick JM, Bartlett SJ, Fliegert R, Yorgan T, Bauche A, Harneit A, Guse AH, Potter BV..  (2013)  Structure-activity relationship of adenosine 5'-diphosphoribose at the transient receptor potential melastatin 2 (TRPM2) channel: rational design of antagonists.,  56  (24): [PMID:24304219] [10.1021/jm401497a]

2. Zhang Y, Jumppanen M, Maksimainen MM, Auno S, Awol Z, Ghemtio L, Venkannagari H, Lehtiö L, Yli-Kauhaluoma J, Xhaard H, Boije Af Gennäs G..  (2018)  Adenosine analogs bearing phosphate isosteres as human MDO1 ligands.,  26  (8): [PMID:29501416] [10.1016/j.bmc.2018.02.006]

Source

Source(1):

• Scientific Literature