3-(5'-Ammonium-5'-deoxyadenosine)-4-[(3-hydroxyphenyl)amino]cyclobut-3-ene-1,2-dione

ID: ALA4225209

Chembl Id: CHEMBL4225209

PubChem CID: 145970332

Max Phase: Preclinical

Molecular Formula: C20H19N7O6

Molecular Weight: 453.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](CNc2c(Nc3cccc(O)c3)c(=O)c2=O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C20H19N7O6/c21-18-13-19(24-6-23-18)27(7-25-13)20-17(32)14(29)10(33-20)5-22-11-12(16(31)15(11)30)26-8-2-1-3-9(28)4-8/h1-4,6-7,10,14,17,20,22,26,28-29,32H,5H2,(H2,21,23,24)/t10-,14-,17-,20-/m1/s1

Standard InChI Key:  UVINJGIQFWWQKJ-DRIBAISHSA-N

Alternative Forms

1. Parent:

   

   ALA4225209

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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: 453.42

Molecular Weight (Monoisotopic): 453.1397

AlogP: -0.82

#Rotatable Bonds: 6

Polar Surface Area: 197.74

Molecular Species: NEUTRAL

HBA: 13

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.29

CX Basic pKa: 4.92

CX LogP: -0.88

CX LogD: -0.89

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.20

Np Likeness Score: 0.38

References

1. 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