1-(3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-(4-hydroxy-but-1-ynyl)-1H-imidazole-4-carboxylic acid amide

ID: ALA608782

Chembl Id: CHEMBL608782

PubChem CID: 46876997

Max Phase: Preclinical

Molecular Formula: C13H17N3O6

Molecular Weight: 311.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1ncn(C2O[C@H](CO)[C@@H](O)[C@H]2O)c1C#CCCO

Standard InChI:  InChI=1S/C13H17N3O6/c14-12(21)9-7(3-1-2-4-17)16(6-15-9)13-11(20)10(19)8(5-18)22-13/h6,8,10-11,13,17-20H,2,4-5H2,(H2,14,21)/t8-,10-,11-,13?/m1/s1

Standard InChI Key:  ZMKBZMLYCRACQW-LXGADPQPSA-N

Alternative Forms

1. Parent:

   

   ALA608782

   1-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(4-hydroxybut-1-ynyl)imidazole-4-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: 311.29

Molecular Weight (Monoisotopic): 311.1117

AlogP: -2.67

#Rotatable Bonds: 4

Polar Surface Area: 151.06

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.41

CX Basic pKa: 3.08

CX LogP: -2.55

CX LogD: -2.55

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.38

Np Likeness Score: 0.86

References

1. Minakawa N, Takeda T, Sasaki T, Matsuda A, Ueda T..  (1991)  Nucleosides and nucleotides. 96. Synthesis and antitumor activity of 5-ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide (EICAR) and its derivatives.,  34  (2): [PMID:1995901] [10.1021/jm00106a045]

Source

Source(1):

• Scientific Literature