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

ID: ALA609066

Chembl Id: CHEMBL609066

PubChem CID: 46876972

Max Phase: Preclinical

Molecular Formula: C12H15N3O6

Molecular Weight: 297.27

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H15N3O6/c13-11(20)8-6(2-1-3-16)15(5-14-8)12-10(19)9(18)7(4-17)21-12/h5,7,9-10,12,16-19H,3-4H2,(H2,13,20)/t7-,9-,10-,12?/m1/s1

Standard InChI Key:  QIKBJRGAWGHCIN-IYYKZFDCSA-N

Alternative Forms

1. Parent:

   

   ALA609066

   1-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(3-hydroxyprop-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: 297.27

Molecular Weight (Monoisotopic): 297.0961

AlogP: -3.06

#Rotatable Bonds: 3

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: 12.40

CX Basic pKa: 3.04

CX LogP: -2.84

CX LogD: -2.84

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.37

Np Likeness Score: 0.97

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