2-Methyl-6-oxo-4-[(pyridin-3-ylmethyl)-amino]-1,6-dihydro-pyrimidine-5-carbonitrile

ID: ALA17125

Chembl Id: CHEMBL17125

PubChem CID: 135413516

Max Phase: Unknown

Molecular Formula: C12H11N5O

Molecular Weight: 241.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms from Alternative Forms(4): Pelrinone hcl | Pelrinone hydrochloride | AY-28,768 | AY-28768

Canonical SMILES:  Cc1nc(=O)c(C#N)c(NCc2cccnc2)[nH]1

Standard InChI:  InChI=1S/C12H11N5O/c1-8-16-11(10(5-13)12(18)17-8)15-7-9-3-2-4-14-6-9/h2-4,6H,7H2,1H3,(H2,15,16,17,18)

Standard InChI Key:  NZXHFDXOCVIYLO-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA17125

   PELRINONE

2. Alternative Forms:

   

   ALA17125

   PELRINONE HYDROCHLORIDE

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 241.25

Molecular Weight (Monoisotopic): 241.0964

AlogP: 0.96

#Rotatable Bonds: 3

Polar Surface Area: 94.46

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.51

CX Basic pKa: 3.82

CX LogP: -0.60

CX LogD: -0.63

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.83

Np Likeness Score: -1.73

References

1. Erhardt PW, Hagedorn AA, Davey D, Pease CA, Venepalli BR, Griffin CW, Gomez RP, Wiggins JR, Ingebretsen WR, Pang D..  (1989)  Cardiotonic agents. 5. Fragments from the heterocycle-phenyl-imidazole pharmacophore.,  32  (6): [PMID:2542552] [10.1021/jm00126a005]

2. Hagedorn AA, Erhardt PW, Lumma WC, Wohl RA, Cantor E, Chou YL, Ingebretsen WR, Lampe JW, Pang D, Pease CA..  (1987)  Cardiotonic agents. 2. (Imidazolyl)aroylimidazolones, highly potent and selective positive inotropic agents.,  30  (8): [PMID:3039132] [10.1021/jm00391a013]

3. Erhardt PW..  (1987)  In search of the digitalis replacement.,  30  (2): [PMID:3027335] [10.1021/jm00385a001]

4. Bagli J, Bogri T, Palameta B, Rakhit S, Peseckis S, McQuillan J, Lee DK..  (1988)  Chemistry and positive inotropic effect of pelrinone and related derivatives. A novel class of 2-methylpyrimidones as inotropic agents.,  31  (4): [PMID:2832602] [10.1021/jm00399a023]

5. Berellini G, Springer C, Waters NJ, Lombardo F..  (2009)  In silico prediction of volume of distribution in human using linear and nonlinear models on a 669 compound data set.,  52  (14): [PMID:19603833] [10.1021/jm9004658]

6. Ward KW, Nagilla R, Jolivette LJ..  (2005)  Comparative evaluation of oral systemic exposure of 56 xenobiotics in rat, dog, monkey and human.,  35  (2): [PMID:16019946] [10.1080/00498250400028197]

7. Jolivette LJ, Ward KW..  (2005)  Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.,  94  (7): [PMID:15920768] [10.1002/jps.20373]

8. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

Source

Source(2):

• Scientific Literature
• IMI-CARE SARS-CoV-2 Data