ID: ALA86889

Max Phase: Preclinical

Molecular Formula: C14H15N3O4S

Molecular Weight: 321.36

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCOC(=O)C1=C(C)N=C(S)NC1c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C14H15N3O4S/c1-3-21-13(18)11-8(2)15-14(22)16-12(11)9-5-4-6-10(7-9)17(19)20/h4-7,12H,3H2,1-2H3,(H2,15,16,22)

Standard InChI Key:  TWRZPKOGAMULBM-UHFFFAOYSA-N

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

Properties

Molecular Weight: 321.36

Molecular Weight (Monoisotopic): 321.0783

AlogP: 2.36

#Rotatable Bonds: 4

Polar Surface Area: 93.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 6.82

CX Basic pKa: 5.63

CX LogP: 2.58

CX LogD: 2.17

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.38

Np Likeness Score: -1.34

References

1. Atwal KS, Rovnyak GC, Kimball SD, Floyd DM, Moreland S, Swanson BN, Gougoutas JZ, Schwartz J, Smillie KM, Malley MF..  (1990)  Dihydropyrimidine calcium channel blockers. 2. 3-substituted-4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potent mimics of dihydropyridines.,  33  (9): [PMID:2391701] [10.1021/jm00171a044]

2. Rovnyak GC, Atwal KS, Hedberg A, Kimball SD, Moreland S, Gougoutas JZ, O'Reilly BC, Schwartz J, Malley MF..  (1992)  Dihydropyrimidine calcium channel blockers. 4. Basic 3-substituted-4-aryl-1,4-dihydropyrimidine-5-carboxylic acid esters. Potent antihypertensive agents.,  35  (17): [PMID:1387168] [10.1021/jm00095a023]

3. Damgaard M, Al-Khawaja A, Nittegaard-Nielsen M, Petersen RF, Wellendorph P, Frølund B..  (2017)  Monastrol, a 3,4-dihydropyrimidin-2(1H)-thione, as structural scaffold for the development of modulators for GHB high-affinity binding sites and α1β2δ GABAA receptors.,  138  [PMID:28683403] [10.1016/j.ejmech.2017.06.024]

4. González-Hernández E, Aparicio R, Garayoa M, Montero MJ, Sevilla MÁ, Pérez-Melero C..  (2019)  Dihydropyrimidine-2-thiones as Eg5 inhibitors and L-type calcium channel blockers: potential antitumour dual agents.,  10  (9): [PMID:31673316] [10.1039/C9MD00108E]

Source

Source(1):

• Scientific Literature