2-Amino-6-[3-(3,5-dimethoxy-phenoxy)-propylamino]-5-nitroso-3H-pyrimidin-4-one

ID: ALA159139

Chembl Id: CHEMBL159139

PubChem CID: 136055810

Max Phase: Preclinical

Molecular Formula: C15H19N5O5

Molecular Weight: 349.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)cc(OCCCNc2nc(N)nc(O)c2N=O)c1

Standard InChI:  InChI=1S/C15H19N5O5/c1-23-9-6-10(24-2)8-11(7-9)25-5-3-4-17-13-12(20-22)14(21)19-15(16)18-13/h6-8H,3-5H2,1-2H3,(H4,16,17,18,19,21)

Standard InChI Key:  WGFQHVGQLDHRRT-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA159139

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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: 349.35

Molecular Weight (Monoisotopic): 349.1386

AlogP: 2.06

#Rotatable Bonds: 9

Polar Surface Area: 141.18

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.91

CX Basic pKa: 2.80

CX LogP: 2.37

CX LogD: 2.37

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.46

Np Likeness Score: -0.57

References

1. Lever OW, Bell LN, Hyman C, McGuire HM, Ferone R..  (1986)  Inhibitors of dihydropteroate synthase: substituent effects in the side-chain aromatic ring of 6-[[3-(aryloxy)propyl]amino]-5-nitrosoisocytosines and synthesis and inhibitory potency of bridged 5-nitrosoisocytosine-p-aminobenzoic acid analogues.,  29  (5): [PMID:3486292] [10.1021/jm00155a014]

2. Zhou W, Scocchera EW, Wright DL, Anderson AC.  (2013)  Antifolates as effective antimicrobial agents: new generations of trimethoprim analogs,  4  (6): [10.1039/C3MD00104K]

Source

Source(1):

• Scientific Literature