ID: ALA333928

Max Phase: Preclinical

Molecular Formula: C11H10N6O

Molecular Weight: 242.24

Molecule Type: Small molecule

Associated Items:

Representations

Canonical SMILES:  Nc1nc(OCc2ccccc2)c2[nH]nnc2n1

Standard InChI:  InChI=1S/C11H10N6O/c12-11-13-9-8(15-17-16-9)10(14-11)18-6-7-4-2-1-3-5-7/h1-5H,6H2,(H3,12,13,14,15,16,17)

Standard InChI Key:  ZHTBAYPUCDCQPX-UHFFFAOYSA-N

Associated Targets(Human)

6-O-methylguanine-DNA methyltransferase 451 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Myeloperoxidase 1002 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Thyroid peroxidase 64 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Lactoperoxidase 15 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Eosinophil peroxidase 8 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Cytochrome P450 3A4 53859 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Cytochrome P450 1A2 26471 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Cytochrome P450 2B6 1338 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Cytochrome P450 2C8 1492 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Cytochrome P450 2D6 33882 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Eosinophil peroxidase 2 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Mus musculus 284745 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Properties

Molecular Weight: 242.24Molecular Weight (Monoisotopic): 242.0916AlogP: 0.91#Rotatable Bonds: 3
Polar Surface Area: 102.60Molecular Species: NEUTRALHBA: 6HBD: 2
#RO5 Violations: 0HBA (Lipinski): 7HBD (Lipinski): 3#RO5 Violations (Lipinski): 0
CX Acidic pKa: 7.81CX Basic pKa: 0.41CX LogP: 1.71CX LogD: 1.57
Aromatic Rings: 3Heavy Atoms: 18QED Weighted: 0.71Np Likeness Score: -1.04

References

1. Chae MY, Swenn K, Kanugula S, Dolan ME, Pegg AE, Moschel RC..  (1995)  8-Substituted O6-benzylguanine, substituted 6(4)-(benzyloxy)pyrimidine, and related derivatives as inactivators of human O6-alkylguanine-DNA alkyltransferase.,  38  (2): [PMID:7830279] [10.1021/jm00002a018]
2. Reinhard J, Hull WE, von der Lieth CW, Eichhorn U, Kliem HC, Kaina B, Wiessler M..  (2001)  Monosaccharide-linked inhibitors of O(6)-methylguanine-DNA methyltransferase (MGMT): synthesis, molecular modeling, and structure-activity relationships.,  44  (24): [PMID:11708909] [10.1021/jm010006e]
3. Duclos F, Abell LM, Harden DG, Pike K, Nowak K, Locke GA, Duke GJ, Liu X, Fernando G, Shaw SA, Vokits BP, Wurtz NR, Viet A, Valente MN, Stachura S, Sleph P, Khan JA, Gao J, Dongre AR, Zhao L, Wexler RR, Gordon DA, Kick EK..  (2017)  Triazolopyrimidines identified as reversible myeloperoxidase inhibitors.,  (11): [PMID:30108726] [10.1039/C7MD00268H]
4. Wurtz NR, Viet A, Shaw SA, Dilger A, Valente MN, Khan JA, Jusuf S, Narayanan R, Fernando G, Lo F, Liu X, Locke GA, Kopcho L, Abell LM, Sleph P, Basso M, Zhao L, Wexler RR, Duclos F, Kick EK..  (2018)  Potent Triazolopyridine Myeloperoxidase Inhibitors.,  (12): [PMID:30613322] [10.1021/acsmedchemlett.8b00308]
5. Shaw SA,Vokits BP,Dilger AK,Viet A,Clark CG,Abell LM,Locke GA,Duke G,Kopcho LM,Dongre A,Gao J,Krishnakumar A,Jusuf S,Khan J,Spronk SA,Basso MD,Zhao L,Cantor GH,Onorato JM,Wexler RR,Duclos F,Kick EK.  (2020)  Discovery and structure activity relationships of 7-benzyl triazolopyridines as stable, selective, and reversible inhibitors of myeloperoxidase.,  28  (22): [PMID:33007547] [10.1016/j.bmc.2020.115723]

Source