isopropyl 4-(5-methyl-6-(2-methylpyridin-3-yloxy)pyrimidin-4-yloxy)piperidine-1-carboxylate

ID: ALA1766081

PubChem CID: 16036825

Max Phase: Preclinical

Molecular Formula: C20H26N4O4

Molecular Weight: 386.45

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  Cc1ncccc1Oc1ncnc(OC2CCN(C(=O)OC(C)C)CC2)c1C

Standard InChI:  InChI=1S/C20H26N4O4/c1-13(2)26-20(25)24-10-7-16(8-11-24)27-18-14(3)19(23-12-22-18)28-17-6-5-9-21-15(17)4/h5-6,9,12-13,16H,7-8,10-11H2,1-4H3

Standard InChI Key:  YHKUMVXEUWUPKX-UHFFFAOYSA-N

Molfile:  

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    1.4347   -0.7059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1528   -2.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5810   -1.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7261   -0.7097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0113   -0.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2932   -0.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -0.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1550   -0.7136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4439    0.5258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8706   -0.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5839   -0.7174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8728    0.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Associated Targets(Human)

GPR119 Tclin Glucose-dependent insulinotropic receptor (4762 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Liver (3974 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Gpr119 Glucose-dependent insulinotropic receptor (270 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

Calculated Properties

Molecular Weight: 386.45Molecular Weight (Monoisotopic): 386.1954AlogP: 3.67#Rotatable Bonds: 5
Polar Surface Area: 86.67Molecular Species: NEUTRALHBA: 7HBD:
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 5.44CX LogP: 2.65CX LogD: 2.65
Aromatic Rings: 2Heavy Atoms: 28QED Weighted: 0.77Np Likeness Score: -0.84

References

1. McClure KF, Darout E, Guimarães CR, DeNinno MP, Mascitti V, Munchhof MJ, Robinson RP, Kohrt J, Harris AR, Moore DE, Li B, Samp L, Lefker BA, Futatsugi K, Kung D, Bonin PD, Cornelius P, Wang R, Salter E, Hornby S, Kalgutkar AS, Chen Y..  (2011)  Activation of the G-protein-coupled receptor 119: a conformation-based hypothesis for understanding agonist response.,  54  (6): [PMID:21361292] [10.1021/jm200003p]
2. Xia Y, Chackalamannil S, Greenlee WJ, Jayne C, Neustadt B, Stamford A, Vaccaro H, Xu XL, Baker H, O'Neill K, Woods M, Hawes B, Kowalski T..  (2011)  Discovery of a nortropanol derivative as a potent and orally active GPR119 agonist for type 2 diabetes.,  21  (11): [PMID:21536438] [10.1016/j.bmcl.2011.04.035]
3. Semple G, Lehmann J, Wong A, Ren A, Bruce M, Shin YJ, Sage CR, Morgan M, Chen WC, Sebring K, Chu ZL, Leonard JN, Al-Shamma H, Grottick AJ, Du F, Liang Y, Demarest K, Jones RM..  (2012)  Discovery of a second generation agonist of the orphan G-protein coupled receptor GPR119 with an improved profile.,  22  (4): [PMID:22264481] [10.1016/j.bmcl.2011.12.092]
4. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]