N-Cyclopentyl-4-methyl-5-(2-((5-morpholinopyridin-2-yl)amino)-pyrimidin-4-yl)thiazol-2-amine

ID: ALA4081497

PubChem CID: 126535109

Max Phase: Preclinical

Molecular Formula: C22H27N7OS

Molecular Weight: 437.57

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  Cc1nc(NC2CCCC2)sc1-c1ccnc(Nc2ccc(N3CCOCC3)cn2)n1

Standard InChI:  InChI=1S/C22H27N7OS/c1-15-20(31-22(25-15)26-16-4-2-3-5-16)18-8-9-23-21(27-18)28-19-7-6-17(14-24-19)29-10-12-30-13-11-29/h6-9,14,16H,2-5,10-13H2,1H3,(H,25,26)(H,23,24,27,28)

Standard InChI Key:  UGKFAPJXEKVBHI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.0351  -10.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7169   -9.8078    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4866   -9.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9890   -8.3634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8065   -8.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2844   -9.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0694   -8.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0843   -8.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6658   -8.9909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0500  -11.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7842  -12.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5095  -12.7304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2253  -12.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2154  -11.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9266  -11.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6604  -11.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3713  -11.0459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3690  -10.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0799   -9.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7929  -10.2132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7986  -11.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0877  -11.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6661  -12.2914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9507  -12.7115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0758  -12.7463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3570  -12.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3420  -11.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

  1. Parent:

    ALA4081497

    ---

Associated Targets(Human)

CCNH Tbio Cyclin-dependent kinase 7/ cyclin H (714 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCNT1 Tchem CDK9/cyclin T1 (2643 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CDK2 Tchem CDK2/Cyclin A2 (2260 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CDK1 Tchem Cyclin-dependent kinase 1/cyclin B1 (1887 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCND3 Tchem CDK6/cyclin D3 (897 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CDK4 Tclin Cyclin-dependent kinase 4/cyclin D1 (2340 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MV4-11 (7307 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-453 (1139 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-468 (9477 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MOLM-13 (2241 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NB-4 (999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A2780 (11979 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LNCaP C4-2B (271 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-3 (62116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BPH-1 (107 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MRC5 (9203 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CDK4 Tclin Cyclin-dependent kinase 4/6 (19 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DYRK2 Tchem Dual-specificity tyrosine-phosphorylation regulated kinase 2 (2095 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DYRK3 Tchem Dual-specificity tyrosine-phosphorylation regulated kinase 3 (1018 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LIMK1 Tchem LIM domain kinase 1 (2329 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
STK16 Tchem Serine/threonine-protein kinase 16 (910 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Rattus norvegicus (775804 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

Calculated Properties

Molecular Weight: 437.57Molecular Weight (Monoisotopic): 437.1998AlogP: 4.24#Rotatable Bonds: 6
Polar Surface Area: 88.09Molecular Species: NEUTRALHBA: 9HBD: 2
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 11.34CX Basic pKa: 3.63CX LogP: 3.77CX LogD: 3.77
Aromatic Rings: 3Heavy Atoms: 31QED Weighted: 0.59Np Likeness Score: -1.84

References

1. Tadesse S, Yu M, Mekonnen LB, Lam F, Islam S, Tomusange K, Rahaman MH, Noll B, Basnet SK, Teo T, Albrecht H, Milne R, Wang S..  (2017)  Highly Potent, Selective, and Orally Bioavailable 4-Thiazol-N-(pyridin-2-yl)pyrimidin-2-amine Cyclin-Dependent Kinases 4 and 6 Inhibitors as Anticancer Drug Candidates: Design, Synthesis, and Evaluation.,  60  (5): [PMID:28156111] [10.1021/acs.jmedchem.6b01670]

Source