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1-[3-(4-Methyl-piperazin-1-yl)-propyl]-4-(3-thiophen-3-yl-pyrazolo[1,5-a]pyrimidin-6-yl)-1H-pyridin-2-one

ID: ALA118400

PubChem CID: 5329471

Max Phase: Preclinical

Molecular Formula: C23H26N6OS

Molecular Weight: 434.57

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  CN1CCN(CCCn2ccc(-c3cnc4c(-c5ccsc5)cnn4c3)cc2=O)CC1

Standard InChI:  InChI=1S/C23H26N6OS/c1-26-8-10-27(11-9-26)5-2-6-28-7-3-18(13-22(28)30)20-14-24-23-21(15-25-29(23)16-20)19-4-12-31-17-19/h3-4,7,12-17H,2,5-6,8-11H2,1H3

Standard InChI Key:  QZNBJKPMALDRGE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.8792   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667   -2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6000   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5792   -3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5375   -2.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2500   -6.0500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8000   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -0.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0792   -5.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0417   -5.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3125   -0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1958   -2.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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 24 18  1  0
M  END

Alternative Forms

Associated Targets(Human)

KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FLT1 Tclin Vascular endothelial growth factor receptor (287 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDGFRB Tclin VEGF-receptor 2 and PDGF-receptor beta (KDR and PDGFR beta) (29 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FLT1 Tclin Vascular endothelial growth factor receptor 1 and 2 (Flt-1 and KDR) (27 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FLT4 Tclin Vascular endothelial growth factor receptor 2 and 3 (KDR and Flt-4) (23 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDR Tclin VEGF-receptor 2 and Fibroblast growth factor receptor 1 (50 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDR Tclin VEGF-receptor 2 and Fibroblast growth factor receptor 2 (15 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SRC Tclin VEGF-receptor 2 and tyrosine-protein kinase SRC (25 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Rattus norvegicus (775804 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

Calculated Properties

Molecular Weight: 434.57Molecular Weight (Monoisotopic): 434.1889AlogP: 2.92#Rotatable Bonds: 6
Polar Surface Area: 58.67Molecular Species: NEUTRALHBA: 8HBD:
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 8.10CX LogP: 1.79CX LogD: 1.01
Aromatic Rings: 4Heavy Atoms: 31QED Weighted: 0.47Np Likeness Score: -2.10

References

1. Fraley ME, Rubino RS, Hoffman WF, Hambaugh SR, Arrington KL, Hungate RW, Bilodeau MT, Tebben AJ, Rutledge RZ, Kendall RL, McFall RC, Huckle WR, Coll KE, Thomas KA..  (2002)  Optimization of a pyrazolo[1,5-a]pyrimidine class of KDR kinase inhibitors: improvements in physical properties enhance cellular activity and pharmacokinetics.,  12  (24): [PMID:12443771] [10.1016/s0960-894x(02)00827-2]

Source