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4-Isopropyl-5-methoxy-2-[4-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-phenol

ID: ALA427158

PubChem CID: 136109081

Max Phase: Preclinical

Molecular Formula: C20H22N2O3

Molecular Weight: 338.41

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2c[nH]nc2-c2cc(C(C)C)c(OC)cc2O)cc1

Standard InChI:  InChI=1S/C20H22N2O3/c1-12(2)15-9-16(18(23)10-19(15)25-4)20-17(11-21-22-20)13-5-7-14(24-3)8-6-13/h5-12,23H,1-4H3,(H,21,22)

Standard InChI Key:  QHFZSMLTNOBUTA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -0.8125   -2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167   -2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0750   -3.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333   -1.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458   -2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -3.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3292   -1.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333   -3.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9625   -1.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167    0.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167    1.0208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208    0.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4958   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6833   -1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292    1.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  2  0
  5  2  1  0
  6  2  2  0
  7  5  2  0
  8  9  2  0
  9  6  1  0
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 13 12  1  0
 14 12  2  0
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 18 20  2  0
 19 13  2  0
 20 14  1  0
 21 18  1  0
 22 15  1  0
 23 15  1  0
 24 17  1  0
 25 21  1  0
 11 10  1  0
 19 18  1  0
  8  7  1  0
M  END

Alternative Forms

  1. Parent:

    ALA427158

    ---

Associated Targets(non-human)

HSP82 Heat shock protein HSP 90 (HSP82) (42 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

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 338.41Molecular Weight (Monoisotopic): 338.1630AlogP: 4.59#Rotatable Bonds: 5
Polar Surface Area: 67.37Molecular Species: NEUTRALHBA: 4HBD: 2
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 8.79CX Basic pKa: 2.10CX LogP: 4.58CX LogD: 4.57
Aromatic Rings: 3Heavy Atoms: 25QED Weighted: 0.71Np Likeness Score: -0.15

References

1. Cheung KM, Matthews TP, James K, Rowlands MG, Boxall KJ, Sharp SY, Maloney A, Roe SM, Prodromou C, Pearl LH, Aherne GW, McDonald E, Workman P..  (2005)  The identification, synthesis, protein crystal structure and in vitro biochemical evaluation of a new 3,4-diarylpyrazole class of Hsp90 inhibitors.,  15  (14): [PMID:15955698] [10.1016/j.bmcl.2005.05.046]

Source