4-Chloro-6-[4-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-5-methyl-1H-pyrazol-3-yl]-benzene-1,3-diol

ID: ALA191074

PubChem CID: 135425202

Max Phase: Preclinical

Molecular Formula: C18H15ClN2O4

Molecular Weight: 358.78

Molecule Type: Small molecule

Names and Identifiers

Synonyms: CCT072440

Canonical SMILES:  Cc1[nH]nc(-c2cc(Cl)c(O)cc2O)c1-c1ccc2c(c1)OCCO2

Standard InChI:  InChI=1S/C18H15ClN2O4/c1-9-17(10-2-3-15-16(6-10)25-5-4-24-15)18(21-20-9)11-7-12(19)14(23)8-13(11)22/h2-3,6-8,22-23H,4-5H2,1H3,(H,20,21)

Standard InChI Key:  RTIAXUYLACAMGU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   13.0902   -4.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0891   -5.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8039   -5.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5203   -5.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5175   -4.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8021   -4.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7996   -3.2955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3743   -5.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8087   -6.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1412   -7.0833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3959   -7.8680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2210   -7.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4760   -7.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2553   -6.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8682   -7.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2066   -5.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4250   -6.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7058   -8.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8246   -6.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6507   -7.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2560   -7.6734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0387   -7.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2126   -6.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6037   -6.0669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2304   -4.1145    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
 13  9  1  0
  3  9  1  0
  1  2  2  0
  6  7  1  0
 14 15  2  0
 15 20  1  0
  3  4  2  0
 19 16  1  0
  2  8  1  0
 16 17  2  0
 17 14  1  0
 13 14  1  0
  9 10  2  0
 12 18  1  0
 19 20  2  0
  4  5  1  0
  2  3  1  0
  5  6  2  0
  6  1  1  0
 10 11  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 11 12  1  0
  5 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA191074

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 358.78

Molecular Weight (Monoisotopic): 358.0720

AlogP: 3.89

#Rotatable Bonds: 2

Polar Surface Area: 87.60

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.43

CX Basic pKa: 2.51

CX LogP: 3.67

CX LogD: 3.37

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.65

Np Likeness Score: -0.51

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]

2. Dymock BW, Barril X, Brough PA, Cansfield JE, Massey A, McDonald E, Hubbard RE, Surgenor A, Roughley SD, Webb P, Workman P, Wright L, Drysdale MJ..  (2005)  Novel, potent small-molecule inhibitors of the molecular chaperone Hsp90 discovered through structure-based design.,  48  (13): [PMID:15974572] [10.1021/jm050355z]

3. Taldone T, Sun W, Chiosis G..  (2009)  Discovery and development of heat shock protein 90 inhibitors.,  17  (6): [PMID:19017562] [10.1016/j.bmc.2008.10.087]

4. Vo CD, Shebert HL, Zikovich S, Dryer RA, Huang TP, Moran LJ, Cho J, Wassarman DR, Falahee BE, Young PD, Gu GH, Heinl JF, Hammond JW, Jackvony TN, Frederick TE, Blair JA..  (2017)  Repurposing Hsp90 inhibitors as antibiotics targeting histidine kinases.,  27  (23): [PMID:29110989] [10.1016/j.bmcl.2017.10.036]

Source

Source(1):

• Scientific Literature