(Z)-3-{3-(2-Carboxy-ethyl)-4-[6-(4-methoxy-phenyl)-hex-5-enyloxy]-benzoyl}-benzoic acid

ID: ALA2114991

PubChem CID: 14739808

Max Phase: Preclinical

Molecular Formula: C30H30O7

Molecular Weight: 502.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C\CCCCOc2ccc(C(=O)c3cccc(C(=O)O)c3)cc2CCC(=O)O)cc1

Standard InChI:  InChI=1S/C30H30O7/c1-36-26-14-10-21(11-15-26)7-4-2-3-5-18-37-27-16-12-24(19-22(27)13-17-28(31)32)29(33)23-8-6-9-25(20-23)30(34)35/h4,6-12,14-16,19-20H,2-3,5,13,17-18H2,1H3,(H,31,32)(H,34,35)/b7-4-

Standard InChI Key:  SYZSSLLFRVDRHL-DAXSKMNVSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2114991

   3-[3-(2-carboxyethyl)-4-[(Z)-6-(4-methoxyphenyl)hex-5-enoxy]benzoyl]benzoic acid

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: 502.56

Molecular Weight (Monoisotopic): 502.1992

AlogP: 5.90

#Rotatable Bonds: 14

Polar Surface Area: 110.13

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.46

CX Basic pKa: ┄

CX LogP: 6.37

CX LogD: -0.17

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.21

Np Likeness Score: 0.17

References

1. Gapinski DM, Mallett BE, Froelich LL, Jackson WT..  (1990)  Benzophenone dicarboxylic acid antagonists of leukotriene B4. 2. Structure-activity relationships of the lipophilic side chain.,  33  (10): [PMID:2170648] [10.1021/jm00172a020]

2. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

Source

Source(2):

• Scientific Literature
• Fraunhofer HDAC6