US9187406, Compound 1

ID: ALA3915135

PubChem CID: 49778910

Max Phase: Preclinical

Molecular Formula: C23H22O8

Molecular Weight: 426.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C(C(=O)/C=C/c1ccc(O)c(OC)c1)C(=O)/C=C/c1ccc(O)c(OC)c1

Standard InChI:  InChI=1S/C23H22O8/c1-29-20-12-14(4-8-16(20)24)6-10-18(26)22(23(28)31-3)19(27)11-7-15-5-9-17(25)21(13-15)30-2/h4-13,22,24-25H,1-3H3/b10-6+,11-7+

Standard InChI Key:  GYWBYEKCMUYXGS-JMQWPVDRSA-N

Molfile:  

     RDKit          2D

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    2.5912   -7.5095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5524   -5.4086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336   -3.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4833   -9.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7798  -10.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7746  -12.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4729  -12.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4688  -13.9657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1765  -12.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8726  -12.7545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8363  -12.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1817  -10.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  5 19  1  0
 19 20  2  0
 19 21  1  0
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 22 23  1  0
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 28 31  2  0
 31 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3915135

   methyl (E)-5-(4-hydroxy-3-methoxyphenyl)-2-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-3-oxopent-4-enoate

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: 426.42

Molecular Weight (Monoisotopic): 426.1315

AlogP: 2.77

#Rotatable Bonds: 9

Polar Surface Area: 119.36

Molecular Species: ACID

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.54

CX Basic pKa: ┄

CX LogP: 4.01

CX LogD: 2.43

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.36

Np Likeness Score: 0.39

References

1.  (2015)  Curcumin analogues as zinc chelators and their uses, 

Source

Source(1):

• BindingDB Database