5-((3-carboxy-5-methyl-4-oxocyclohexa-2,5-dienylidene)(2,6-dichloro-3-sulfophenyl)methyl)-2-hydroxy-3-methylbenzoic acid

ID: ALA1205573

PubChem CID: 6067962

Max Phase: Preclinical

Molecular Formula: C23H16Cl2O9S

Molecular Weight: 539.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C/C(=C(\c2cc(C)c(O)c(C(=O)O)c2)c2c(Cl)ccc(S(=O)(=O)O)c2Cl)C=C(C(=O)O)C1=O

Standard InChI:  InChI=1S/C23H16Cl2O9S/c1-9-5-11(7-13(20(9)26)22(28)29)17(12-6-10(2)21(27)14(8-12)23(30)31)18-15(24)3-4-16(19(18)25)35(32,33)34/h3-8,26H,1-2H3,(H,28,29)(H,30,31)(H,32,33,34)/b17-12-

Standard InChI Key:  GNKCWVPIWVNYKN-ATVHPVEESA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
    6.9625   -8.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4125   -6.5000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -6.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2542   -7.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -6.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5292   -8.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5292   -7.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9625   -5.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6750   -8.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4917   -7.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417   -5.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917   -5.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -7.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2292   -9.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3875   -8.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3750   -3.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6750   -9.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9417   -3.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8375   -4.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -7.3167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.1042   -4.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2542   -4.8417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -8.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1125   -6.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  9  2  0
  4  8  1  0
  5  7  1  0
  6 14  2  0
  7  4  1  0
  8  1  2  0
  9  5  1  0
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 11  7  2  0
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 16 18  1  0
 17  6  1  0
 18 19  2  0
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 20 30  2  0
 21  2  1  0
 22  5  2  0
 23  2  2  0
 24  2  2  0
 25 10  1  0
 26 15  1  0
 27 17  1  0
 28 15  2  0
 29 17  2  0
 30 22  1  0
 31  9  1  0
 32 16  2  0
 33 22  1  0
 34 12  1  0
 35 18  1  0
  4 13  2  0
  6 16  1  0
  3 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1205573

   5-[(Z)-(3-carboxy-5-methyl-4-oxocyclohexa-2,5-dien-1-ylidene)-(2,6-dichloro-3-sulfophenyl)methyl]-2-hydroxy-3-methylbenzoic 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: 539.35

Molecular Weight (Monoisotopic): 537.9892

AlogP: 4.29

#Rotatable Bonds: 5

Polar Surface Area: 166.27

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -2.54

CX Basic pKa: ┄

CX LogP: 5.35

CX LogD: -3.98

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.32

Np Likeness Score: 0.06

References

1. Hu Y,Wang L,Han X,Zhou Y,Zhang T,Wang L,Hong T,Zhang W,Guo XX,Sun J,Qi Y,Yu J,Liu H,Wu F.  (2019)  Discovery of a Bioactive Inhibitor with a New Scaffold for Cystathionine γ-Lyase.,  62  (3): [PMID:30562026] [10.1021/acs.jmedchem.8b01720]

Source

Source(1):

• Scientific Literature