2-(3,4-Dihydroxybenzylidenyl)-3-(3,4-dihydroxyphenyl)-4-hydroxypentanedioic acid

ID: ALA3112597

PubChem CID: 57620293

Max Phase: Preclinical

Molecular Formula: C18H16O9

Molecular Weight: 376.32

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H16O9/c19-11-3-1-8(6-13(11)21)5-10(17(24)25)15(16(23)18(26)27)9-2-4-12(20)14(22)7-9/h1-7,15-16,19-23H,(H,24,25)(H,26,27)/b10-5-

Standard InChI Key:  GRVCQHNOZLCUEA-YHYXMXQVSA-N

Molfile:  

     RDKit          2D

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    6.6640   -4.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3788   -5.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0952   -4.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0924   -4.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3770   -3.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9492   -5.2475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9506   -3.5959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8104   -5.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8116   -6.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5268   -6.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0979   -6.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3813   -6.0746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0976   -7.3110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5281   -7.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2406   -6.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9557   -6.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2393   -5.2443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9581   -7.3064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6706   -6.0678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8156   -7.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8166   -8.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5322   -8.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2485   -8.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2439   -7.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5346   -9.7800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1026   -8.9561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  1  8  1  0
  4  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
 11 15  1  0
 11 16  1  0
 16 17  1  0
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 17 19  1  0
 17 20  2  0
 15 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 15  1  0
 23 26  1  0
 22 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3112597

   (2Z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic 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: 376.32

Molecular Weight (Monoisotopic): 376.0794

AlogP: 1.21

#Rotatable Bonds: 6

Polar Surface Area: 175.75

Molecular Species: ACID

HBA: 7

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.54

CX Basic pKa: ┄

CX LogP: 1.51

CX LogD: -5.45

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.29

Np Likeness Score: 0.88

References

1. Chen YS, Yu HM, Shie JJ, Cheng TJ, Wu CY, Fang JM, Wong CH..  (2014)  Chemical constituents of Plectranthus amboinicus and the synthetic analogs possessing anti-inflammatory activity.,  22  (5): [PMID:24491635] [10.1016/j.bmc.2014.01.009]

Source

Source(1):

• Scientific Literature