demethylenated piperic acid

ID: ALA507378

Cas Number: 110501-70-7

PubChem CID: 19888955

Max Phase: Preclinical

Molecular Formula: C11H10O4

Molecular Weight: 206.20

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Demethylenated Piperic Acid | 3'-Hydroxyavenalumic acid|5F380S5YI8|(2E,4E)-5-(3,4-Dihydroxyphenyl)-2,4-pentadienoic acid|UNII-5F380S5YI8|110501-70-7|1073666-65-5|2,4-Pentadienoic acid, 5-(3,4-dihydroxyphenyl)-, (2E,4E)-|(2E,4E)-5-(3,4-dihydroxyphenyl)penta-2,4-dienoic acid|2,4-Pentadienoic acid, 5-(3,4-dihydroxyphenyl)- (9CI)|5-(3,4-DIHYDROXYPHENYL)PENTA-2,4-DIENOIC ACID|demethylenated piperic acid|CHEMBL507378|SCHEMBL9654233

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

Standard InChI:  InChI=1S/C11H10O4/c12-9-6-5-8(7-10(9)13)3-1-2-4-11(14)15/h1-7,12-13H,(H,14,15)/b3-1+,4-2+

Standard InChI Key:  QJTJIOCQLSVOMY-ZPUQHVIOSA-N

Molfile:  

     RDKit          2D

 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.7836   -4.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0672   -4.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0700   -3.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7854   -3.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4984   -4.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4972   -3.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -3.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6411   -3.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0718   -3.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7878   -3.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5008   -3.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168   -3.6593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4976   -2.4245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2132   -4.9184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2114   -3.2647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
  3  4  2  0
  8  9  1  0
  4  6  1  0
  9 10  2  0
  5  6  2  0
 10 11  1  0
  1  2  2  0
 11 12  1  0
  5  1  1  0
 11 13  2  0
  2  3  1  0
  5 14  1  0
  3  7  1  0
  6 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA507378

   DEMETHYLENATED PIPERIC 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: 206.20

Molecular Weight (Monoisotopic): 206.0579

AlogP: 1.75

#Rotatable Bonds: 3

Polar Surface Area: 77.76

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.75

CX Basic pKa: ┄

CX LogP: 2.06

CX LogD: -1.23

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.40

Np Likeness Score: 1.41

References

1. Dubey SK, Sharma AK, Narain U, Misra K, Pati U..  (2008)  Design, synthesis and characterization of some bioactive conjugates of curcumin with glycine, glutamic acid, valine and demethylenated piperic acid and study of their antimicrobial and antiproliferative properties.,  43  (9): [PMID:18201805] [10.1016/j.ejmech.2007.11.027]

2. Chavarria D, Silva T, Martins D, Bravo J, Summavielle T, Garrido J, Borges F.  (2015)  Exploring cinnamic acid scaffold: development of promising neuroprotective lipophilic antioxidants,  6  (6): [10.1039/C5MD00018A]

Source

Source(1):

• Scientific Literature