3,4,5-triacetylbenzoic acid

ID: ALA505054

Cas Number: 6635-24-1

PubChem CID: 95088

Max Phase: Preclinical

Molecular Formula: C13H12O8

Molecular Weight: 296.23

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3,4,5-Triacetylbenzoic Acid | 6635-24-1|3,4,5-triacetoxybenzoic acid|3,4,5-tris(acetyloxy)benzoic acid|3,4,5-triacetyloxybenzoic acid|3,4,5-Triacetoxy-benzoic acid|Benzoic acid, 3,4,5-tris(acetyloxy)-|NSC-16959|NSC-49173|Benzoic acid,3,4,5-tris(acetyloxy)-|NSC 49173|Triacetylgallussaure|NSC 16959|Gallic acid, triacetate|2TPZ8W7SN9|GALLIC ACID TRIACETATE|3,4,5-triacetylbenzoic acid|SCHEMBL716891|CHEMBL505054|DTXSID40216562|BJCGLAAQSUGMKB-UHFFFAOYSA-N|NSC16959|NSC49173|STR05114|MFCD00017226|AKOS00Show More⌵

Canonical SMILES:  CC(=O)Oc1cc(C(=O)O)cc(OC(C)=O)c1OC(C)=O

Standard InChI:  InChI=1S/C13H12O8/c1-6(14)19-10-4-9(13(17)18)5-11(20-7(2)15)12(10)21-8(3)16/h4-5H,1-3H3,(H,17,18)

Standard InChI Key:  BJCGLAAQSUGMKB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
    3.4204    1.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4204    0.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1348   -0.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8493    0.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8493    1.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1348    1.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1348    2.2908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7059    1.4658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7059   -0.1842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5638   -0.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2783    0.2283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5638   -1.0092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4204    2.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7059    2.2908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4204    3.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9914    1.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9914    0.2283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770    1.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7059   -1.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9914   -1.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4204   -1.4217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 10 11  2  0
  5  6  2  0
 10 12  1  0
  6  1  1  0
  7 13  1  0
  1  2  2  0
 13 14  2  0
  6  7  1  0
 13 15  1  0
  3  4  2  0
  8 16  1  0
  1  8  1  0
 16 17  2  0
 16 18  1  0
  2  9  1  0
  9 19  1  0
  4  5  1  0
 19 20  1  0
  4 10  1  0
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA505054

   3,4,5-TRIACETOXYBENZOIC ACID

Molecule Features

Natural Product: Yes

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: 296.23

Molecular Weight (Monoisotopic): 296.0532

AlogP: 1.16

#Rotatable Bonds: 4

Polar Surface Area: 116.20

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.76

CX Basic pKa: ┄

CX LogP: 0.45

CX LogD: -2.83

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.65

Np Likeness Score: 0.53

References

1. Leal PC, Mascarello A, Derita M, Zuljan F, Nunes RJ, Zacchino S, Yunes RA..  (2009)  Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi.,  19  (6): [PMID:19232493] [10.1016/j.bmcl.2009.01.061]

2. Sunnerheim K, Nordqvist A, Nordlander G, Borg-Karlson AK, Unelius CR, Bohman B, Nordenhem H, Hellqvist C, Karlén A..  (2007)  Quantitative structure-activity relationships of pine weevil antifeedants, a multivariate approach.,  55  (23): [PMID:17927202] [10.1021/jf070014p]

Source

Source(1):

• Scientific Literature