Np mrd loader

Showing NP-Card for Ethyl gallate (NP0047758)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-03-17 20:45:28 UTC
Updated at2022-03-17 20:45:29 UTC
NP-MRD IDNP0047758
Secondary Accession NumbersNone
Natural Product Identification
Common NameEthyl gallate
DescriptionEthyl gallate, also known as ethyl gallic acid or E313, belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid. A gallate ester obtained by the formal condensation of gallic acid with ethanol. Ethyl gallate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Ethyl gallate is found, on average, in the highest concentration within grape wines and vinegars. Ethyl gallate has also been detected, but not quantified in, fruits and guava. Ethyl gallate is found in Acacia arabica , Acalypha hispida, Acer ginnala, Acer negundo, Acer oblongum, Acer rubrum L. , Acer truncatum, Ailanthus altissima, Alchornea glandulosa, Ampelopsis brevipedunculata , Anacardium occidentale, Pithecellobium clypearia, Bombax malabaricum , Canarium album, Castanea mollissima , Dimocarpus longan, Elaeocarpus tuberculatus, Euphorbia ferganensis, Euphorbia nutans, Excoecaria agallocha, Haematoxylon campechianum , Haematoxylum campechianum, Koelreuteria paniculata, Limonium axillare, Mabea fistulifera, Nymphaea alba, Nymphaea caerulea, Oxalis corniculata , Paeonia anomala, Phyllanthus emblica , Phyllanthus niruri, Phyllanthus sellowianus, Phyllanthus urinaria, Pistacia mexicana, Pistacia weinmannifolia J.Pisson ex.Franch , Rhodiola crenulata, Rhodiola fastigiata, Rhodiola sacra, Rhus chinensis, Rhus coriaria , Syzygium cumini, Tagetes ercta, Terminalia arjuna, Terminalia chebula , Terminalia myriocarpa, Toona sinensis, Toxicodendron vernicifluum and Vitis vinifera. Ethyl gallate was first documented in 1999 (PMID: 10543436). This could make ethyl gallate a potential biomarker for the consumption of these foods (PMID: 24533783) (PMID: 25104086) (PMID: 26137691) (PMID: 16444672).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047758 (Ethyl gallate)


  Mrv1652310041917452D          

 14 14  0  0  0  0            999 V2000
   -0.6250    1.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395    1.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395    0.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250   -0.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0893    0.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0893    1.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250   -0.8465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8039    1.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8039    2.4537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5184    1.2162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2330    1.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9474    1.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0541   -0.0213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0541    1.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  8  1  0  0  0  0
 11 12  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8  9  2  0  0  0  0
  4  7  1  0  0  0  0
  2 14  1  0  0  0  0
  3 13  1  0  0  0  0
M  END
Download

3D MOL for NP0047758 (Ethyl gallate)

Download
3D SDF for NP0047758 (Ethyl gallate)

  Mrv1652310041917452D          

 14 14  0  0  0  0            999 V2000
   -0.6250    1.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395    1.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395    0.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250   -0.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0893    0.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0893    1.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250   -0.8465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8039    1.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8039    2.4537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5184    1.2162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2330    1.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9474    1.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0541   -0.0213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0541    1.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  8  1  0  0  0  0
 11 12  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8  9  2  0  0  0  0
  4  7  1  0  0  0  0
  2 14  1  0  0  0  0
  3 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047758

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O5/c1-2-14-9(13)5-3-6(10)8(12)7(11)4-5/h3-4,10-12H,2H2,1H3

> <INCHI_KEY>
VFPFQHQNJCMNBZ-UHFFFAOYSA-N

> <FORMULA>
C9H10O5

> <MOLECULAR_WEIGHT>
198.174

> <EXACT_MASS>
198.052823422

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.084336058434445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.48

> <JCHEM_LOGP>
1.4228347696666663

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.285099370522756

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.11005930851721

> <JCHEM_PKA_STRONGEST_BASIC>
-5.548889272896791

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
48.7746

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl gallate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0047758 (Ethyl gallate)
Download
PDB for NP0047758 (Ethyl gallate)
HEADER    PROTEIN                                 04-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-OCT-19         0                                  
HETATM    1  C   UNK     0      -1.167   3.040   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.500   2.270   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.500   0.730   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.167  -0.040   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.167   0.730   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.167   2.270   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.167  -1.580   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.501   3.040   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.501   4.580   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.834   2.270   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.168   3.040   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.502   2.270   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.834  -0.040   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -3.834   3.040   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   14                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    8                                                  
CONECT    7    4                                                            
CONECT    8    6   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   12   10                                                       
CONECT   12   11                                                            
CONECT   13    3                                                            
CONECT   14    2                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

Download
3D PDB for NP0047758 (Ethyl gallate)
Download
SMILES for NP0047758 (Ethyl gallate)
CCOC(=O)C1=CC(O)=C(O)C(O)=C1
Download
INCHI for NP0047758 (Ethyl gallate)
InChI=1S/C9H10O5/c1-2-14-9(13)5-3-6(10)8(12)7(11)4-5/h3-4,10-12H,2H2,1H3
Download
View in JSmol
Synonyms
ValueSource
Ethyl gallic acidGenerator
Ethyl 3,4,5-trihydroxybenzoateHMDB
e313HMDB
3,4,5-Trihydroxybenzoic acid ethyl esterHMDB
EthylgallateHMDB
Gallic acid ethyl esterHMDB
NIPA 48HMDB
Nipagallin aHMDB
PhyllemblinHMDB
Progallin aHMDB
Ethyl gallateHMDB
Chemical FormulaC9H10O5
Average Mass198.1740 Da
Monoisotopic Mass198.05282 Da
IUPAC Nameethyl 3,4,5-trihydroxybenzoate
Traditional Nameethyl gallate
CAS Registry Number831-61-8
SMILES
CCOC(=O)C1=CC(O)=C(O)C(O)=C1
InChI Identifier
InChI=1S/C9H10O5/c1-2-14-9(13)5-3-6(10)8(12)7(11)4-5/h3-4,10-12H,2H2,1H3
InChI KeyVFPFQHQNJCMNBZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acacia arabicaPlant
Acalypha hispidaLOTUS Database
Acer ginnalaPlant
Acer negundoLOTUS Database
Acer oblongumLOTUS Database
Acer rubrumPlant
Acer truncatumLOTUS Database
Ailanthus altissimaLOTUS Database
Alchornea glandulosaLOTUS Database
Ampelopsis brevipedunculataPlant
Anacardium occidentaleLOTUS Database
Archidendron clypeariaLOTUS Database
Bombax ceibaPlant
Canarium albumLOTUS Database
Castanea mollissimaPlant
Dimocarpus longanLOTUS Database
Elaeocarpus tuberculatusLOTUS Database
Euphorbia ferganensisLOTUS Database
Euphorbia nutansLOTUS Database
Excoecaria agallochaLOTUS Database
Haematoxylon campechianum-
Haematoxylum campechianumLOTUS Database
Koelreuteria paniculataLOTUS Database
Limonium axillareLOTUS Database
Mabea fistuliferaLOTUS Database
Nymphaea albaLOTUS Database
Nymphaea caeruleaPlant
Oxalis corniculataPlant
Paeonia anomalaLOTUS Database
Phyllanthus emblicaPlant
Phyllanthus niruriLOTUS Database
Phyllanthus sellowianusLOTUS Database
Phyllanthus urinariaLOTUS Database
Pistacia mexicanaLOTUS Database
Pistacia weinmannifolia J.Pisson ex.FranchPlant
Psidium guajavaFooDB
Rhodiola crenulataPlant
Rhodiola fastigiataLOTUS Database
Rhodiola sacraPlant
Rhus chinensisLOTUS Database
Rhus coriariaPlant
Syzygium cuminiLOTUS Database
Tagetes erctaPlant
Terminalia arjunaLOTUS Database
Terminalia chebulaPlant
Terminalia myriocarpaLOTUS Database
Toona sinensisLOTUS Database
Toxicodendron vernicifluumLOTUS Database
Vitis viniferaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentGalloyl esters  
Alternative Parents
Substituents
  • Galloyl ester
    • 

  • P-hydroxybenzoic acid alkyl ester
    • 

  • M-hydroxybenzoic acid ester
    • 

  • P-hydroxybenzoic acid ester
    • 

  • Benzoate ester
    • 

  • Benzenetriol
    • 

  • Pyrogallol derivative
    • 

  • Benzoyl
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Polyol
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.48ALOGPS
logP1.42ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)8.11ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.77 m³·mol⁻¹ChemAxon
Polarizability19.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033836  
DrugBank IDNot Available
Phenol Explorer Compound ID439  
FoodDB IDFDB012004  
KNApSAcK IDC00030222  
Chemspider ID12693  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl gallate  
METLIN IDNot Available
PubChem Compound13250  
PDB IDNot Available
ChEBI ID87247  
Good Scents IDNot Available
References
General References
  1. Tseng HC, Wu WT, Huang HS, Wu MC: Antimicrobial activities of various fractions of longan (Dimocarpus longan Lour. Fen Ke) seed extract. Int J Food Sci Nutr. 2014 Aug;65(5):589-93. doi: 10.3109/09637486.2014.886181. Epub 2014 Feb 17. [PubMed:24533783  ] 
  2. Mohan S, Thiagarajan K, Chandrasekaran R: In vitro evaluation of antiproliferative effect of ethyl gallate against human oral squamous carcinoma cell line KB. Nat Prod Res. 2015;29(4):366-9. doi: 10.1080/14786419.2014.942303. Epub 2014 Aug  7. [PubMed:25104086  ] 
  3. Ning DS, Yan XX, Huang SS, Cheng L, Li J, Pan ZH: [Studies on chemical constituents of Zhuang medicine Excoecaria venenata and their cytotoxic activity]. Zhongguo Zhong Yao Za Zhi. 2015 Feb;40(4):686-90. [PubMed:26137691  ] 
  4. Mori T, Chang C, Maurtua D, Hammond GB: Isolation of the active compound in Mauria heterophylla, a Peruvian plant with antibacterial activity. Phytother Res. 2006 Feb;20(2):160-1. doi: 10.1002/ptr.1825. [PubMed:16444672  ] 
  5. Paulino N, Pizollatti MG, Yunes RA, Filho VC, Creczynski-Pasa TB, Calixto JB: The mechanisms underlying the relaxant effect of methyl and ethyl gallates in the guinea pig trachea in vitro: contribution of potassium channels. Naunyn Schmiedebergs Arch Pharmacol. 1999 Sep;360(3):331-6. doi: 10.1007/s002109900081. [PubMed:10543436  ]