NP-MRD: Showing NP-Card for butyl gallate (NP0165631)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 00:49:52 UTC

Updated at

2022-09-03 00:49:52 UTC

NP-MRD ID

NP0165631

Secondary Accession Numbers

None

Natural Product Identification

Common Name

butyl gallate

Description

BUTYL GALLATE, also known as butyl gallic acid or N-butyl gallate, 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. butyl gallate is found in Alchornea glandulosa. butyl gallate was first documented in 2017 (PMID: 27623150). Based on a literature review a small amount of articles have been published on BUTYL GALLATE (PMID: 35842178) (PMID: 34614054) (PMID: 31123307).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
    4.7882    0.6869    0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4287   -0.7595    0.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9777   -0.8103    0.7135 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1558   -0.1925   -0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7978   -0.2266   -0.0084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1882    0.2750   -0.8359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351    0.7664   -1.9480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5742    0.2174   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6031    0.7093   -1.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118    0.6578   -0.7731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9355    1.1506   -1.5733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1936    0.1065    0.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4820    0.0140    0.9513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1517   -0.3880    1.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4603   -0.9326    2.4753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8461   -0.3367    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8328    0.8922   -1.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8321    0.8263    0.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0798    1.3965    0.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4856   -1.3274   -0.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0884   -1.2416    1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6137   -1.8398    0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8093   -0.1905    1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2446   -0.8677   -1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4714    0.8402   -0.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4020    1.1441   -2.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8946    1.1304   -1.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2816    0.3310    0.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847   -1.3081    3.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0315   -0.7234    1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16  8  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  9 26  1  0
 11 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
M  END


  Mrv1652309032202492D          

 16 16  0  0  0  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  8 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0165631

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O5/c1-2-3-4-16-11(15)7-5-8(12)10(14)9(13)6-7/h5-6,12-14H,2-4H2,1H3

> <INCHI_KEY>
XOPOEBVTQYAOSV-UHFFFAOYSA-N

> <FORMULA>
C11H14O5

> <MOLECULAR_WEIGHT>
226.228

> <EXACT_MASS>
226.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.822117962165095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
2.389925829666667

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.285154400374239

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.109859112225939

> <JCHEM_PKA_STRONGEST_BASIC>
-5.548890486588076

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
57.89960000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyl gallate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
BUTYL gallic acid	Generator
N-Butyl gallate	MeSH

Chemical Formula

C₁₁H₁₄O₅

Average Mass

226.2280 Da

Monoisotopic Mass

226.08412 Da

IUPAC Name

butyl 3,4,5-trihydroxybenzoate

Traditional Name

butyl gallate

CAS Registry Number

Not Available

SMILES

CCCCOC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C11H14O5/c1-2-3-4-16-11(15)7-5-8(12)10(14)9(13)6-7/h5-6,12-14H,2-4H2,1H3

InChI Key

XOPOEBVTQYAOSV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alchornea glandulosa	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Galloyl 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.23	ALOGPS
logP	2.39	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	8.11	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	57.9 m³·mol⁻¹	ChemAxon
Polarizability	22.82 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

13505

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14128

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sannomiya M, Rodrigues CM, Oliveira GCA, Carvalho JCS, da Costa LS, Spadari CC, Ferreira MJP, Vilegas W, Ishida K: Galloylquinic acid derivatives from Byrsonima fagifolia leaf extract and potential antifungal activity. J Ethnopharmacol. 2022 Oct 28;297:115534. doi: 10.1016/j.jep.2022.115534. Epub 2022 Jul 14. [PubMed:35842178 ]
Wang X, Chen K, Zhang X, Hu Y, Wang Z, Yin F, Liu X, Zhang J, Qin L, Zhou D: Effect of carbon chain length on the hydrolysis and transport characteristics of alkyl gallates in rat intestine. Food Funct. 2021 Nov 1;12(21):10581-10588. doi: 10.1039/d1fo01732b. [PubMed:34614054 ]
Kim B, ParK JS, Choi HY, Kwak JH, Kim WG: Differential effects of alkyl gallates on quorum sensing in Pseudomonas aeruginosa. Sci Rep. 2019 May 23;9(1):7741. doi: 10.1038/s41598-019-44236-w. [PubMed:31123307 ]
Hirano A, Maruyama T, Shiraki K, Arakawa T, Kameda T: A study of the small-molecule system used to investigate the effect of arginine on antibody elution in hydrophobic charge-induction chromatography. Protein Expr Purif. 2017 Jan;129:44-52. doi: 10.1016/j.pep.2016.09.004. Epub 2016 Sep 10. [PubMed:27623150 ]
LOTUS database [Link]

Showing NP-Card for butyl gallate (NP0165631)

MOL for NP0165631 (butyl gallate)

3D MOL for NP0165631 (butyl gallate)

3D SDF for NP0165631 (butyl gallate)

3D-SDF for NP0165631 (butyl gallate)

PDB for NP0165631 (butyl gallate)

3D PDB for NP0165631 (butyl gallate)

SMILES for NP0165631 (butyl gallate)

INCHI for NP0165631 (butyl gallate)

Structure for NP0165631 (butyl gallate)

3D Structure for NP0165631 (butyl gallate)