MiMeDB: Showing metabocard for digallate (MMDBc0054454)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:13:23 UTC

Update Date

2025-10-07 16:08:32 UTC

Metabolite ID

MMDBc0054454

Metabolite Identification

Common Name

digallate

Description

digallate is a flavonoid compound belonging to the class of polyphenols, specifically characterized as Theaflavin 3,3'-digallate (TF3). Its chemical structure features two galloyl groups esterified to a flavan-3-ol backbone, contributing to its unique biochemical properties. In various biological pathways, TF3 has been shown to act as a selective inhibitor of FBXO5, influencing cell cycle regulation (PMID:41045986 ). It suppresses metastasis and reduces insulin-like growth factor-1-induced cancer stemness and invasiveness in human melanoma cells, highlighting its potential in cancer therapy (PMID:40962244 ). Additionally, TF3 exhibits antidiabetic effects, induces apoptosis, and suppresses cancer growth, indicating its multifaceted role in cellular processes (PMID:40962244 ). The compound also interacts with cytochrome P450 enzymes and UDP-glucuronosyltransferases, affecting drug metabolism (PMID:40870734 ). Moreover, TF3 has been implicated in neuroprotection, preventing radiofrequency radiation-induced cognitive impairment by modulating GSK-3α/GRα/RORα/BMAL1 expression (PMID:40827634 ). Overall, digallate's diverse chemical interactions and biological effects underscore its significance in both pharmacology and toxicology.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241519182D          

 23 24  0  0  0  0            999 V2000
    2.1434   -2.8875    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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   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
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   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
    5.7158   -4.1250    0.0000 C   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
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   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
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  CHG  1   8  -1
M  END
> <DATABASE_ID>
MMDBc0054454

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)C1=CC(O)=C(O)C(OC(=O)C2=CC(O)=C([O-])C(O)=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O9/c15-7-2-6(3-8(16)11(7)18)14(22)23-10-4-5(13(20)21)1-9(17)12(10)19/h1-4,15-19H,(H,20,21)/p-1

> <INCHI_KEY>
COVFEVWNJUOYRL-UHFFFAOYSA-M

> <FORMULA>
C14H9O9

> <MOLECULAR_WEIGHT>
321.218

> <EXACT_MASS>
321.02520545

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.764445351809375

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(5-carboxy-2,3-dihydroxyphenoxy)carbonyl]-2,6-dihydroxybenzen-1-olate

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
2.424437528333333

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.030577152397965

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9120399911858206

> <JCHEM_PKA_STRONGEST_BASIC>
-4.7714917275338715

> <JCHEM_POLAR_SURFACE_AREA>
167.57999999999998

> <JCHEM_REFRACTIVITY>
85.57189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(5-carboxy-2,3-dihydroxyphenoxycarbonyl)-2,6-dihydroxybenzenolate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   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       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O-1
HETATM    9  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    4                                                            
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18                                                            
CONECT   20   17                                                            
CONECT   21   15   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

Synonyms

Value	Source
Digallic acid	Generator

Molecular Formula

C₁₄H₉O₉

Average Mass

321.218

Monoisotopic Mass

321.02520545

IUPAC Name

4-[(5-carboxy-2,3-dihydroxyphenoxy)carbonyl]-2,6-dihydroxybenzen-1-olate

Traditional Name

4-(5-carboxy-2,3-dihydroxyphenoxycarbonyl)-2,6-dihydroxybenzenolate

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC(O)=C(O)C(OC(=O)C2=CC(O)=C([O-])C(O)=C2)=C1

InChI Identifier

InChI=1S/C14H10O9/c15-7-2-6(3-8(16)11(7)18)14(22)23-10-4-5(13(20)21)1-9(17)12(10)19/h1-4,15-19H,(H,20,21)/p-1

InChI Key

COVFEVWNJUOYRL-UHFFFAOYSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depside backbone
Gallic acid or derivatives
M-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Hydroxybenzoic acid
Benzoate ester
Phenol ester
Benzoic acid or derivatives
Benzoic acid
Resorcinol
Phenoxy compound
Catechol
Benzoyl
Phenoxide
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Organic anion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

trihydroxybenzoate (CHEBI:17866 )
a small molecule (CPD-1118 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
logP	2.03	ALOGPS
logP	2.42	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.91	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	167.58 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	85.57 m³·mol⁻¹	ChemAxon
Polarizability	28.76 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	111.5
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	97.4
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	282.6
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	416.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	474.7
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	247.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1172.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	414.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	624.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	156.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	258.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	144.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	74.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	509.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	616.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	69.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	306.1
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1228.1
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	686.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	digallate_TMS_1	C[Si](C)(C)OC(=O)C1=CC(O)=C(O)C(OC(=O)C2=CC(O)=C([O-])C(O)=C2)=C1	standard non polar	2025-10-24	1676.66
Gas Chromatography	digallate_TMS_2	C[Si](C)(C)OC1=CC(C(=O)O)=CC(OC(=O)C2=CC(O)=C([O-])C(O)=C2)=C1O	standard non polar	2025-10-24	1991.67
Gas Chromatography	digallate_TMS_3	C[Si](C)(C)OC1=C(O)C=C(C(=O)O)C=C1OC(=O)C1=CC(O)=C([O-])C(O)=C1	standard non polar	2025-10-24	2246.08
Gas Chromatography	digallate_TMS_4	C[Si](C)(C)OC1=CC(C(=O)OC2=CC(C(=O)O)=CC(O)=C2O)=CC(O)=C1[O-]	standard non polar	2025-10-24	2180.76
Gas Chromatography	digallate_TMS_5	C[Si](C)(C)OC(=O)C1=CC(OC(=O)C2=CC(O)=C([O-])C(O)=C2)=C(O)C(O[Si](C)(C)C)=C1	standard non polar	2025-10-24	2046.82
Gas Chromatography	digallate_TMS_6	C[Si](C)(C)OC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(OC(=O)C2=CC(O)=C([O-])C(O)=C2)=C1	standard non polar	2025-10-24	2021.52
Gas Chromatography	digallate_TMS_7	C[Si](C)(C)OC(=O)C1=CC(O)=C(O)C(OC(=O)C2=CC(O)=C([O-])C(O[Si](C)(C)C)=C2)=C1	standard non polar	2025-10-24	1627.54
Gas Chromatography	digallate_TMS_8	C[Si](C)(C)OC1=CC(C(=O)OC2=CC(C(=O)O)=CC(O[Si](C)(C)C)=C2O)=CC(O)=C1[O-]	standard non polar	2025-10-24	2327.78
Gas Chromatography	digallate_TMS_9	C[Si](C)(C)OC1=CC(C(=O)O)=CC(OC(=O)C2=CC(O)=C([O-])C(O)=C2)=C1O[Si](C)(C)C	standard non polar	2025-10-24	2271.03
Gas Chromatography	digallate_TMS_10	C[Si](C)(C)OC1=CC(C(=O)OC2=CC(C(=O)O)=CC(O)=C2O[Si](C)(C)C)=CC(O)=C1[O-]	standard non polar	2025-10-24	2201.78
Gas Chromatography	digallate_TMS_11	C[Si](C)(C)OC1=CC(C(=O)OC2=CC(C(=O)O)=CC(O)=C2O)=CC(O[Si](C)(C)C)=C1[O-]	standard non polar	2025-10-24	2794.32
Gas Chromatography	digallate_TMS_12	C[Si](C)(C)OC(=O)C1=CC(OC(=O)C2=CC(O)=C([O-])C(O[Si](C)(C)C)=C2)=C(O)C(O[Si](C)(C)C)=C1	standard non polar	2025-10-24	1600.27
Gas Chromatography	digallate_TMS_13	C[Si](C)(C)OC(=O)C1=CC(OC(=O)C2=CC(O)=C([O-])C(O)=C2)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	standard non polar	2025-10-24	2032.25
Gas Chromatography	digallate_TMS_14	C[Si](C)(C)OC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(OC(=O)C2=CC(O)=C([O-])C(O[Si](C)(C)C)=C2)=C1	standard non polar	2025-10-24	2291.53
Gas Chromatography	digallate_TMS_15	C[Si](C)(C)OC(=O)C1=CC(O)=C(O)C(OC(=O)C2=CC(O[Si](C)(C)C)=C([O-])C(O[Si](C)(C)C)=C2)=C1	standard non polar	2025-10-24	1992.56
Gas Chromatography	digallate_TMS_16	C[Si](C)(C)OC1=CC(C(=O)OC2=CC(C(=O)O)=CC(O[Si](C)(C)C)=C2O[Si](C)(C)C)=CC(O)=C1[O-]	standard non polar	2025-10-24	1983.46
Gas Chromatography	digallate_TMS_17	C[Si](C)(C)OC1=CC(C(=O)OC2=CC(C(=O)O)=CC(O[Si](C)(C)C)=C2O)=CC(O[Si](C)(C)C)=C1[O-]	standard non polar	2025-10-24	2144.75
Gas Chromatography	digallate_TMS_18	C[Si](C)(C)OC1=CC(C(=O)OC2=CC(C(=O)O)=CC(O)=C2O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1[O-]	standard non polar	2025-10-24	3136.85
Gas Chromatography	digallate_TMS_19	C[Si](C)(C)OC(=O)C1=CC(OC(=O)C2=CC(O[Si](C)(C)C)=C([O-])C(O[Si](C)(C)C)=C2)=C(O)C(O[Si](C)(C)C)=C1	standard non polar	2025-10-24	2892.0
Gas Chromatography	digallate_TMS_20	C[Si](C)(C)OC(=O)C1=CC(OC(=O)C2=CC(O)=C([O-])C(O[Si](C)(C)C)=C2)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	standard non polar	2025-10-24	2508.44
Gas Chromatography	digallate_TMS_21	C[Si](C)(C)OC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(OC(=O)C2=CC(O[Si](C)(C)C)=C([O-])C(O[Si](C)(C)C)=C2)=C1	standard non polar	2025-10-24	2548.95
Gas Chromatography	digallate_TMS_22	C[Si](C)(C)OC1=CC(C(=O)OC2=CC(C(=O)O)=CC(O[Si](C)(C)C)=C2O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1[O-]	standard non polar	2025-10-24	2326.86
Gas Chromatography	digallate_TMS_23	C[Si](C)(C)OC(=O)C1=CC(OC(=O)C2=CC(O[Si](C)(C)C)=C([O-])C(O[Si](C)(C)C)=C2)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	standard non polar	2025-10-24	1601.54
Gas Chromatography	digallate_TMS_1	C[Si](C)(C)OC(=O)C1=CC(O)=C(O)C(OC(=O)C2=CC(O)=C([O-])C(O)=C2)=C1	standard polar	2025-10-24	2699.47
Gas Chromatography	digallate_TMS_2	C[Si](C)(C)OC1=CC(C(=O)O)=CC(OC(=O)C2=CC(O)=C([O-])C(O)=C2)=C1O	standard polar	2025-10-24	2096.95
Gas Chromatography	digallate_TMS_3	C[Si](C)(C)OC1=C(O)C=C(C(=O)O)C=C1OC(=O)C1=CC(O)=C([O-])C(O)=C1	standard polar	2025-10-24	2698.65
Gas Chromatography	digallate_TMS_4	C[Si](C)(C)OC1=CC(C(=O)OC2=CC(C(=O)O)=CC(O)=C2O)=CC(O)=C1[O-]	standard polar	2025-10-24	2159.84
Gas Chromatography	digallate_TMS_5	C[Si](C)(C)OC(=O)C1=CC(OC(=O)C2=CC(O)=C([O-])C(O)=C2)=C(O)C(O[Si](C)(C)C)=C1	standard polar	2025-10-24	2364.97
Gas Chromatography	digallate_TMS_6	C[Si](C)(C)OC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(OC(=O)C2=CC(O)=C([O-])C(O)=C2)=C1	standard polar	2025-10-24	1332.47
Gas Chromatography	digallate_TMS_7	C[Si](C)(C)OC(=O)C1=CC(O)=C(O)C(OC(=O)C2=CC(O)=C([O-])C(O[Si](C)(C)C)=C2)=C1	standard polar	2025-10-24	1362.68
Gas Chromatography	digallate_TMS_8	C[Si](C)(C)OC1=CC(C(=O)OC2=CC(C(=O)O)=CC(O[Si](C)(C)C)=C2O)=CC(O)=C1[O-]	standard polar	2025-10-24	2339.87
Gas Chromatography	digallate_TMS_9	C[Si](C)(C)OC1=CC(C(=O)O)=CC(OC(=O)C2=CC(O)=C([O-])C(O)=C2)=C1O[Si](C)(C)C	standard polar	2025-10-24	1625.3
Gas Chromatography	digallate_TMS_10	C[Si](C)(C)OC1=CC(C(=O)OC2=CC(C(=O)O)=CC(O)=C2O[Si](C)(C)C)=CC(O)=C1[O-]	standard polar	2025-10-24	2819.63
Gas Chromatography	digallate_TMS_11	C[Si](C)(C)OC1=CC(C(=O)OC2=CC(C(=O)O)=CC(O)=C2O)=CC(O[Si](C)(C)C)=C1[O-]	standard polar	2025-10-24	2056.75
Gas Chromatography	digallate_TMS_12	C[Si](C)(C)OC(=O)C1=CC(OC(=O)C2=CC(O)=C([O-])C(O[Si](C)(C)C)=C2)=C(O)C(O[Si](C)(C)C)=C1	standard polar	2025-10-24	3337.76
Gas Chromatography	digallate_TMS_13	C[Si](C)(C)OC(=O)C1=CC(OC(=O)C2=CC(O)=C([O-])C(O)=C2)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	standard polar	2025-10-24	2080.46
Gas Chromatography	digallate_TMS_14	C[Si](C)(C)OC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(OC(=O)C2=CC(O)=C([O-])C(O[Si](C)(C)C)=C2)=C1	standard polar	2025-10-24	1732.02
Gas Chromatography	digallate_TMS_15	C[Si](C)(C)OC(=O)C1=CC(O)=C(O)C(OC(=O)C2=CC(O[Si](C)(C)C)=C([O-])C(O[Si](C)(C)C)=C2)=C1	standard polar	2025-10-24	2597.5
Gas Chromatography	digallate_TMS_16	C[Si](C)(C)OC1=CC(C(=O)OC2=CC(C(=O)O)=CC(O[Si](C)(C)C)=C2O[Si](C)(C)C)=CC(O)=C1[O-]	standard polar	2025-10-24	2728.23
Gas Chromatography	digallate_TMS_17	C[Si](C)(C)OC1=CC(C(=O)OC2=CC(C(=O)O)=CC(O[Si](C)(C)C)=C2O)=CC(O[Si](C)(C)C)=C1[O-]	standard polar	2025-10-24	2592.48
Gas Chromatography	digallate_TMS_18	C[Si](C)(C)OC1=CC(C(=O)OC2=CC(C(=O)O)=CC(O)=C2O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1[O-]	standard polar	2025-10-24	3125.26
Gas Chromatography	digallate_TMS_19	C[Si](C)(C)OC(=O)C1=CC(OC(=O)C2=CC(O[Si](C)(C)C)=C([O-])C(O[Si](C)(C)C)=C2)=C(O)C(O[Si](C)(C)C)=C1	standard polar	2025-10-24	2101.21
Gas Chromatography	digallate_TMS_20	C[Si](C)(C)OC(=O)C1=CC(OC(=O)C2=CC(O)=C([O-])C(O[Si](C)(C)C)=C2)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	standard polar	2025-10-24	2400.17
Gas Chromatography	digallate_TMS_21	C[Si](C)(C)OC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(OC(=O)C2=CC(O[Si](C)(C)C)=C([O-])C(O[Si](C)(C)C)=C2)=C1	standard polar	2025-10-24	2646.75
Gas Chromatography	digallate_TMS_22	C[Si](C)(C)OC1=CC(C(=O)OC2=CC(C(=O)O)=CC(O[Si](C)(C)C)=C2O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1[O-]	standard polar	2025-10-24	2726.86
Gas Chromatography	digallate_TMS_23	C[Si](C)(C)OC(=O)C1=CC(OC(=O)C2=CC(O[Si](C)(C)C)=C([O-])C(O[Si](C)(C)C)=C2)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	standard polar	2025-10-24	2103.16

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1
Bacteria/Eubacteria	Firmicutes	1	Human

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Digallate

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

17866

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for digallate (MMDBc0054454)

MOL for #<Metabolite:0x00007fade8333338>

3D MOL for #<Metabolite:0x00007fade8333338>

3D SDF for #<Metabolite:0x00007fade8333338>

3D-SDF for #<Metabolite:0x00007fade8333338>

PDB for #<Metabolite:0x00007fade8333338>

3D PDB for #<Metabolite:0x00007fade8333338>

SMILES for #<Metabolite:0x00007fade8333338>

INCHI for #<Metabolite:0x00007fade8333338>

Structure for #<Metabolite:0x00007fade8333338>

3D Structure for #<Metabolite:0x00007fade8333338>