Digallic acid

Details

• Internal ID: bf7285ef-62c9-4de6-ac3e-d06b4f0d4518
• Taxonomy: Phenylpropanoids and polyketides > Depsides and depsidones
• IUPAC Name: 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoic acid
• SMILES (Canonical): C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O)O
• SMILES (Isomeric): C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O)O
• InChI: 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)
• InChI Key: COVFEVWNJUOYRL-UHFFFAOYSA-N
• Popularity: 93 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₀O₉
• Molecular Weight: 322.22 g/mol
• Exact Mass: 322.03248189 g/mol
• Topological Polar Surface Area (TPSA): 165.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.13
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

• 536-08-3
• m-Digallic acid
• Gallic acid 3-monogallate
• m-Galloylgallic acid
• m-Galloyl gallic acid
• 3-Galloyl gallic acid
• Gallic acid, 3-gallate
• 3,4-Dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)benzoic acid
• NSC 59263
• NSC-59263
• CHEMBL366356
• UNII-404KO0584X
• CHEBI:30814
• gallic acid 5,6-dihydroxy-3-carboxyphenyl ester
• NSC59263
• 5,6-Dihydroxy-3-carboxyphenyl ester of gallic acid
• EINECS 208-624-7
• 404KO0584X
• BRN 2177723
• 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoic acid
• 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoic acid
• 3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoic acid
• 3-10-00-02086 (Beilstein Handbook Reference)
• Benzoic acid, 3,4-dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)-
• Digallussaure
• Benzoic acid, 3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]-
• 3-galloyloxy-4,5-dihydroxy-benzoic acid
• DIGALLIC ACID, M-
• DIGALLIC ACID, META
• DIGALLIC ACID [MI]
• NCIOpen2_007819
• SCHEMBL39415
• DTXSID50871747
• BCP32287
• BDBM50056937
• AKOS040751568
• DISCONTINUED. Please see D445080
• 4,5-DIHYDROXYBENZOIC ACID MONOGALLATE
• FT-0666845
• C01572
• Q4140499
• 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxy-benzoic acid
• Benzoic acid,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]-
• m-Digallic acid;Gallic acid 3-monogallate;m-Galloylgallic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8395	83.95%
Caco-2	-	0.8360	83.60%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7505	75.05%
OATP2B1 inhibitior	+	0.5751	57.51%
OATP1B1 inhibitior	+	0.9039	90.39%
OATP1B3 inhibitior	+	0.8776	87.76%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8848	88.48%
P-glycoprotein inhibitior	-	0.9390	93.90%
P-glycoprotein substrate	-	0.9735	97.35%
CYP3A4 substrate	-	0.7128	71.28%
CYP2C9 substrate	-	0.7828	78.28%
CYP2D6 substrate	-	0.8795	87.95%
CYP3A4 inhibition	-	0.8888	88.88%
CYP2C9 inhibition	-	0.7862	78.62%
CYP2C19 inhibition	-	0.9570	95.70%
CYP2D6 inhibition	-	0.9534	95.34%
CYP1A2 inhibition	-	0.8010	80.10%
CYP2C8 inhibition	-	0.5607	56.07%
CYP inhibitory promiscuity	-	0.8663	86.63%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7997	79.97%
Carcinogenicity (trinary)	Non-required	0.6780	67.80%
Eye corrosion	-	0.9930	99.30%
Eye irritation	+	0.9642	96.42%
Skin irritation	-	0.5441	54.41%
Skin corrosion	-	0.9097	90.97%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6611	66.11%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.5438	54.38%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7730	77.30%
Acute Oral Toxicity (c)	III	0.8285	82.85%
Estrogen receptor binding	+	0.5821	58.21%
Androgen receptor binding	+	0.7234	72.34%
Thyroid receptor binding	-	0.6121	61.21%
Glucocorticoid receptor binding	+	0.5978	59.78%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.5826	58.26%
Honey bee toxicity	-	0.8304	83.04%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7650	76.50%
Fish aquatic toxicity	+	0.9902	99.02%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1828	P09884	DNA polymerase alpha subunit	830 nM; 830 nM	Ki; Ki	PMID: 1705574; via Super-PRED
CHEMBL2392	P06746	DNA polymerase beta	390 nM; 390 nM	Ki; Ki	PMID: 1705574; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3194	P02766	Transthyretin	97.32%	90.71%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.64%	91.11%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	88.22%	94.42%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.71%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.48%	99.17%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	83.45%	81.11%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.83%	95.50%
CHEMBL1255126	O15151	Protein Mdm4	82.81%	90.20%
CHEMBL1811	P34995	Prostanoid EP1 receptor	82.79%	95.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.41%	96.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.26%	97.21%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	80.65%	87.67%

Plants that contains it

• Acer rubrum
• Ampelopsis japonica
• Bombax ceiba
• Brucea javanica
• Centaurea virgata subsp. squarrosa
• Humulus scandens
• Litsea rotundifolia
• Mangifera indica
• Paeonia lactiflora
• Phyllanthus emblica
• Pistacia lentiscus
• Platycarya strobilacea
• Quercus infectoria
• Rhus chinensis
• Rhus coriaria
• Rhus potaninii
• Rhus punjabensis
• Vachellia nilotica
• Vachellia nilotica subsp. tomentosa

Cross-Links

• PubChem: 341
• NPASS: NPC134975
• ChEMBL: CHEMBL366356
• LOTUS: LTS0019534
• wikiData: Q4140499