Gallagic acid

Details

• Internal ID: a89bdaf8-45c8-4175-a570-f84217ab5e07
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: 2-[12-(6-carboxy-2,3,4-trihydroxyphenyl)-6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),4(16),5,7,11(15),12-hexaen-5-yl]-3,4,5-trihydroxybenzoic acid
• SMILES (Canonical): C1=C(C(=C(C(=C1O)O)O)C2=C(C(=C3C4=C2C(=O)OC5=C(C(=C(C(=C45)C(=O)O3)C6=C(C(=C(C=C6C(=O)O)O)O)O)O)O)O)O)C(=O)O
• SMILES (Isomeric): C1=C(C(=C(C(=C1O)O)O)C2=C(C(=C3C4=C2C(=O)OC5=C(C(=C(C(=C45)C(=O)O3)C6=C(C(=C(C=C6C(=O)O)O)O)O)O)O)O)O)C(=O)O
• InChI: InChI=1S/C28H14O18/c29-5-1-3(25(39)40)7(17(33)15(5)31)9-13-11-12-14(28(44)46-23(11)21(37)19(9)35)10(20(36)22(38)24(12)45-27(13)43)8-4(26(41)42)2-6(30)16(32)18(8)34/h1-2,29-38H,(H,39,40)(H,41,42)
• InChI Key: ZASJRRFAYSNSHU-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₁₄O₁₈
• Molecular Weight: 638.40 g/mol
• Exact Mass: 638.01801359 g/mol
• Topological Polar Surface Area (TPSA): 330.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 2.28
• H-Bond Acceptor: 16
• H-Bond Donor: 12
• Rotatable Bonds: 4

Synonyms

• TSN85LPS4R
• 65995-62-2
• 2-(12-(6-Carboxy-2,3,4-trihydroxyphenyl)-6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo(6.6.2.04,16.011,15)hexadeca-1(14),4(16),5,7,11(15),12-hexaen-5-yl)-3,4,5-trihydroxybenzoic acid
• Benzoic acid, 2,2'-(5,10-dihydro-2,3,7,8-tetrahydroxy-5,10-dioxo(1)benzopyrano(5,4,3-cde)(1)benzopyran-1,6-diyl)bis(3,4,5-trihydroxy-, stereoisomer
• Stereoisomer of 2,2'-(5,10-dihydro-2,3,7,8-tetrahydroxy-5,10-dioxo(1)benzopyrano(5,4,3-cde)(1)benzopyran-1,6-diyl)bis(3,4,5-trihydroxybenzoic acid)
• UNII-TSN85LPS4R
• DTXSID80563643
• FT-0777848
• Q5518842

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7231	72.31%
Caco-2	-	0.8849	88.49%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6370	63.70%
OATP2B1 inhibitior	+	0.5831	58.31%
OATP1B1 inhibitior	+	0.8768	87.68%
OATP1B3 inhibitior	+	0.9636	96.36%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5173	51.73%
P-glycoprotein inhibitior	-	0.6159	61.59%
P-glycoprotein substrate	-	0.9549	95.49%
CYP3A4 substrate	-	0.6893	68.93%
CYP2C9 substrate	-	0.8114	81.14%
CYP2D6 substrate	-	0.8805	88.05%
CYP3A4 inhibition	-	0.7079	70.79%
CYP2C9 inhibition	-	0.6597	65.97%
CYP2C19 inhibition	-	0.9059	90.59%
CYP2D6 inhibition	-	0.9697	96.97%
CYP1A2 inhibition	-	0.7757	77.57%
CYP2C8 inhibition	-	0.6423	64.23%
CYP inhibitory promiscuity	-	0.8851	88.51%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7391	73.91%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.5401	54.01%
Skin irritation	-	0.5243	52.43%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6782	67.82%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.8537	85.37%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7770	77.70%
Acute Oral Toxicity (c)	II	0.6454	64.54%
Estrogen receptor binding	+	0.7641	76.41%
Androgen receptor binding	+	0.7106	71.06%
Thyroid receptor binding	-	0.5200	52.00%
Glucocorticoid receptor binding	+	0.6657	66.57%
Aromatase binding	-	0.4936	49.36%
PPAR gamma	+	0.8093	80.93%
Honey bee toxicity	-	0.9645	96.45%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.9534	95.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.93%	91.11%
CHEMBL3194	P02766	Transthyretin	95.09%	90.71%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	93.84%	94.42%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	93.38%	81.11%
CHEMBL1811	P34995	Prostanoid EP1 receptor	91.69%	95.71%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	90.96%	87.67%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.93%	94.45%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	89.20%	89.34%
CHEMBL2581	P07339	Cathepsin D	88.42%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.08%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.46%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.42%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.31%	89.00%
CHEMBL5905	Q04828	Aldo-keto reductase family 1 member C1	85.54%	91.79%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	85.52%	80.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.09%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.10%	95.64%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.86%	85.11%

Plants that contains it

• Aglaia elaeagnoidea
• Aristolochia littoralis
• Astragalus gummifer
• Cardiospermum halicacabum
• Centaurea nigrescens
• Cirsium japonicum
• Combretum indicum
• Coreopsis fasciculata
• Crepis foetida
• Crinum viviparum
• Cuphea carthagenensis
• Dioscoreophyllum cumminsii
• Dorstenia lindeniana
• Erigeron canadensis
• Euphorbia segetalis
• Garcinia celebica
• Ozoroa insignis
• Parastrephia lepidophylla
• Penstemon secundiflorus
• Phedimus kamtschaticus
• Phlogacanthus thyrsiformis
• Phytolacca acinosa
• Piper arboreum
• Pouzolzia occidentalis
• Punica granatum
• Ruta microcarpa
• Selinum carvifolium
• Sidastrum multiflorum
• Syncolostemon parviflorus
• Thuja plicata
• Triglochin maritima
• Urtica triangularis
• Zanthoxylum schreberi

Cross-Links

• PubChem: 14754405
• NPASS: NPC24858
• LOTUS: LTS0205370
• wikiData: Q5518842