Acide tannique [French]

Details

• Internal ID: 5a39d137-adf0-4cc9-8f8e-1d9ca947f4f3
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: [2,3-dihydroxy-5-[[(2S,3S,4R,5S,6R)-3,4,5,6-tetrakis[[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoyl]oxy]oxan-2-yl]methoxycarbonyl]phenyl] 3,4,5-trihydroxybenzoate
• SMILES (Canonical): C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O)OCC3C(C(C(C(O3)OC(=O)C4=CC(=C(C(=C4)OC(=O)C5=CC(=C(C(=C5)O)O)O)O)O)OC(=O)C6=CC(=C(C(=C6)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)O)OC(=O)C8=CC(=C(C(=C8)OC(=O)C9=CC(=C(C(=C9)O)O)O)O)O)OC(=O)C1=CC(=C(C(=C1)OC(=O)C1=CC(=C(C(=C1)O)O)O)O)O
• SMILES (Isomeric): C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O)OC[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)OC(=O)C4=CC(=C(C(=C4)OC(=O)C5=CC(=C(C(=C5)O)O)O)O)O)OC(=O)C6=CC(=C(C(=C6)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)O)OC(=O)C8=CC(=C(C(=C8)OC(=O)C9=CC(=C(C(=C9)O)O)O)O)O)OC(=O)C1=CC(=C(C(=C1)OC(=O)C1=CC(=C(C(=C1)O)O)O)O)O
• InChI: InChI=1S/C76H52O46/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26/h1-20,52,63-65,76-101H,21H2/t52-,63-,64+,65-,76+/m0/s1
• InChI Key: LRBQNJMCXXYXIU-QWKBTXIPSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇₆H₅₂O₄₆
• Molecular Weight: 1701.20 g/mol
• Exact Mass: 1700.1729741 g/mol
• Topological Polar Surface Area (TPSA): 778.00 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 4.84
• H-Bond Acceptor: 46
• H-Bond Donor: 25
• Rotatable Bonds: 21

Synonyms

• Tannic acid [USP:JAN]
• Gallotannin
• Glycerite
• Tannins
• Acide tannique
• Gallotannic acid
• Acid, tannic
• d'Acide tannique
• Tannin from mimosa
• Tannin from chestnut
• Tannin from quebracho
• Caswell No. 819
• Liquidambar styraciflua
• Acacia mollissima tannin
• Tannic acid and tannins
• Acide tannique [French]
• Schinopsis lorentzii tannin
• d'Acide tannique [French]
• Castanea sativa Mill tannin
• Tannic acid (Quercus spp.)
• UNII-28F9E0DJY6
• Taninos
• CCRIS 571
• Chestnut tannin
• Mimosa tannin
• FEMA No. 3042
• HSDB 831
• Quebracho tannin
• EINECS 215-753-2
• EPA Pesticide Chemical Code 078502
• NSC 656273
• TNA (CHRIS Code)
• 28F9E0DJY6
• UNII-2711I21VE5
• C76H52O46
• Tannic acid (hydrolyzable gallotannins)
• SCHEMBL17432880

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5975	59.75%
Caco-2	-	0.8610	86.10%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7179	71.79%
OATP2B1 inhibitior	-	0.5736	57.36%
OATP1B1 inhibitior	-	0.7740	77.40%
OATP1B3 inhibitior	-	0.5698	56.98%
MATE1 inhibitior	+	0.7000	70.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.7296	72.96%
P-glycoprotein inhibitior	+	0.7461	74.61%
P-glycoprotein substrate	-	0.8951	89.51%
CYP3A4 substrate	+	0.5459	54.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8473	84.73%
CYP3A4 inhibition	-	0.8325	83.25%
CYP2C9 inhibition	-	0.7629	76.29%
CYP2C19 inhibition	-	0.8866	88.66%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.9107	91.07%
CYP2C8 inhibition	+	0.5934	59.34%
CYP inhibitory promiscuity	-	0.7781	77.81%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7506	75.06%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.8950	89.50%
Skin irritation	-	0.8336	83.36%
Skin corrosion	-	0.9589	95.89%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7255	72.55%
Micronuclear	+	0.6966	69.66%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8119	81.19%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9389	93.89%
Acute Oral Toxicity (c)	III	0.8042	80.42%
Estrogen receptor binding	+	0.7192	71.92%
Androgen receptor binding	+	0.7315	73.15%
Thyroid receptor binding	+	0.5646	56.46%
Glucocorticoid receptor binding	-	0.4672	46.72%
Aromatase binding	+	0.5894	58.94%
PPAR gamma	+	0.7264	72.64%
Honey bee toxicity	-	0.7705	77.05%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5950	59.50%
Fish aquatic toxicity	+	0.9022	90.22%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	100 nM	Potency	via Super-PRED
CHEMBL1835	P24557	Thromboxane-A synthase	325 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.08%	91.11%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	97.17%	83.00%
CHEMBL3194	P02766	Transthyretin	93.50%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.33%	96.09%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.41%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.27%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.07%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.53%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.86%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.94%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	85.86%	94.73%
CHEMBL5255	O00206	Toll-like receptor 4	85.56%	92.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	84.82%	95.17%
CHEMBL4208	P20618	Proteasome component C5	83.23%	90.00%
CHEMBL2581	P07339	Cathepsin D	80.47%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.08%	92.62%

Plants that contains it

• Albizia julibrissin
• Gleditsia sinensis
• Grona styracifolia
• Hibiscus syriacus
• Ilex pubescens
• Persicaria bistorta
• Pteris multifida
• Sambucus williamsii
• Sargentodoxa cuneata
• Selaginella tamariscina
• Swertia hickinii
• Thalictrum foliolosum
• Trachycarpus fortunei

Cross-Links

• PubChem: 16133892
• NPASS: NPC113961