Gallotannin

Details

• Internal ID: f5090e93-7f86-4860-81e3-568611464fb3
• Taxonomy: Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
• IUPAC Name: [2,3-dihydroxy-5-[[(2R,3R,4S,5R,6S)-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+/m1/s1
• InChI Key: LRBQNJMCXXYXIU-PPKXGCFTSA-N
• Popularity: 31,591 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

Synonyms

• 1401-55-4
• Gallotannin
• Glycerite
• 5424-20-4
• Gallotannic acid
• Chinese gallotannin
• MFCD00066397
• MLS001335996
• CHEBI:81066
• EINECS 226-562-9
• [2,3-dihydroxy-5-[[(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoyl]oxy]oxan-2-yl]methoxycarbonyl]phenyl] 3,4,5-trihydroxybenzoate
• SMR000857330
• C76H52O46
• DSSTox_CID_6076
• DSSTox_RID_78006
• DSSTox_GSID_26076
• Taninos
• Tannins
• [2,3-Dihydroxy-5-[[3,4,5,6-tetrakis[[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoyl]oxy]oxan-2-yl]methoxycarbonyl]phenyl] 3,4,5-trihydroxybenzoate
• Tannicum acidum
• Acide tannique
• FEMA No. 3042
• Acid, tannic
• d'Acide tannique
• Tannin from mimosa
• Tannin from chestnut
• Tannin from quebracho
• Liquidambar styraciflua
• Caswell No. 819
• beta-D-Glucose pentakis(3,4-dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)benzoate)
• BETA-D-GLUCOSE PENTAKIS[3,4-DIHYDROXY-5-[(3,4,5-TRIHYDROXYBENZOYL)OXY]BENZOATE]
• Tannic acid and tannins
• Acacia mollissima tannin
• TNA (CHRIS Code)
• CAS-1401-55-4
• Acide tannique [French]
• Schinopsis lorentzii tannin
• d'Acide tannique [French]
• Castanea sativa Mill tannin
• UNII-28F9E0DJY6
• Tannic acid (Quercus spp.)
• CCRIS 571
• HSDB 831
• UNII-2711I21VE5
• tannic-acid
• EINECS 215-753-2
• NSC656273
• EPA Pesticide Chemical Code 078502
• NSC 656273
• NSC-656273
• NSC-758670
• Tannic acid (hydrolyzable gallotannins)
• C76-H52-O46
• NCGC00095101-01
• TANNICACID
• Tannin (Tannic acid)
• Asian holly oak nutgall
• Tannic acid, ACS reagent
• D0R4WJ
• Tannic acid, technical grade
• MLS001335995
• SCHEMBL409692
• Tannic acid, SAJ first grade
• CHEMBL506247
• GTPL4319
• BDBM60986
• DTXSID00892987
• Tannic acid, puriss., 95.0%
• cid_16129778
• LRBQNJMCXXYXIU-PPKXGCFTSA-N
• Tox21_111422
• Tox21_300079
• BDBM50442879
• s3951
• AKOS015951319
• Tannic acid, Vetec(TM) reagent grade
• CCG-270692
• NCGC00186054-01
• NCGC00186054-02
• NCGC00253925-01
• Tannic acid, tested according to Ph.Eur.
• C17409
• Tannic acid, Source: Chinese natural gall nuts
• A901485
• Q427956
• Q-201780
• Tannic acid, puriss., meets analytical specification of USP, powder
• Tannic acid, United States Pharmacopeia (USP) Reference Standard
• .Beta.-D-glucopyranose, pentakis[3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoate]
• beta-D-Glucopyranose pentakis[3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoate]
• (2R,3R,4S,5R,6S)-4,5,6-tris({3,4-dihydroxy-5-[(3,4,5-trihydroxyphenyl)carbonyloxy]phenyl}carbonyloxy)-2-[({3,4-dihydroxy-5-[(3,4,5-trihydroxyphenyl)carbonyloxy]phenyl}carbonyloxy)methyl]oxan-3-yl 3,4-dihydroxy-5-[(3,4,5-trihydroxyphenyl)carbonyloxy]benzoate
• (2S,3R,4S,5R,6R)-6-(((3,4-Dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)benzoyl)oxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrakis(3,4-dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)benzoate)
• [2,3-dihydroxy-5-[[(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxy-benzoyl]oxy]tetrahydropyran-2-yl]methoxycarbonyl]phenyl] 3,4,5-trihydroxybenzoate
• [2,3-dihydroxy-5-[[(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoyl]oxy]oxan-2-yl]methoxycarbonyl]phenyl]3,4,5-trihydroxybenzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL205	P00918	Carbonic anhydrase II	32800 nM	Ki	PMID: 21669522
CHEMBL3025	P23280	Carbonic anhydrase VI	17800 nM	Ki	PMID: 21669522
CHEMBL3356	P05177	Cytochrome P450 1A2	919 nM	IC50	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	4607.4 nM	IC50	via CMAUP
CHEMBL402	P04035	HMG-CoA reductase	3127 nM	IC50	via CMAUP
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	100 nM; 100 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL3385	P27361	MAP kinase ERK1	4052 nM	IC50	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	185 nM	IC50	via CMAUP
CHEMBL260	Q16539	MAP kinase p38 alpha	375 nM	IC50	via CMAUP
CHEMBL1827	O76074	Phosphodiesterase 5A	4703 nM	IC50	via CMAUP
CHEMBL1697668	Q9Y6L6	Solute carrier organic anion transporter family member 1B1	2630.27 nM	IC50	PMID: 23571415
CHEMBL1743121	Q9NPD5	Solute carrier organic anion transporter family member 1B3	4168.69 nM	IC50	PMID: 23571415
CHEMBL1835	P24557	Thromboxane-A synthase	325 nM; 325 nM	IC50; IC50	via Super-PRED; via CMAUP
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	22 nM	IC50	via CMAUP
CHEMBL258	P06239	Tyrosine-protein kinase LCK	79 nM	IC50	via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	5011.9 nM	Potency	via CMAUP

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

• Acacia pruinosa
• Aegilops geniculata
• Azadirachta indica
• Cycas beddomei
• Humulus scandens
• Iodes cirrhosa
• Lespedeza davidii
• Phyllanthus emblica
• Sorghum bicolor
• Syzygium samarangense
• Terminalia chebula
• Trollius chinensis
• Zingiber officinale

Cross-Links

• PubChem: 16129778
• NPASS: NPC149300
• ChEMBL: CHEMBL506247