Gallocatechin-(4alpha->8)-gallocatechin-(4alpha->8)-gallocatechin

Details

• Internal ID: 7d00b026-2d7b-4b43-b72c-e5cb35b1c6d0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: (2R,3S,4R)-2-(3,4,5-trihydroxyphenyl)-4-[(2R,3S)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-8-yl]-8-[(2R,3S,4S)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• SMILES (Canonical): C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=C(C(=CC(=C34)O)O)C5C(C(OC6=CC(=CC(=C56)O)O)C7=CC(=C(C(=C7)O)O)O)O)C8=CC(=C(C(=C8)O)O)O)O)O)O)C9=CC(=C(C(=C9)O)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=C1C(=CC(=C2[C@H]3[C@@H]([C@H](OC4=C(C(=CC(=C34)O)O)[C@H]5[C@@H]([C@H](OC6=CC(=CC(=C56)O)O)C7=CC(=C(C(=C7)O)O)O)O)C8=CC(=C(C(=C8)O)O)O)O)O)O)C9=CC(=C(C(=C9)O)O)O)O
• InChI: InChI=1S/C45H38O21/c46-15-7-18(48)30-29(8-15)64-42(13-3-24(54)37(60)25(55)4-13)39(62)34(30)32-20(50)11-21(51)33-35(40(63)43(66-45(32)33)14-5-26(56)38(61)27(57)6-14)31-19(49)10-17(47)16-9-28(58)41(65-44(16)31)12-1-22(52)36(59)23(53)2-12/h1-8,10-11,28,34-35,39-43,46-63H,9H2/t28-,34-,35+,39-,40-,41+,42+,43+/m0/s1
• InChI Key: NVTLDVSBUJGIAD-QHBXHTPSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₃₈O₂₁
• Molecular Weight: 914.80 g/mol
• Exact Mass: 914.19055822 g/mol
• Topological Polar Surface Area (TPSA): 392.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 3.56
• H-Bond Acceptor: 21
• H-Bond Donor: 18
• Rotatable Bonds: 5

Synonyms

• CHEBI:172852
• DTXSID601099470
• [Gallocatechin-(4alpha->8)]2-gallocatechin
• Gallocatechin(4a->8)gallocatechin(4a->8)gallocatechin
• (2R,2'R,2''R,3S,3'S,3''S,4S,4'R)-3,3',3'',4,4',4''-Hexahydro-2,2',2''-tris(3,4,5-trihydroxyphenyl)[4,8':4',8''-ter-2H-1-benzopyran]-3,3',3'',5,5',5'',7,7',7''-nonol
• (2R,3S,4R)-2-(3,4,5-trihydroxyphenyl)-4-[(2R,3S)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-8-yl]-8-[(2R,3S,4S)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• 4alpha,8':4'alpha,8''-Ter[(2R)-3beta,5,7-trihydroxy-3,4-dihydro-2alpha-(3,4,5-trihydroxyphenyl)-2H-1-benzopyran]
• 87402-90-2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8698	86.98%
Caco-2	-	0.8955	89.55%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.4793	47.93%
OATP2B1 inhibitior	-	0.7089	70.89%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7803	78.03%
P-glycoprotein inhibitior	+	0.6842	68.42%
P-glycoprotein substrate	-	0.7445	74.45%
CYP3A4 substrate	+	0.5728	57.28%
CYP2C9 substrate	-	0.5994	59.94%
CYP2D6 substrate	+	0.5264	52.64%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9155	91.55%
CYP2C8 inhibition	+	0.6697	66.97%
CYP inhibitory promiscuity	-	0.8625	86.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6139	61.39%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.8851	88.51%
Skin irritation	-	0.6044	60.44%
Skin corrosion	-	0.9317	93.17%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8651	86.51%
Micronuclear	+	0.7859	78.59%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.7665	76.65%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6861	68.61%
Acute Oral Toxicity (c)	IV	0.5696	56.96%
Estrogen receptor binding	+	0.7591	75.91%
Androgen receptor binding	+	0.7536	75.36%
Thyroid receptor binding	+	0.6062	60.62%
Glucocorticoid receptor binding	-	0.4678	46.78%
Aromatase binding	+	0.5305	53.05%
PPAR gamma	+	0.7308	73.08%
Honey bee toxicity	-	0.8191	81.91%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.6855	68.55%

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	99.66%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	97.82%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.55%	96.09%
CHEMBL1929	P47989	Xanthine dehydrogenase	93.14%	96.12%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.11%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.89%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.51%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	85.16%	94.73%
CHEMBL3194	P02766	Transthyretin	85.15%	90.71%
CHEMBL236	P41143	Delta opioid receptor	84.29%	99.35%
CHEMBL233	P35372	Mu opioid receptor	83.78%	97.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.33%	95.56%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.20%	96.37%
CHEMBL4208	P20618	Proteasome component C5	81.50%	90.00%
CHEMBL2535	P11166	Glucose transporter	80.68%	98.75%

Plants that contains it

• Aconitum violaceum
• Cistus × incanus
• Codonopsis pilosula
• Delphinium shawurense
• Fagraea gracilipes
• Garcinia xipshuanbannaensis
• Gutierrezia microcephala
• Helichrysum graveolens
• Iryanthera paraensis
• Lathyrus nissolia
• Leonurus persicus
• Magnolia sieboldii
• Peltogyne floribunda
• Ratibida mexicana
• Ribes nigrum

Cross-Links

• PubChem: 71664720
• NPASS: NPC137887
• LOTUS: LTS0245906
• wikiData: Q105281869