[(5R)-4,5-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-4-[(3,4,5-trihydroxybenzoyl)oxymethyl]oxolan-2-yl]methyl 3,4,5-trihydroxybenzoate

Details

• Internal ID: 29f8833d-2815-47b7-94c9-c18344f0fb30
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Hydroxybenzoic acid derivatives > Gallic acid and derivatives > Galloyl esters
• IUPAC Name: [(5R)-4,5-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-4-[(3,4,5-trihydroxybenzoyl)oxymethyl]oxolan-2-yl]methyl 3,4,5-trihydroxybenzoate
• SMILES (Canonical): C1=C(C=C(C(=C1O)O)O)C(=O)OCC2C(C(C(O2)O)(COC(=O)C3=CC(=C(C(=C3)O)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
• SMILES (Isomeric): C1=C(C=C(C(=C1O)O)O)C(=O)OCC2C(C([C@@H](O2)O)(COC(=O)C3=CC(=C(C(=C3)O)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O
• InChI: InChI=1S/C27H24O18/c28-12-1-9(2-13(29)19(12)34)23(37)42-7-18-22(45-25(39)11-5-16(32)21(36)17(33)6-11)27(41,26(40)44-18)8-43-24(38)10-3-14(30)20(35)15(31)4-10/h1-6,18,22,26,28-36,40-41H,7-8H2/t18?,22?,26-,27?/m1/s1
• InChI Key: KCQFLGUEZXYOER-IPKUFKRGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₄O₁₈
• Molecular Weight: 636.50 g/mol
• Exact Mass: 636.09626391 g/mol
• Topological Polar Surface Area (TPSA): 311.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.28
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 8

Synonyms

• UNII-MD4L7VNE2T
• D07WLU
• 1,2,6-Tri-O-galloyl-.beta.-D-glucose
• PD179130
• 1,2,6-Tri-O-galloyl-.beta.-D-glucopyranose
• .beta.-D-Glucopyranose, 1,2,6-tris(3,4,5-trihydroxybenzoate)
• [(5R)-4,5-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-4-[(3,4,5-trihydroxybenzoyl)oxymethyl]tetrahydrofuran-2-yl]methyl 3,4,5-trihydroxybenzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5619	56.19%
Caco-2	-	0.8724	87.24%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7352	73.52%
OATP2B1 inhibitior	-	0.7113	71.13%
OATP1B1 inhibitior	-	0.3379	33.79%
OATP1B3 inhibitior	+	0.9127	91.27%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.5684	56.84%
P-glycoprotein inhibitior	+	0.6907	69.07%
P-glycoprotein substrate	-	0.8542	85.42%
CYP3A4 substrate	+	0.5477	54.77%
CYP2C9 substrate	-	0.6105	61.05%
CYP2D6 substrate	-	0.8526	85.26%
CYP3A4 inhibition	-	0.8820	88.20%
CYP2C9 inhibition	-	0.8283	82.83%
CYP2C19 inhibition	-	0.8391	83.91%
CYP2D6 inhibition	-	0.9373	93.73%
CYP1A2 inhibition	-	0.8382	83.82%
CYP2C8 inhibition	-	0.5700	57.00%
CYP inhibitory promiscuity	-	0.8710	87.10%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5917	59.17%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.8299	82.99%
Skin irritation	-	0.8392	83.92%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7121	71.21%
Micronuclear	+	0.5022	50.22%
Hepatotoxicity	-	0.9125	91.25%
skin sensitisation	-	0.8277	82.77%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.8321	83.21%
Acute Oral Toxicity (c)	III	0.6618	66.18%
Estrogen receptor binding	+	0.8211	82.11%
Androgen receptor binding	+	0.6987	69.87%
Thyroid receptor binding	-	0.5117	51.17%
Glucocorticoid receptor binding	+	0.6551	65.51%
Aromatase binding	+	0.5427	54.27%
PPAR gamma	+	0.6998	69.98%
Honey bee toxicity	-	0.8542	85.42%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6650	66.50%
Fish aquatic toxicity	+	0.9626	96.26%

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	99.11%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	93.51%	95.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.09%	96.09%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	91.73%	83.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	90.96%	95.64%
CHEMBL3194	P02766	Transthyretin	89.93%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.63%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.01%	94.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	86.97%	94.42%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.31%	96.95%
CHEMBL3401	O75469	Pregnane X receptor	84.83%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.49%	99.17%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.41%	97.21%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.08%	89.34%
CHEMBL226	P30542	Adenosine A1 receptor	82.90%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.53%	89.00%
CHEMBL2581	P07339	Cathepsin D	81.98%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	80.96%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.45%	97.09%

Plants that contains it

• Cornus officinalis
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum

Cross-Links

• PubChem: 124024
• NPASS: NPC125445