(3,4-Dihydroxyphenyl)[2,4,6-trihydroxy-3-[2-O-(4-hydroxybenzoyl)-6-O-(3,4,5-trihydroxybenzoyl)-beta-D-glucopyranosyl]phenyl]methanone

Details

• Internal ID: ae4faa49-50af-4820-8c86-bb5e7c39bd03
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[3-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxyphenyl]-3,4-dihydroxy-5-(4-hydroxybenzoyl)oxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• SMILES (Canonical): C1=CC(=CC=C1C(=O)OC2C(C(C(OC2C3=C(C(=C(C=C3O)O)C(=O)C4=CC(=C(C=C4)O)O)O)COC(=O)C5=CC(=C(C(=C5)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C(=O)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2C3=C(C(=C(C=C3O)O)C(=O)C4=CC(=C(C=C4)O)O)O)COC(=O)C5=CC(=C(C(=C5)O)O)O)O)O)O
• InChI: InChI=1S/C33H28O17/c34-15-4-1-12(2-5-15)33(47)50-31-29(45)27(43)22(11-48-32(46)14-8-20(39)26(42)21(40)9-14)49-30(31)24-19(38)10-18(37)23(28(24)44)25(41)13-3-6-16(35)17(36)7-13/h1-10,22,27,29-31,34-40,42-45H,11H2/t22-,27-,29+,30+,31-/m1/s1
• InChI Key: KLKOBSQIPPYKDT-JMPMIDNKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₂₈O₁₇
• Molecular Weight: 696.60 g/mol
• Exact Mass: 696.13264942 g/mol
• Topological Polar Surface Area (TPSA): 301.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.51
• H-Bond Acceptor: 17
• H-Bond Donor: 11
• Rotatable Bonds: 8

Synonyms

• (3,4-Dihydroxyphenyl)[2,4,6-trihydroxy-3-[2-O-(4-hydroxybenzoyl)-6-O-(3,4,5-trihydroxybenzoyl)-beta-D-glucopyranosyl]phenyl]methanone
• 3-[6-O-(3,4,5-Trihydroxybenzoyl)-2-O-(4-hydroxybenzoyl)-beta-D-glucopyranosyl]-2,3',4,4',6-pentahydroxybenzophenone
• 92631-85-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7314	73.14%
Caco-2	-	0.9077	90.77%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7181	71.81%
OATP2B1 inhibitior	-	0.5629	56.29%
OATP1B1 inhibitior	-	0.3414	34.14%
OATP1B3 inhibitior	+	0.8056	80.56%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.7735	77.35%
P-glycoprotein inhibitior	+	0.7042	70.42%
P-glycoprotein substrate	-	0.7252	72.52%
CYP3A4 substrate	+	0.6186	61.86%
CYP2C9 substrate	-	0.8109	81.09%
CYP2D6 substrate	-	0.8532	85.32%
CYP3A4 inhibition	-	0.9032	90.32%
CYP2C9 inhibition	-	0.8016	80.16%
CYP2C19 inhibition	-	0.9140	91.40%
CYP2D6 inhibition	-	0.9511	95.11%
CYP1A2 inhibition	-	0.9338	93.38%
CYP2C8 inhibition	+	0.8419	84.19%
CYP inhibitory promiscuity	-	0.7871	78.71%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7276	72.76%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.8649	86.49%
Skin irritation	-	0.8471	84.71%
Skin corrosion	-	0.9605	96.05%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7508	75.08%
Micronuclear	+	0.6966	69.66%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.9049	90.49%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.9378	93.78%
Acute Oral Toxicity (c)	III	0.6755	67.55%
Estrogen receptor binding	+	0.6980	69.80%
Androgen receptor binding	+	0.7626	76.26%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.6044	60.44%
PPAR gamma	+	0.6434	64.34%
Honey bee toxicity	-	0.8466	84.66%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9318	93.18%

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	99.21%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.06%	91.49%
CHEMBL226	P30542	Adenosine A1 receptor	95.82%	95.93%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	95.22%	83.00%
CHEMBL3194	P02766	Transthyretin	95.07%	90.71%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	94.40%	95.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.17%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.98%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.83%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	90.49%	94.73%
CHEMBL4208	P20618	Proteasome component C5	88.23%	90.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	86.79%	95.64%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.50%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.89%	97.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.36%	97.21%
CHEMBL3891	P07384	Calpain 1	83.26%	93.04%
CHEMBL2581	P07339	Cathepsin D	82.76%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.58%	94.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.76%	94.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.41%	96.95%

Plants that contains it

• Aconitum burnatii
• Alseodaphne paludosa
• Annona impressivenia
• Bersama yangambiensis
• Caloncoba echinata
• Castanopsis sclerophylla
• Conocephalum japonicum
• Cordylanthus kingii
• Croton cascarilloides
• Disynaphia halimifolia
• Eragrostis viscosa
• Forsteronia refracta
• Fridericia chica
• Grewia mollis
• Gymnocarpium robertianum
• Heliotropium floridum
• Heterotheca grandiflora
• Hovenia acerba
• Juglans nigra
• Kaempferia marginata
• Kaunia saltensis
• Mangifera indica
• Nauclea officinalis
• Ruta pinnata
• Salvia dorrii
• Sophora flavescens var. flavescens
• Stevia polycephala
• Teucrium cubense
• Thymus piperella
• Trichilia rubescens
• Uraria picta

Cross-Links

• PubChem: 102076688
• NPASS: NPC6941