[(2S,3R,4R,5R,6S)-2-[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy-4,5-dihydroxy-6-methyloxan-3-yl] 3,4,5-trihydroxybenzoate

Details

• Internal ID: aabfd5a9-4c8f-45d5-98f5-94963c559819
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2S,3R,4R,5R,6S)-2-[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy-4,5-dihydroxy-6-methyloxan-3-yl] 3,4,5-trihydroxybenzoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)O)O
• InChI: InChI=1S/C28H24O16/c1-8-19(35)23(39)26(43-27(40)10-4-15(33)21(37)16(34)5-10)28(41-8)44-25-22(38)18-12(30)6-11(29)7-17(18)42-24(25)9-2-13(31)20(36)14(32)3-9/h2-8,19,23,26,28-37,39H,1H3/t8-,19-,23+,26+,28-/m0/s1
• InChI Key: IXDHJNNHLVGCLC-MXXRNXGISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₄O₁₆
• Molecular Weight: 616.50 g/mol
• Exact Mass: 616.10643467 g/mol
• Topological Polar Surface Area (TPSA): 273.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.18
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 5

Synonyms

• 56939-52-7
• 2''-O-Galloylmyricitrin
• [(2S,3R,4R,5R,6S)-2-[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy-4,5-dihydroxy-6-methyloxan-3-yl] 3,4,5-trihydroxybenzoate
• Desmanthin-1
• 2'-O-Galloylmyricitrin
• SCHEMBL2963374
• CHEMBL2152656
• AKOS040761013
• Myricetin3-O-(2''-O-galloyl)-rhamnoside
• NCGC00385142-01![(2S,3R,4R,5R,6S)-2-[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy-4,5-dihydroxy-6-methyloxan-3-yl] 3,4,5-trihydroxybenzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7495	74.95%
Caco-2	-	0.8722	87.22%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7171	71.71%
OATP2B1 inhibitior	-	0.5540	55.40%
OATP1B1 inhibitior	+	0.7145	71.45%
OATP1B3 inhibitior	+	0.9745	97.45%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6652	66.52%
P-glycoprotein inhibitior	+	0.7034	70.34%
P-glycoprotein substrate	+	0.5446	54.46%
CYP3A4 substrate	+	0.6557	65.57%
CYP2C9 substrate	-	0.6564	65.64%
CYP2D6 substrate	-	0.8709	87.09%
CYP3A4 inhibition	-	0.8307	83.07%
CYP2C9 inhibition	-	0.8102	81.02%
CYP2C19 inhibition	-	0.8717	87.17%
CYP2D6 inhibition	-	0.9680	96.80%
CYP1A2 inhibition	-	0.6999	69.99%
CYP2C8 inhibition	+	0.8500	85.00%
CYP inhibitory promiscuity	-	0.7743	77.43%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6314	63.14%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.8701	87.01%
Skin irritation	-	0.6672	66.72%
Skin corrosion	-	0.9176	91.76%
Ames mutagenesis	+	0.5763	57.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.7464	74.64%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.5447	54.47%
skin sensitisation	-	0.9127	91.27%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.9367	93.67%
Acute Oral Toxicity (c)	III	0.5185	51.85%
Estrogen receptor binding	+	0.7904	79.04%
Androgen receptor binding	+	0.7241	72.41%
Thyroid receptor binding	+	0.5506	55.06%
Glucocorticoid receptor binding	+	0.7021	70.21%
Aromatase binding	-	0.5311	53.11%
PPAR gamma	+	0.7286	72.86%
Honey bee toxicity	-	0.8252	82.52%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5250	52.50%
Fish aquatic toxicity	+	0.9611	96.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.51%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.31%	91.11%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	99.09%	95.64%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.42%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.77%	98.95%
CHEMBL3194	P02766	Transthyretin	95.43%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.78%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.26%	94.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	92.71%	94.42%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.26%	99.17%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	90.38%	83.00%
CHEMBL3401	O75469	Pregnane X receptor	90.25%	94.73%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	90.23%	81.11%
CHEMBL4208	P20618	Proteasome component C5	87.72%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.41%	99.23%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	86.15%	97.53%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.11%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.39%	95.78%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.74%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.31%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.86%	97.36%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.51%	80.78%
CHEMBL4530	P00488	Coagulation factor XIII	80.62%	96.00%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	80.29%	87.67%

Plants that contains it

• Ajuga genevensis
• Angelica lucida
• Boronia pinnata
• Brocchia cinerea
• Castanea sativa
• Cleistanthus indochinensis
• Cleome spinosa
• Cyrtomium falcatum
• Daphniphyllum paxianum
• Desmanthus illinoensis
• Diospyros japonica
• Elymus repens
• Eugenia myrcianthes
• Glochidion sphaerogynum
• Hymenoxys insignis
• Inga laurina
• Lespedeza bicolor
• Limonium sinense
• Melaleuca quinquenervia
• Mimusops caffra
• Myrcia multiflora
• Myrica rubra
• Neonauclea sessilifolia
• Nerine bowdenii
• Phedimus selskianus
• Pinguicula vulgaris
• Polygonum aviculare
• Pongamiopsis pervilleana
• Semialarium mexicanum
• Sesbania bispinosa
• Solidago serotina
• Sorbaria sorbifolia
• Strophanthus kombe
• Syzygium samarangense
• Veronica arvensis

Cross-Links

• PubChem: 5316590
• NPASS: NPC217387
• LOTUS: LTS0243833
• wikiData: Q104667336