5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

Details

• Internal ID: aa817837-8a3b-43a8-8080-d090febc7fde
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)C4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
• InChI: InChI=1S/C21H20O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14-,17-,19+,20-,21-/m1/s1
• InChI Key: MYXNWGACZJSMBT-IAAKTDFRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₀
• Molecular Weight: 432.40 g/mol
• Exact Mass: 432.10564683 g/mol
• Topological Polar Surface Area (TPSA): 177.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.09
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6665	66.65%
Caco-2	-	0.9294	92.94%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5728	57.28%
OATP2B1 inhibitior	+	0.5914	59.14%
OATP1B1 inhibitior	+	0.8337	83.37%
OATP1B3 inhibitior	+	0.9709	97.09%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.7033	70.33%
P-glycoprotein inhibitior	-	0.7213	72.13%
P-glycoprotein substrate	-	0.8425	84.25%
CYP3A4 substrate	+	0.5737	57.37%
CYP2C9 substrate	-	0.6194	61.94%
CYP2D6 substrate	-	0.8416	84.16%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9240	92.40%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	-	0.8355	83.55%
CYP2C8 inhibition	+	0.7200	72.00%
CYP inhibitory promiscuity	-	0.7806	78.06%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7252	72.52%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.8162	81.62%
Skin irritation	-	0.7691	76.91%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	+	0.5129	51.29%
Human Ether-a-go-go-Related Gene inhibition	-	0.5965	59.65%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	-	0.7571	75.71%
skin sensitisation	-	0.8683	86.83%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8611	86.11%
Acute Oral Toxicity (c)	IV	0.3746	37.46%
Estrogen receptor binding	+	0.6482	64.82%
Androgen receptor binding	+	0.7702	77.02%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6709	67.09%
Aromatase binding	+	0.6039	60.39%
PPAR gamma	+	0.7702	77.02%
Honey bee toxicity	-	0.7541	75.41%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.6921	69.21%

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	99.48%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.60%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.80%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.54%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.31%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.41%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.88%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.35%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.92%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.78%	85.14%
CHEMBL3194	P02766	Transthyretin	84.68%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.26%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.42%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.27%	86.92%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.10%	91.71%
CHEMBL3038469	P24941	CDK2/Cyclin A	82.70%	91.38%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	82.34%	89.23%
CHEMBL220	P22303	Acetylcholinesterase	82.13%	94.45%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.05%	94.45%

Plants that contains it

• Acacia pycnantha
• Afrocarpus falcatus
• Aloe vera
• Asterogyne martiana
• Baccharis magellanica
• Beilschmiedia volckii
• Berkheya zeyheri
• Beta vulgaris
• Canella winterana
• Carlina acaulis
• Chrysosplenium echinus
• Cirsium nipponicum var. incomptum
• Clausena lansium
• Daphne giraldii
• Daphne sericea
• Desmodium canadense
• Eumorphia sericea
• Eupatorium cannabinum subsp. cannabinum
• Flemingia chappar
• Garcinia pseudoguttifera
• Glycyrrhiza glabra
• Gutierrezia microcephala
• Justicia buchii
• Ligularia lamarum
• Lippia mexicana
• Narcissus obesus
• Nicotiana forsteri
• Ocotea pulchella
• Parkinsonia aculeata
• Passiflora bryonioides
• Passiflora platyloba
• Philotheca thryptomenoides
• Salvia digitaloides
• Salvia fruticosa
• Seriphidium herba-alba
• Sophora exigua
• Sporobolus cynosuroides
• Thalictrum cultratum
• Thermopsis alpina
• Thlaspi arvense
• Turricula parryi
• Uncaria laevigata
• Vepris heterophylla
• Xanthium pungens

Cross-Links

• PubChem: 57511421
• NPASS: NPC189958
• LOTUS: LTS0174203
• wikiData: Q105175273