5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]-2,3-dihydrochromen-4-one

Details

• Internal ID: 5d131039-be6b-418e-937f-0cea60dbf19e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=C(C(=CC(=C2C1=O)O)O)C3C(C(C(C(O3)COC4C(C(C(C(O4)CO)O)O)O)O)O)O)C5=CC=C(C=C5)O
• SMILES (Isomeric): C1C(OC2=C(C(=CC(=C2C1=O)O)O)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O)C5=CC=C(C=C5)O
• InChI: InChI=1S/C27H32O15/c28-7-15-19(33)22(36)24(38)27(42-15)39-8-16-20(34)21(35)23(37)26(41-16)18-12(31)5-11(30)17-13(32)6-14(40-25(17)18)9-1-3-10(29)4-2-9/h1-5,14-16,19-24,26-31,33-38H,6-8H2/t14?,15-,16-,19-,20-,21+,22+,23-,24-,26+,27-/m1/s1
• InChI Key: KGMWNTRZODYLCW-BJZLFXGNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₁₅
• Molecular Weight: 596.50 g/mol
• Exact Mass: 596.17412031 g/mol
• Topological Polar Surface Area (TPSA): 256.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.15
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9271	92.71%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.8477	84.77%
OATP1B1 inhibitior	+	0.8659	86.59%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5529	55.29%
P-glycoprotein inhibitior	-	0.6996	69.96%
P-glycoprotein substrate	-	0.7995	79.95%
CYP3A4 substrate	+	0.6241	62.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8406	84.06%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9315	93.15%
CYP2C19 inhibition	-	0.9047	90.47%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9180	91.80%
CYP2C8 inhibition	+	0.5802	58.02%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8965	89.65%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.5471	54.71%
Human Ether-a-go-go-Related Gene inhibition	+	0.7253	72.53%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5516	55.16%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.7655	76.55%
Androgen receptor binding	+	0.5961	59.61%
Thyroid receptor binding	-	0.4924	49.24%
Glucocorticoid receptor binding	-	0.5633	56.33%
Aromatase binding	+	0.5619	56.19%
PPAR gamma	+	0.7015	70.15%
Honey bee toxicity	-	0.7536	75.36%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.7958	79.58%

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	99.52%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.19%	97.09%
CHEMBL2581	P07339	Cathepsin D	95.15%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.13%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.48%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.49%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	88.55%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.34%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.17%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.45%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.26%	99.15%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.80%	96.21%
CHEMBL226	P30542	Adenosine A1 receptor	84.55%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.05%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.41%	99.17%
CHEMBL4208	P20618	Proteasome component C5	82.85%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.42%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.23%	99.23%

Plants that contains it

• Piper umbellatum

Cross-Links

• PubChem: 163075995
• LOTUS: LTS0150113
• wikiData: Q105140852