(2R,3R)-3-hydroxy-7-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydrochromen-4-one

Details

• Internal ID: 4698ce11-3f4d-4611-aa5d-0c68219b0c09
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: (2R,3R)-3-hydroxy-7-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=CC2=C(C(=C1)OC3C(C(C(C(O3)CO)O)O)O)C(=O)C(C(O2)C4=CC=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): COC1=CC2=C(C(=C1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)[C@@H]([C@H](O2)C4=CC=C(C=C4)O[C@@H]5[C@H]([C@@H]([C@H]([C@@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C28H34O16/c1-39-12-6-13-17(14(7-12)42-28-25(38)22(35)19(32)16(9-30)44-28)20(33)23(36)26(41-13)10-2-4-11(5-3-10)40-27-24(37)21(34)18(31)15(8-29)43-27/h2-7,15-16,18-19,21-32,34-38H,8-9H2,1H3/t15-,16+,18-,19+,21+,22-,23-,24-,25+,26+,27-,28+/m0/s1
• InChI Key: UFVGIXNFCCIZHZ-VTDMTTMCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₄O₁₆
• Molecular Weight: 626.60 g/mol
• Exact Mass: 626.18468499 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -3.27
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5457	54.57%
Caco-2	-	0.8930	89.30%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5961	59.61%
OATP2B1 inhibitior	-	0.8498	84.98%
OATP1B1 inhibitior	+	0.9088	90.88%
OATP1B3 inhibitior	+	0.9786	97.86%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7048	70.48%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.8703	87.03%
CYP3A4 substrate	+	0.5961	59.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8275	82.75%
CYP3A4 inhibition	-	0.9437	94.37%
CYP2C9 inhibition	-	0.9060	90.60%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.9150	91.50%
CYP2C8 inhibition	-	0.6411	64.11%
CYP inhibitory promiscuity	-	0.7142	71.42%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6642	66.42%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9104	91.04%
Skin irritation	-	0.8320	83.20%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7152	71.52%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.6466	64.66%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.5121	51.21%
Acute Oral Toxicity (c)	III	0.6678	66.78%
Estrogen receptor binding	+	0.8095	80.95%
Androgen receptor binding	+	0.5461	54.61%
Thyroid receptor binding	-	0.5122	51.22%
Glucocorticoid receptor binding	-	0.5692	56.92%
Aromatase binding	-	0.4920	49.20%
PPAR gamma	+	0.7179	71.79%
Honey bee toxicity	-	0.8204	82.04%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.6698	66.98%

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	98.24%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.76%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.96%	85.14%
CHEMBL2581	P07339	Cathepsin D	92.62%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.11%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.99%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	91.89%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.45%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.15%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.25%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.57%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.52%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.43%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.04%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.32%	92.62%

Plants that contains it

• Ageratina ligustrina
• Salvia regla

Cross-Links

• PubChem: 163033744
• LOTUS: LTS0149296
• wikiData: Q105305447