(2R,3S)-2-phenyl-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-chromene-3,5,7-triol

Details

• Internal ID: 7d41ca7d-a765-4e3e-9471-21c03ab9f976
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: (2R,3S)-2-phenyl-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• SMILES (Canonical): C1C(C(OC2=C1C(=C(C(=C2)O)C3C(C(C(C(O3)CO)O)O)O)O)C4=CC=CC=C4)O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=C1C(=C(C(=C2)O)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)C4=CC=CC=C4)O
• InChI: InChI=1S/C21H24O9/c22-8-14-17(26)18(27)19(28)21(30-14)15-11(23)7-13-10(16(15)25)6-12(24)20(29-13)9-4-2-1-3-5-9/h1-5,7,12,14,17-28H,6,8H2/t12-,14+,17+,18-,19+,20+,21-/m0/s1
• InChI Key: BIYKQORLKNDMIR-CPKJHJHWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₉
• Molecular Weight: 420.40 g/mol
• Exact Mass: 420.14203234 g/mol
• Topological Polar Surface Area (TPSA): 160.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.35
• H-Bond Acceptor: 9
• 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	+	0.6354	63.54%
Caco-2	-	0.9204	92.04%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Nucleus	0.4480	44.80%
OATP2B1 inhibitior	-	0.5704	57.04%
OATP1B1 inhibitior	+	0.7524	75.24%
OATP1B3 inhibitior	+	0.9713	97.13%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8004	80.04%
P-glycoprotein inhibitior	-	0.7592	75.92%
P-glycoprotein substrate	-	0.8619	86.19%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3872	38.72%
CYP3A4 inhibition	-	0.9014	90.14%
CYP2C9 inhibition	-	0.9446	94.46%
CYP2C19 inhibition	-	0.9185	91.85%
CYP2D6 inhibition	-	0.9166	91.66%
CYP1A2 inhibition	-	0.9124	91.24%
CYP2C8 inhibition	+	0.5104	51.04%
CYP inhibitory promiscuity	-	0.8647	86.47%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6685	66.85%
Eye corrosion	-	0.9943	99.43%
Eye irritation	-	0.9105	91.05%
Skin irritation	-	0.7763	77.63%
Skin corrosion	-	0.9580	95.80%
Ames mutagenesis	-	0.5606	56.06%
Human Ether-a-go-go-Related Gene inhibition	-	0.4158	41.58%
Micronuclear	+	0.6159	61.59%
Hepatotoxicity	-	0.7552	75.52%
skin sensitisation	-	0.8594	85.94%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8306	83.06%
Acute Oral Toxicity (c)	III	0.4032	40.32%
Estrogen receptor binding	+	0.6716	67.16%
Androgen receptor binding	+	0.5591	55.91%
Thyroid receptor binding	+	0.6673	66.73%
Glucocorticoid receptor binding	-	0.4898	48.98%
Aromatase binding	+	0.7220	72.20%
PPAR gamma	+	0.8550	85.50%
Honey bee toxicity	-	0.8682	86.82%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	-	0.4731	47.31%

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	99.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.17%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	93.34%	83.82%
CHEMBL2581	P07339	Cathepsin D	91.00%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	89.53%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.10%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.08%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.50%	94.73%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	85.79%	96.37%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.39%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.89%	89.00%

Plants that contains it

• Dryopteris crassirhizoma

Cross-Links

• PubChem: 163103522
• LOTUS: LTS0143992
• wikiData: Q104936884