[(2R,3S,4S,5R,6S)-6-[2-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-6-oxopyran-4-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: fe10c340-01eb-40a3-87aa-d14ab0d1c67d
• Taxonomy: Phenylpropanoids and polyketides > Kavalactones
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[2-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-6-oxopyran-4-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=C(C=C1C=CC2=CC(=CC(=O)O2)OC3C(C(C(C(O3)COC(=O)C=CC4=CC(=C(C=C4)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C/C2=CC(=CC(=O)O2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O)O)O)O
• InChI: InChI=1S/C28H26O13/c29-18-6-2-14(9-20(18)31)1-5-16-11-17(12-24(34)39-16)40-28-27(37)26(36)25(35)22(41-28)13-38-23(33)8-4-15-3-7-19(30)21(32)10-15/h1-12,22,25-32,35-37H,13H2/b5-1+,8-4+/t22-,25-,26+,27-,28-/m1/s1
• InChI Key: GKIGHGLGNQIWAP-MLRIOAKVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₆O₁₃
• Molecular Weight: 570.50 g/mol
• Exact Mass: 570.13734088 g/mol
• Topological Polar Surface Area (TPSA): 213.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.08
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7597	75.97%
Caco-2	-	0.8987	89.87%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5954	59.54%
OATP2B1 inhibitior	-	0.6982	69.82%
OATP1B1 inhibitior	+	0.9242	92.42%
OATP1B3 inhibitior	+	0.9268	92.68%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.7918	79.18%
P-glycoprotein inhibitior	+	0.6132	61.32%
P-glycoprotein substrate	-	0.8589	85.89%
CYP3A4 substrate	+	0.5905	59.05%
CYP2C9 substrate	-	0.8091	80.91%
CYP2D6 substrate	-	0.8735	87.35%
CYP3A4 inhibition	-	0.8258	82.58%
CYP2C9 inhibition	-	0.8218	82.18%
CYP2C19 inhibition	-	0.8801	88.01%
CYP2D6 inhibition	-	0.9242	92.42%
CYP1A2 inhibition	-	0.9406	94.06%
CYP2C8 inhibition	+	0.6250	62.50%
CYP inhibitory promiscuity	-	0.8191	81.91%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7077	70.77%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.8836	88.36%
Skin irritation	-	0.8342	83.42%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4074	40.74%
Micronuclear	+	0.6166	61.66%
Hepatotoxicity	-	0.8196	81.96%
skin sensitisation	-	0.8086	80.86%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.8849	88.49%
Acute Oral Toxicity (c)	III	0.6844	68.44%
Estrogen receptor binding	+	0.7517	75.17%
Androgen receptor binding	+	0.7456	74.56%
Thyroid receptor binding	+	0.5531	55.31%
Glucocorticoid receptor binding	+	0.5786	57.86%
Aromatase binding	-	0.5103	51.03%
PPAR gamma	+	0.7033	70.33%
Honey bee toxicity	-	0.7886	78.86%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9539	95.39%

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	99.80%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.87%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.89%	86.33%
CHEMBL3194	P02766	Transthyretin	94.75%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.68%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.08%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.95%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.12%	99.15%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	87.83%	80.78%
CHEMBL3401	O75469	Pregnane X receptor	86.59%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.10%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.69%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.09%	97.09%
CHEMBL4208	P20618	Proteasome component C5	84.03%	90.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	83.61%	85.31%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.57%	83.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.15%	94.00%
CHEMBL2581	P07339	Cathepsin D	81.59%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.35%	96.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.18%	90.71%

Plants that contains it

• Clematis tashiroi

Cross-Links

• PubChem: 122181709
• LOTUS: LTS0263359
• wikiData: Q105010033