[(1S,2R,4S,5S,6S,10S)-6-hydroxy-2-methyl-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] (Z)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 8f8c79f5-9253-40e5-ba6b-0bc99baa7205
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(1S,2R,4S,5S,6S,10S)-6-hydroxy-2-methyl-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] (Z)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC12C3C(OC=CC3(C(C1O2)OC(=O)C=CC4=CC=C(C=C4)O)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): C[C@@]12[C@H]3[C@@H](OC=C[C@]3([C@H]([C@@H]1O2)OC(=O)/C=C\C4=CC=C(C=C4)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C24H28O12/c1-23-18-22(35-21-17(30)16(29)15(28)13(10-25)33-21)32-9-8-24(18,31)20(19(23)36-23)34-14(27)7-4-11-2-5-12(26)6-3-11/h2-9,13,15-22,25-26,28-31H,10H2,1H3/b7-4-/t13-,15-,16+,17-,18-,19+,20+,21+,22+,23-,24+/m1/s1
• InChI Key: FUUBBPBQJSJZFW-UZMALFMMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₁₂
• Molecular Weight: 508.50 g/mol
• Exact Mass: 508.15807632 g/mol
• Topological Polar Surface Area (TPSA): 188.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.48
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6801	68.01%
Caco-2	-	0.8927	89.27%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6619	66.19%
OATP2B1 inhibitior	-	0.8525	85.25%
OATP1B1 inhibitior	+	0.8284	82.84%
OATP1B3 inhibitior	+	0.9595	95.95%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6133	61.33%
P-glycoprotein inhibitior	-	0.6423	64.23%
P-glycoprotein substrate	-	0.6221	62.21%
CYP3A4 substrate	+	0.6764	67.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8771	87.71%
CYP3A4 inhibition	-	0.9009	90.09%
CYP2C9 inhibition	-	0.8963	89.63%
CYP2C19 inhibition	-	0.8340	83.40%
CYP2D6 inhibition	-	0.9094	90.94%
CYP1A2 inhibition	-	0.8618	86.18%
CYP2C8 inhibition	+	0.7097	70.97%
CYP inhibitory promiscuity	-	0.7164	71.64%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5482	54.82%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9476	94.76%
Skin irritation	-	0.7545	75.45%
Skin corrosion	-	0.9419	94.19%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6507	65.07%
Micronuclear	+	0.5033	50.33%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.7958	79.58%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.4799	47.99%
Acute Oral Toxicity (c)	III	0.4951	49.51%
Estrogen receptor binding	+	0.7693	76.93%
Androgen receptor binding	+	0.6757	67.57%
Thyroid receptor binding	+	0.6376	63.76%
Glucocorticoid receptor binding	+	0.6595	65.95%
Aromatase binding	+	0.6235	62.35%
PPAR gamma	+	0.6916	69.16%
Honey bee toxicity	-	0.7472	74.72%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6855	68.55%
Fish aquatic toxicity	+	0.7890	78.90%

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	99.22%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.63%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.27%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.87%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.30%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	90.18%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.93%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.91%	89.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.27%	97.28%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	85.05%	93.10%
CHEMBL226	P30542	Adenosine A1 receptor	84.58%	95.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.01%	99.17%
CHEMBL4040	P28482	MAP kinase ERK2	83.96%	83.82%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.90%	89.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.01%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.94%	95.50%
CHEMBL3194	P02766	Transthyretin	81.34%	90.71%
CHEMBL2581	P07339	Cathepsin D	81.24%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.90%	95.89%
CHEMBL206	P03372	Estrogen receptor alpha	80.07%	97.64%

Plants that contains it

• Linaria vulgaris

Cross-Links

• PubChem: 163193124
• LOTUS: LTS0063228
• wikiData: Q105002014