[2-(Hydroxymethyl)-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: 671c661e-21b6-477b-aca9-248a061230b0
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [2-(hydroxymethyl)-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=COC(C2C1C(C3C2(O3)CO)OC(=O)C=CC4=CC(=C(C=C4)O)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): C1=COC(C2C1C(C3C2(O3)CO)OC(=O)C=CC4=CC(=C(C=C4)O)O)OC5C(C(C(C(O5)CO)O)O)O
• InChI: InChI=1S/C24H28O13/c25-8-14-17(30)18(31)19(32)23(34-14)36-22-16-11(5-6-33-22)20(21-24(16,9-26)37-21)35-15(29)4-2-10-1-3-12(27)13(28)7-10/h1-7,11,14,16-23,25-28,30-32H,8-9H2
• InChI Key: MZQXNUBTVLKMLP-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₁₃
• Molecular Weight: 524.50 g/mol
• Exact Mass: 524.15299094 g/mol
• Topological Polar Surface Area (TPSA): 208.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -1.91
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6226	62.26%
Caco-2	-	0.9265	92.65%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5735	57.35%
OATP2B1 inhibitior	-	0.8513	85.13%
OATP1B1 inhibitior	+	0.8480	84.80%
OATP1B3 inhibitior	+	0.9546	95.46%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6071	60.71%
P-glycoprotein inhibitior	-	0.6626	66.26%
P-glycoprotein substrate	-	0.6869	68.69%
CYP3A4 substrate	+	0.6627	66.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8658	86.58%
CYP3A4 inhibition	-	0.9007	90.07%
CYP2C9 inhibition	-	0.8754	87.54%
CYP2C19 inhibition	-	0.7104	71.04%
CYP2D6 inhibition	-	0.8588	85.88%
CYP1A2 inhibition	-	0.8529	85.29%
CYP2C8 inhibition	+	0.6456	64.56%
CYP inhibitory promiscuity	-	0.7400	74.00%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5794	57.94%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9366	93.66%
Skin irritation	-	0.7722	77.22%
Skin corrosion	-	0.9454	94.54%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6509	65.09%
Micronuclear	+	0.5233	52.33%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.7644	76.44%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8269	82.69%
Acute Oral Toxicity (c)	III	0.4480	44.80%
Estrogen receptor binding	+	0.7255	72.55%
Androgen receptor binding	+	0.5434	54.34%
Thyroid receptor binding	+	0.5937	59.37%
Glucocorticoid receptor binding	-	0.5193	51.93%
Aromatase binding	+	0.6129	61.29%
PPAR gamma	+	0.7650	76.50%
Honey bee toxicity	-	0.7115	71.15%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8031	80.31%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	348 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.87%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.77%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.45%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.33%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.93%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.36%	96.00%
CHEMBL3194	P02766	Transthyretin	91.22%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.22%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.36%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	86.88%	94.73%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.08%	80.78%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.98%	94.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.57%	94.62%
CHEMBL4208	P20618	Proteasome component C5	85.44%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.11%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.33%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.31%	86.92%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.36%	94.08%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.45%	99.15%

Plants that contains it

• Kigelia africana
• Stereospermum acuminatissimum
• Stereospermum cylindricum
• Veronica alpina
• Veronica anagallis-aquatica
• Veronica hederifolia
• Veronica longifolia
• Veronica orientalis
• Veronica persica
• Veronica thomsonii

Cross-Links

• PubChem: 73150574
• LOTUS: LTS0239284
• wikiData: Q105175979