(2S,3R,5R,7S,9Z,12S)-2,3,16-trihydroxy-18-methoxy-12-methyl-6,13-dioxatricyclo[13.4.0.05,7]nonadeca-1(15),9,16,18-tetraene-8,14-dione

Details

• Internal ID: 71e56750-f7e1-44c0-a09f-790f85ac91f8
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues > Zearalenones
• IUPAC Name: (2S,3R,5R,7S,9Z,12S)-2,3,16-trihydroxy-18-methoxy-12-methyl-6,13-dioxatricyclo[13.4.0.05,7]nonadeca-1(15),9,16,18-tetraene-8,14-dione
• SMILES (Canonical): CC1CC=CC(=O)C2C(O2)CC(C(C3=C(C(=CC(=C3)OC)O)C(=O)O1)O)O
• SMILES (Isomeric): C[C@H]1C/C=C\C(=O)[C@@H]2[C@H](O2)C[C@H]([C@H](C3=C(C(=CC(=C3)OC)O)C(=O)O1)O)O
• InChI: InChI=1S/C19H22O8/c1-9-4-3-5-12(20)18-15(27-18)8-14(22)17(23)11-6-10(25-2)7-13(21)16(11)19(24)26-9/h3,5-7,9,14-15,17-18,21-23H,4,8H2,1-2H3/b5-3-/t9-,14+,15+,17-,18+/m0/s1
• InChI Key: HDZUUVQEDFZKAX-BBFAGKBJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₈
• Molecular Weight: 378.40 g/mol
• Exact Mass: 378.13146766 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.03
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9533	95.33%
Caco-2	-	0.7039	70.39%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5085	50.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8774	87.74%
OATP1B3 inhibitior	+	0.9326	93.26%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7973	79.73%
P-glycoprotein inhibitior	-	0.6573	65.73%
P-glycoprotein substrate	-	0.9357	93.57%
CYP3A4 substrate	+	0.6562	65.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8579	85.79%
CYP3A4 inhibition	-	0.7207	72.07%
CYP2C9 inhibition	-	0.9227	92.27%
CYP2C19 inhibition	-	0.8828	88.28%
CYP2D6 inhibition	-	0.8981	89.81%
CYP1A2 inhibition	-	0.8429	84.29%
CYP2C8 inhibition	-	0.6287	62.87%
CYP inhibitory promiscuity	-	0.9812	98.12%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.5053	50.53%
Eye corrosion	-	0.9761	97.61%
Eye irritation	-	0.9502	95.02%
Skin irritation	-	0.7027	70.27%
Skin corrosion	-	0.9264	92.64%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6397	63.97%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.7236	72.36%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5572	55.72%
Acute Oral Toxicity (c)	III	0.4539	45.39%
Estrogen receptor binding	+	0.7099	70.99%
Androgen receptor binding	+	0.6991	69.91%
Thyroid receptor binding	-	0.6236	62.36%
Glucocorticoid receptor binding	+	0.8141	81.41%
Aromatase binding	+	0.5394	53.94%
PPAR gamma	+	0.5755	57.55%
Honey bee toxicity	-	0.8235	82.35%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9321	93.21%

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	99.30%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.07%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.59%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	94.22%	91.07%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.69%	97.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.66%	93.99%
CHEMBL4208	P20618	Proteasome component C5	92.48%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.33%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.01%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.87%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.97%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.12%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.09%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.08%	86.33%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	85.96%	82.67%
CHEMBL3401	O75469	Pregnane X receptor	85.95%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.49%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.32%	92.62%
CHEMBL2581	P07339	Cathepsin D	84.22%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.84%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	83.72%	91.19%
CHEMBL2535	P11166	Glucose transporter	83.62%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.62%	97.14%
CHEMBL4530	P00488	Coagulation factor XIII	83.21%	96.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.17%	96.77%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.41%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	82.18%	94.75%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.71%	96.95%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	80.50%	80.00%

Plants that contains it

• Hypericum geminiflorum

Cross-Links

• PubChem: 163185336
• LOTUS: LTS0086420
• wikiData: Q105145563