[(1R,2R,4R,6R,8S,9Z,11R)-8-hydroxy-9-(hydroxymethyl)-4-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.04,6]tetradec-9-en-2-yl] (2R)-2-methylbutanoate

Details

• Internal ID: d8ee1129-7434-4902-86e4-3fa276f561f6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(1R,2R,4R,6R,8S,9Z,11R)-8-hydroxy-9-(hydroxymethyl)-4-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.04,6]tetradec-9-en-2-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CC2(C(O2)CC(C(=CC3C1C(=C)C(=O)O3)CO)O)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@@H]1C[C@@]2([C@H](O2)C[C@@H](/C(=C\[C@@H]3[C@@H]1C(=C)C(=O)O3)/CO)O)C
• InChI: InChI=1S/C20H28O7/c1-5-10(2)18(23)26-15-8-20(4)16(27-20)7-13(22)12(9-21)6-14-17(15)11(3)19(24)25-14/h6,10,13-17,21-22H,3,5,7-9H2,1-2,4H3/b12-6-/t10-,13+,14-,15-,16-,17+,20-/m1/s1
• InChI Key: TZBBUVFNZDBEEJ-ZOCZKFMISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₇
• Molecular Weight: 380.40 g/mol
• Exact Mass: 380.18350323 g/mol
• Topological Polar Surface Area (TPSA): 106.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.27
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9651	96.51%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5623	56.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8790	87.90%
OATP1B3 inhibitior	+	0.9514	95.14%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.8614	86.14%
BSEP inhibitior	-	0.6171	61.71%
P-glycoprotein inhibitior	-	0.6240	62.40%
P-glycoprotein substrate	-	0.5571	55.71%
CYP3A4 substrate	+	0.6543	65.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8818	88.18%
CYP3A4 inhibition	+	0.6634	66.34%
CYP2C9 inhibition	-	0.7221	72.21%
CYP2C19 inhibition	-	0.8437	84.37%
CYP2D6 inhibition	-	0.9348	93.48%
CYP1A2 inhibition	-	0.7880	78.80%
CYP2C8 inhibition	-	0.6422	64.22%
CYP inhibitory promiscuity	-	0.8635	86.35%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5750	57.50%
Eye corrosion	-	0.9849	98.49%
Eye irritation	-	0.9225	92.25%
Skin irritation	-	0.5917	59.17%
Skin corrosion	-	0.9327	93.27%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4680	46.80%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.8580	85.80%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.6271	62.71%
Acute Oral Toxicity (c)	III	0.4525	45.25%
Estrogen receptor binding	+	0.8006	80.06%
Androgen receptor binding	+	0.6550	65.50%
Thyroid receptor binding	-	0.4879	48.79%
Glucocorticoid receptor binding	+	0.8291	82.91%
Aromatase binding	+	0.5314	53.14%
PPAR gamma	-	0.5831	58.31%
Honey bee toxicity	-	0.6932	69.32%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9869	98.69%

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	96.19%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.08%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	96.04%	97.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.66%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	93.97%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.64%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.13%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.31%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.85%	86.33%
CHEMBL2581	P07339	Cathepsin D	86.90%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.70%	95.56%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	86.01%	94.23%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.29%	96.47%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.94%	89.00%
CHEMBL299	P17252	Protein kinase C alpha	83.81%	98.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.06%	97.14%
CHEMBL230	P35354	Cyclooxygenase-2	81.91%	89.63%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.73%	95.50%
CHEMBL226	P30542	Adenosine A1 receptor	80.96%	95.93%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.94%	93.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.07%	94.00%

Plants that contains it

• Heliomeris longifolia
• Tithonia longiradiata

Cross-Links

• PubChem: 162994362
• LOTUS: LTS0227531
• wikiData: Q105267872