[(1S,2R,4S,6R,8S,9S,11R)-8,9-dihydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.04,6]tetradecan-2-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 4b082a0b-5c32-434a-bc2b-0857af6624d0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(1S,2R,4S,6R,8S,9S,11R)-8,9-dihydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.04,6]tetradecan-2-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC2(C(O2)CC(C(CC3C1C(=C)C(=O)O3)(C)O)O)C
• SMILES (Isomeric): C/C=C(/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)(C)O)O)C
• InChI: InChI=1S/C20H28O7/c1-6-10(2)17(22)25-13-9-20(5)15(27-20)7-14(21)19(4,24)8-12-16(13)11(3)18(23)26-12/h6,12-16,21,24H,3,7-9H2,1-2,4-5H3/b10-6-/t12-,13-,14+,15-,16+,19+,20+/m1/s1
• InChI Key: OFNWVOIJEOVYPP-CFUPXWRKSA-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: 1.50
• Atomic LogP (AlogP): 1.42
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9705	97.05%
Caco-2	+	0.5149	51.49%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5976	59.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8960	89.60%
OATP1B3 inhibitior	+	0.9006	90.06%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7507	75.07%
P-glycoprotein inhibitior	-	0.6544	65.44%
P-glycoprotein substrate	-	0.6224	62.24%
CYP3A4 substrate	+	0.6744	67.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8803	88.03%
CYP3A4 inhibition	+	0.5522	55.22%
CYP2C9 inhibition	-	0.7887	78.87%
CYP2C19 inhibition	-	0.8182	81.82%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.6815	68.15%
CYP2C8 inhibition	-	0.7190	71.90%
CYP inhibitory promiscuity	-	0.9773	97.73%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5217	52.17%
Eye corrosion	-	0.9829	98.29%
Eye irritation	-	0.9424	94.24%
Skin irritation	-	0.5746	57.46%
Skin corrosion	-	0.9142	91.42%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4011	40.11%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.6908	69.08%
skin sensitisation	-	0.7808	78.08%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.8559	85.59%
Acute Oral Toxicity (c)	III	0.3517	35.17%
Estrogen receptor binding	+	0.7940	79.40%
Androgen receptor binding	+	0.6005	60.05%
Thyroid receptor binding	+	0.5946	59.46%
Glucocorticoid receptor binding	+	0.7424	74.24%
Aromatase binding	+	0.5864	58.64%
PPAR gamma	+	0.6156	61.56%
Honey bee toxicity	-	0.5889	58.89%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9899	98.99%

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	97.30%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	94.64%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.52%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	91.02%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.76%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.79%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.87%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.49%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.33%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.06%	91.07%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.20%	92.94%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.93%	91.24%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.56%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.13%	95.50%
CHEMBL2996	Q05655	Protein kinase C delta	82.29%	97.79%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.27%	93.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.25%	97.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.51%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.34%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.31%	85.14%

Plants that contains it

• Helianthus annuus
• Helianthus argophyllus

Cross-Links

• PubChem: 162851648
• LOTUS: LTS0254910
• wikiData: Q105191307