[(1S,2R,3R,4R,6S,8S,10S,11S)-3-hydroxy-3,8-dimethyl-2-[(Z)-2-methylbut-2-enoyl]oxy-12-methylidene-9,13-dioxo-5,14-dioxatricyclo[9.3.0.04,6]tetradecan-10-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: f1ec27a3-e311-4b46-8b86-d98347935303
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(1S,2R,3R,4R,6S,8S,10S,11S)-3-hydroxy-3,8-dimethyl-2-[(Z)-2-methylbut-2-enoyl]oxy-12-methylidene-9,13-dioxo-5,14-dioxatricyclo[9.3.0.04,6]tetradecan-10-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2C(C(C(C3C(O3)CC(C1=O)C)(C)O)OC(=O)C(=CC)C)OC(=O)C2=C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1[C@@H]2[C@@H]([C@H]([C@]([C@H]3[C@@H](O3)C[C@@H](C1=O)C)(C)O)OC(=O)/C(=C\C)/C)OC(=O)C2=C
• InChI: InChI=1S/C25H32O9/c1-8-11(3)22(27)32-18-16-14(6)24(29)33-19(16)21(34-23(28)12(4)9-2)25(7,30)20-15(31-20)10-13(5)17(18)26/h8-9,13,15-16,18-21,30H,6,10H2,1-5,7H3/b11-8-,12-9-/t13-,15-,16+,18-,19-,20+,21+,25+/m0/s1
• InChI Key: HUAHQSNQXUOCEJ-HFRMUBQDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₉
• Molecular Weight: 476.50 g/mol
• Exact Mass: 476.20463259 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 1.97
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9486	94.86%
Caco-2	-	0.6725	67.25%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5929	59.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8825	88.25%
OATP1B3 inhibitior	+	0.8701	87.01%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8447	84.47%
P-glycoprotein inhibitior	+	0.8040	80.40%
P-glycoprotein substrate	-	0.5963	59.63%
CYP3A4 substrate	+	0.6507	65.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9048	90.48%
CYP3A4 inhibition	-	0.5447	54.47%
CYP2C9 inhibition	-	0.8562	85.62%
CYP2C19 inhibition	-	0.8442	84.42%
CYP2D6 inhibition	-	0.9451	94.51%
CYP1A2 inhibition	-	0.7043	70.43%
CYP2C8 inhibition	-	0.6575	65.75%
CYP inhibitory promiscuity	-	0.8885	88.85%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Danger	0.4186	41.86%
Eye corrosion	-	0.9741	97.41%
Eye irritation	-	0.8876	88.76%
Skin irritation	-	0.6277	62.77%
Skin corrosion	-	0.8966	89.66%
Ames mutagenesis	-	0.5578	55.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.6192	61.92%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.7928	79.28%
skin sensitisation	-	0.6694	66.94%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.9090	90.90%
Acute Oral Toxicity (c)	III	0.3693	36.93%
Estrogen receptor binding	+	0.7606	76.06%
Androgen receptor binding	+	0.5584	55.84%
Thyroid receptor binding	+	0.5578	55.78%
Glucocorticoid receptor binding	+	0.7224	72.24%
Aromatase binding	+	0.5488	54.88%
PPAR gamma	+	0.6991	69.91%
Honey bee toxicity	-	0.6298	62.98%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9342	93.42%

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	96.85%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.88%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.06%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.91%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.22%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.07%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.00%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.80%	92.94%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.66%	91.07%
CHEMBL221	P23219	Cyclooxygenase-1	86.46%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.24%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	86.17%	91.19%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.51%	95.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.65%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.38%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.11%	93.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.92%	91.24%

Plants that contains it

• Inula cappa

Cross-Links

• PubChem: 163039709
• LOTUS: LTS0265012
• wikiData: Q105033703