[(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2S)-2-methyloxirane-2-carboxylate

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	bb61eb15-2931-44ca-94a8-dd8f6b1fcb50
Taxonomy	Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name	[(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2S)-2-methyloxirane-2-carboxylate
SMILES (Canonical)	CC1(CO1)C(=O)OC2CC(=C)C3CC(C(=C)C3C4C2C(=C)C(=O)O4)O
SMILES (Isomeric)	C[C@]1(CO1)C(=O)O[C@H]2CC(=C)[C@@H]3C[C@@H](C(=C)[C@@H]3[C@@H]4[C@@H]2C(=C)C(=O)O4)O
InChI	InChI=1S/C19H22O6/c1-8-5-13(24-18(22)19(4)7-23-19)15-10(3)17(21)25-16(15)14-9(2)12(20)6-11(8)14/h11-16,20H,1-3,5-7H2,4H3/t11-,12-,13-,14-,15+,16+,19-/m0/s1
InChI Key	GMSCGNDWWHJSIY-UJAQHVGQSA-N
Popularity	5 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₉H₂₂O₆
Molecular Weight	346.40 g/mol
Exact Mass	346.14163842 g/mol
Topological Polar Surface Area (TPSA)	85.40 Å²
XlogP	0.80
Atomic LogP (AlogP)	1.30
H-Bond Acceptor	6
H-Bond Donor	1
Rotatable Bonds	2

Synonyms

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There are no found synonyms.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9865	98.65%
Caco-2	-	0.6333	63.33%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6317	63.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8904	89.04%
OATP1B3 inhibitior	+	0.9554	95.54%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7444	74.44%
P-glycoprotein inhibitior	-	0.8349	83.49%
P-glycoprotein substrate	-	0.6312	63.12%
CYP3A4 substrate	+	0.6745	67.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8499	84.99%
CYP3A4 inhibition	-	0.8272	82.72%
CYP2C9 inhibition	-	0.8520	85.20%
CYP2C19 inhibition	-	0.8734	87.34%
CYP2D6 inhibition	-	0.9282	92.82%
CYP1A2 inhibition	-	0.7773	77.73%
CYP2C8 inhibition	-	0.7757	77.57%
CYP inhibitory promiscuity	-	0.9663	96.63%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5401	54.01%
Eye corrosion	-	0.9699	96.99%
Eye irritation	-	0.8200	82.00%
Skin irritation	-	0.6234	62.34%
Skin corrosion	-	0.8893	88.93%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7852	78.52%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.6992	69.92%
skin sensitisation	-	0.7307	73.07%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.7513	75.13%
Acute Oral Toxicity (c)	III	0.4311	43.11%
Estrogen receptor binding	+	0.6505	65.05%
Androgen receptor binding	+	0.6587	65.87%
Thyroid receptor binding	+	0.5579	55.79%
Glucocorticoid receptor binding	+	0.6756	67.56%
Aromatase binding	+	0.5340	53.40%
PPAR gamma	+	0.5203	52.03%
Honey bee toxicity	-	0.5606	56.06%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9688	96.88%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	95.52%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	91.32%	91.19%
CHEMBL2996	Q05655	Protein kinase C delta	90.91%	97.79%
CHEMBL221	P23219	Cyclooxygenase-1	90.50%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.48%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.33%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.10%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.46%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.10%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.39%	85.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.90%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.46%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.97%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.61%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.53%	97.25%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.26%	89.34%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.18%	93.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.07%	97.14%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.92%	96.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Centaurea cineraria subsp. cineraria

Centaurea collina

Centaurea lanigera

Psephellus bellus