[(3aR,4R,6R,6aR,9aR,9bR)-6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-methylpropanoate

Details

• Internal ID: d85eaa6f-44b9-4901-89f2-8265c7d981a9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(3aR,4R,6R,6aR,9aR,9bR)-6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-methylpropanoate
• SMILES (Canonical): CC1=CCC2C1C3C(C(CC2(C)O)OC(=O)C(C)C)C(=C)C(=O)O3
• SMILES (Isomeric): CC1=CC[C@@H]2[C@H]1[C@@H]3[C@@H]([C@@H](C[C@@]2(C)O)OC(=O)C(C)C)C(=C)C(=O)O3
• InChI: InChI=1S/C19H26O5/c1-9(2)17(20)23-13-8-19(5,22)12-7-6-10(3)14(12)16-15(13)11(4)18(21)24-16/h6,9,12-16,22H,4,7-8H2,1-3,5H3/t12-,13-,14+,15-,16-,19-/m1/s1
• InChI Key: SLWRMDVPXSTKON-WLQXYJQWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₆O₅
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.17802393 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.39
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9902	99.02%
Caco-2	+	0.6334	63.34%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6004	60.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9185	91.85%
OATP1B3 inhibitior	+	0.8452	84.52%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9647	96.47%
P-glycoprotein inhibitior	-	0.6565	65.65%
P-glycoprotein substrate	-	0.7537	75.37%
CYP3A4 substrate	+	0.6440	64.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8958	89.58%
CYP3A4 inhibition	+	0.5298	52.98%
CYP2C9 inhibition	-	0.7301	73.01%
CYP2C19 inhibition	-	0.8160	81.60%
CYP2D6 inhibition	-	0.9585	95.85%
CYP1A2 inhibition	-	0.6936	69.36%
CYP2C8 inhibition	-	0.7237	72.37%
CYP inhibitory promiscuity	-	0.9520	95.20%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5563	55.63%
Eye corrosion	-	0.9762	97.62%
Eye irritation	-	0.9216	92.16%
Skin irritation	-	0.5672	56.72%
Skin corrosion	-	0.9010	90.10%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5415	54.15%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.6691	66.91%
skin sensitisation	-	0.6625	66.25%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.5224	52.24%
Acute Oral Toxicity (c)	II	0.4136	41.36%
Estrogen receptor binding	+	0.7847	78.47%
Androgen receptor binding	+	0.6936	69.36%
Thyroid receptor binding	+	0.5831	58.31%
Glucocorticoid receptor binding	+	0.6100	61.00%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.5695	56.95%
Honey bee toxicity	-	0.6499	64.99%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9912	99.12%

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	95.63%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.53%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	94.94%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.91%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.98%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.48%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.02%	86.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.67%	96.47%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.14%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.30%	97.09%
CHEMBL230	P35354	Cyclooxygenase-2	85.01%	89.63%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.78%	91.07%
CHEMBL2581	P07339	Cathepsin D	84.52%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.74%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.02%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	81.58%	97.79%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.11%	85.30%
CHEMBL3401	O75469	Pregnane X receptor	80.88%	94.73%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.46%	93.03%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.40%	95.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.27%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.11%	100.00%

Plants that contains it

• Tithonia diversifolia

Cross-Links

• PubChem: 102120568
• LOTUS: LTS0052981
• wikiData: Q105255707