[(3aR,8S,8aS,9R,9aR)-8-acetyloxy-5,8a-dimethyl-1-methylidene-2-oxo-4,6,7,8,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-9-yl] 2-methylpropanoate

Details

• Internal ID: 7778411b-4499-492a-8939-87e5c033ac54
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: [(3aR,8S,8aS,9R,9aR)-8-acetyloxy-5,8a-dimethyl-1-methylidene-2-oxo-4,6,7,8,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-9-yl] 2-methylpropanoate
• SMILES (Canonical): CC1=C2CCC(C2(C(C3C(C1)OC(=O)C3=C)OC(=O)C(C)C)C)OC(=O)C
• SMILES (Isomeric): CC1=C2CC[C@@H]([C@]2([C@@H]([C@H]3[C@@H](C1)OC(=O)C3=C)OC(=O)C(C)C)C)OC(=O)C
• InChI: InChI=1S/C21H28O6/c1-10(2)19(23)27-18-17-12(4)20(24)26-15(17)9-11(3)14-7-8-16(21(14,18)6)25-13(5)22/h10,15-18H,4,7-9H2,1-3,5-6H3/t15-,16+,17-,18-,21+/m1/s1
• InChI Key: QZMGWKYDRYCVCR-KSZKVXGTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₆
• Molecular Weight: 376.40 g/mol
• Exact Mass: 376.18858861 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.10
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9888	98.88%
Caco-2	+	0.6623	66.23%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6751	67.51%
OATP2B1 inhibitior	-	0.8613	86.13%
OATP1B1 inhibitior	+	0.8737	87.37%
OATP1B3 inhibitior	-	0.3449	34.49%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.7795	77.95%
P-glycoprotein inhibitior	+	0.5780	57.80%
P-glycoprotein substrate	-	0.7900	79.00%
CYP3A4 substrate	+	0.6562	65.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8935	89.35%
CYP3A4 inhibition	-	0.7188	71.88%
CYP2C9 inhibition	-	0.6551	65.51%
CYP2C19 inhibition	-	0.7179	71.79%
CYP2D6 inhibition	-	0.9504	95.04%
CYP1A2 inhibition	+	0.6819	68.19%
CYP2C8 inhibition	-	0.5644	56.44%
CYP inhibitory promiscuity	-	0.9257	92.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6070	60.70%
Eye corrosion	-	0.9736	97.36%
Eye irritation	-	0.7505	75.05%
Skin irritation	-	0.5115	51.15%
Skin corrosion	-	0.9004	90.04%
Ames mutagenesis	-	0.5564	55.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.4556	45.56%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.6210	62.10%
skin sensitisation	-	0.7129	71.29%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.8931	89.31%
Acute Oral Toxicity (c)	III	0.4652	46.52%
Estrogen receptor binding	+	0.8109	81.09%
Androgen receptor binding	+	0.6343	63.43%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7021	70.21%
Aromatase binding	-	0.6214	62.14%
PPAR gamma	+	0.6930	69.30%
Honey bee toxicity	-	0.6524	65.24%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9966	99.66%

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	96.21%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.92%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.91%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.86%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.82%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.34%	85.14%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.24%	96.47%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.04%	97.25%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.20%	98.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.85%	95.50%
CHEMBL2581	P07339	Cathepsin D	86.37%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	86.33%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.87%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.96%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.10%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.31%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.78%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.60%	93.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.66%	93.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.37%	100.00%
CHEMBL5028	O14672	ADAM10	81.14%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	80.27%	90.17%

Plants that contains it

• Wedelia grandiflora

Cross-Links

• PubChem: 163023041
• LOTUS: LTS0099324
• wikiData: Q105232166