(8,9-diacetyloxy-4-hydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl) 3-methylbutanoate

Details

• Internal ID: d3ecac09-1576-4d32-9bda-12f359b6a9b5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: (8,9-diacetyloxy-4-hydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl) 3-methylbutanoate
• SMILES (Canonical): CC1C2C(CC(C2(C(C3C(C1O)OC(=O)C3=C)OC(=O)C)C)OC(=O)C)OC(=O)CC(C)C
• SMILES (Isomeric): CC1C2C(CC(C2(C(C3C(C1O)OC(=O)C3=C)OC(=O)C)C)OC(=O)C)OC(=O)CC(C)C
• InChI: InChI=1S/C24H34O9/c1-10(2)8-17(27)32-15-9-16(30-13(5)25)24(7)19(15)12(4)20(28)21-18(11(3)23(29)33-21)22(24)31-14(6)26/h10,12,15-16,18-22,28H,3,8-9H2,1-2,4-7H3
• InChI Key: OHXAYESXJHEHGM-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₄O₉
• Molecular Weight: 466.50 g/mol
• Exact Mass: 466.22028266 g/mol
• Topological Polar Surface Area (TPSA): 125.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 1.94
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9817	98.17%
Caco-2	-	0.7110	71.10%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5926	59.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8364	83.64%
OATP1B3 inhibitior	-	0.3571	35.71%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5903	59.03%
P-glycoprotein inhibitior	+	0.6553	65.53%
P-glycoprotein substrate	+	0.5235	52.35%
CYP3A4 substrate	+	0.6605	66.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	-	0.6447	64.47%
CYP2C9 inhibition	-	0.7674	76.74%
CYP2C19 inhibition	-	0.7579	75.79%
CYP2D6 inhibition	-	0.9499	94.99%
CYP1A2 inhibition	-	0.6441	64.41%
CYP2C8 inhibition	-	0.6908	69.08%
CYP inhibitory promiscuity	-	0.9273	92.73%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5740	57.40%
Eye corrosion	-	0.9781	97.81%
Eye irritation	-	0.8724	87.24%
Skin irritation	-	0.5730	57.30%
Skin corrosion	-	0.9160	91.60%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7028	70.28%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.5677	56.77%
skin sensitisation	-	0.6155	61.55%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.7311	73.11%
Acute Oral Toxicity (c)	III	0.3855	38.55%
Estrogen receptor binding	+	0.7957	79.57%
Androgen receptor binding	+	0.6159	61.59%
Thyroid receptor binding	+	0.5406	54.06%
Glucocorticoid receptor binding	+	0.6446	64.46%
Aromatase binding	+	0.6141	61.41%
PPAR gamma	+	0.6254	62.54%
Honey bee toxicity	-	0.6689	66.89%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9884	98.84%

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	97.60%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	96.37%	97.79%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.86%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.77%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.67%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	94.93%	90.17%
CHEMBL2581	P07339	Cathepsin D	89.85%	98.95%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.20%	96.47%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.08%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.62%	97.25%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.55%	91.07%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.62%	89.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.85%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.27%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.13%	99.23%
CHEMBL299	P17252	Protein kinase C alpha	83.13%	98.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.35%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	81.72%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.58%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.54%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.81%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.48%	95.89%

Plants that contains it

• Gaillardia pulchella

Cross-Links

• PubChem: 162872004
• LOTUS: LTS0253506
• wikiData: Q105192352