[(3aR,4R,5S,5aS,6S,8R,8aS,9R,9aS)-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] (2R)-2-methylbutanoate

Details

• Internal ID: 1355fbe2-fabd-44c0-a51c-a5cd64d46684
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: [(3aR,4R,5S,5aS,6S,8R,8aS,9R,9aS)-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] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CC(C2(C1C(C(C3C(C2OC(=O)C)C(=C)C(=O)O3)O)C)C)OC(=O)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@H]1C[C@H]([C@@]2([C@@H]1[C@@H]([C@H]([C@H]3[C@H]([C@H]2OC(=O)C)C(=C)C(=O)O3)O)C)C)OC(=O)C
• InChI: InChI=1S/C24H34O9/c1-8-10(2)22(28)32-15-9-16(30-13(5)25)24(7)18(15)12(4)19(27)20-17(11(3)23(29)33-20)21(24)31-14(6)26/h10,12,15-21,27H,3,8-9H2,1-2,4-7H3/t10-,12+,15+,16-,17-,18-,19-,20-,21-,24-/m1/s1
• InChI Key: XDFDCJAYELYDTM-KAXFTFLPSA-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: 2.90
• 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	+	0.9877	98.77%
Caco-2	-	0.6870	68.70%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.4503	45.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8405	84.05%
OATP1B3 inhibitior	+	0.8255	82.55%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5534	55.34%
P-glycoprotein inhibitior	+	0.6479	64.79%
P-glycoprotein substrate	-	0.5394	53.94%
CYP3A4 substrate	+	0.6468	64.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	+	0.5077	50.77%
CYP2C9 inhibition	-	0.8037	80.37%
CYP2C19 inhibition	-	0.7482	74.82%
CYP2D6 inhibition	-	0.9531	95.31%
CYP1A2 inhibition	-	0.6248	62.48%
CYP2C8 inhibition	-	0.6458	64.58%
CYP inhibitory promiscuity	-	0.8871	88.71%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5202	52.02%
Eye corrosion	-	0.9760	97.60%
Eye irritation	-	0.8790	87.90%
Skin irritation	-	0.5387	53.87%
Skin corrosion	-	0.8917	89.17%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7548	75.48%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.6052	60.52%
skin sensitisation	-	0.6419	64.19%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.4831	48.31%
Acute Oral Toxicity (c)	III	0.4133	41.33%
Estrogen receptor binding	+	0.8346	83.46%
Androgen receptor binding	+	0.6275	62.75%
Thyroid receptor binding	+	0.5297	52.97%
Glucocorticoid receptor binding	+	0.6640	66.40%
Aromatase binding	+	0.6165	61.65%
PPAR gamma	+	0.6591	65.91%
Honey bee toxicity	-	0.6922	69.22%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9787	97.87%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.34%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	96.99%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.72%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.48%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.18%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	95.84%	90.17%
CHEMBL2581	P07339	Cathepsin D	92.01%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.68%	85.14%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.72%	96.47%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.20%	86.33%
CHEMBL299	P17252	Protein kinase C alpha	86.53%	98.03%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.18%	89.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.46%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.04%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.26%	99.23%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.81%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.18%	89.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.18%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.13%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.68%	91.07%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.01%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	80.88%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.43%	95.89%

Plants that contains it

• Gaillardia pulchella

Cross-Links

• PubChem: 162894968
• LOTUS: LTS0123625
• wikiData: Q105325677