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

Details

• Internal ID: 68dd5ef8-76ab-4466-8a3b-65e254d75d99
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: [(3aR,4R,5S,5aS,6S,8R,8aS,9R,9aS)-9-acetyloxy-4,8-dihydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl] 2-methylpropanoate
• SMILES (Canonical): CC1C2C(CC(C2(C(C3C(C1O)OC(=O)C3=C)OC(=O)C)C)O)OC(=O)C(C)C
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](C[C@H]([C@]2([C@@H]([C@H]3[C@H]([C@@H]1O)OC(=O)C3=C)OC(=O)C)C)O)OC(=O)C(C)C
• InChI: InChI=1S/C21H30O8/c1-8(2)19(25)28-12-7-13(23)21(6)15(12)10(4)16(24)17-14(9(3)20(26)29-17)18(21)27-11(5)22/h8,10,12-18,23-24H,3,7H2,1-2,4-6H3/t10-,12-,13+,14+,15+,16+,17+,18+,21+/m0/s1
• InChI Key: XNKSZCMCQDNEJE-GDFCBHTLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₈
• Molecular Weight: 410.50 g/mol
• Exact Mass: 410.19406791 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 0.98
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9795	97.95%
Caco-2	-	0.6576	65.76%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5483	54.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8751	87.51%
OATP1B3 inhibitior	+	0.8924	89.24%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9322	93.22%
P-glycoprotein inhibitior	-	0.5736	57.36%
P-glycoprotein substrate	-	0.5878	58.78%
CYP3A4 substrate	+	0.6454	64.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	-	0.7009	70.09%
CYP2C9 inhibition	-	0.8575	85.75%
CYP2C19 inhibition	-	0.8409	84.09%
CYP2D6 inhibition	-	0.9359	93.59%
CYP1A2 inhibition	-	0.7875	78.75%
CYP2C8 inhibition	-	0.7290	72.90%
CYP inhibitory promiscuity	-	0.9363	93.63%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4952	49.52%
Eye corrosion	-	0.9745	97.45%
Eye irritation	-	0.8837	88.37%
Skin irritation	-	0.5854	58.54%
Skin corrosion	-	0.8793	87.93%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6457	64.57%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.6363	63.63%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.7452	74.52%
Acute Oral Toxicity (c)	III	0.4063	40.63%
Estrogen receptor binding	+	0.7574	75.74%
Androgen receptor binding	+	0.6144	61.44%
Thyroid receptor binding	+	0.5798	57.98%
Glucocorticoid receptor binding	+	0.6384	63.84%
Aromatase binding	+	0.5547	55.47%
PPAR gamma	+	0.5741	57.41%
Honey bee toxicity	-	0.5596	55.96%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9441	94.41%

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	98.55%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	96.37%	90.17%
CHEMBL2996	Q05655	Protein kinase C delta	95.97%	97.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.15%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.45%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.10%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.20%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.99%	96.77%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.38%	96.47%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.91%	99.23%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	87.54%	95.71%
CHEMBL2581	P07339	Cathepsin D	87.50%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.03%	86.33%
CHEMBL299	P17252	Protein kinase C alpha	86.88%	98.03%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.18%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	85.88%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.44%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.29%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.08%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.74%	95.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.48%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.65%	95.89%
CHEMBL5028	O14672	ADAM10	80.80%	97.50%

Plants that contains it

• Gaillardia pulchella
• Helenium donianum

Cross-Links

• PubChem: 163026466
• LOTUS: LTS0259008
• wikiData: Q105331747