[(3aR,4R,5S,5aS,6S,8R,8aR,9R,9aS)-8-acetyloxy-4,9-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: 7404f0c2-9645-4aa5-8db9-76e7e806226a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: [(3aR,4R,5S,5aS,6S,8R,8aR,9R,9aS)-8-acetyloxy-4,9-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)O)C)OC(=O)C)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)O)C)OC(=O)C)OC(=O)C(C)C
• InChI: InChI=1S/C21H30O8/c1-8(2)19(25)28-12-7-13(27-11(5)22)21(6)15(12)10(4)16(23)17-14(18(21)24)9(3)20(26)29-17/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: WCNVDQPMAWLKJN-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	+	0.9583	95.83%
Caco-2	-	0.7038	70.38%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6050	60.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8814	88.14%
OATP1B3 inhibitior	+	0.8677	86.77%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9122	91.22%
P-glycoprotein inhibitior	-	0.5648	56.48%
P-glycoprotein substrate	-	0.6523	65.23%
CYP3A4 substrate	+	0.6547	65.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8873	88.73%
CYP3A4 inhibition	-	0.7448	74.48%
CYP2C9 inhibition	-	0.7952	79.52%
CYP2C19 inhibition	-	0.7676	76.76%
CYP2D6 inhibition	-	0.9298	92.98%
CYP1A2 inhibition	-	0.6914	69.14%
CYP2C8 inhibition	-	0.7374	73.74%
CYP inhibitory promiscuity	-	0.8639	86.39%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4905	49.05%
Eye corrosion	-	0.9755	97.55%
Eye irritation	-	0.8639	86.39%
Skin irritation	-	0.5991	59.91%
Skin corrosion	-	0.8828	88.28%
Ames mutagenesis	-	0.5664	56.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.5590	55.90%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.5710	57.10%
skin sensitisation	-	0.6696	66.96%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.6513	65.13%
Acute Oral Toxicity (c)	III	0.3681	36.81%
Estrogen receptor binding	+	0.7799	77.99%
Androgen receptor binding	+	0.5605	56.05%
Thyroid receptor binding	+	0.5995	59.95%
Glucocorticoid receptor binding	+	0.5698	56.98%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6123	61.23%
Honey bee toxicity	-	0.5691	56.91%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9643	96.43%

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	98.03%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.55%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	96.04%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.38%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.22%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.26%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	89.34%	97.79%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.28%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.00%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.96%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	86.54%	91.19%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.95%	96.47%
CHEMBL2581	P07339	Cathepsin D	85.08%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.73%	96.77%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	84.44%	95.71%
CHEMBL299	P17252	Protein kinase C alpha	83.14%	98.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.09%	95.56%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.36%	89.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.22%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.21%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.91%	97.14%

Plants that contains it

• Gaillardia pulchella

Cross-Links

• PubChem: 162950900
• LOTUS: LTS0276281
• wikiData: Q105244937