[(3R,3aS,4R,5E,7S,9E,11aS)-4-hydroxy-3,6,10-trimethyl-2-oxo-3a,4,7,8,11,11a-hexahydro-3H-cyclodeca[b]furan-7-yl] acetate

Details

• Internal ID: ebf2c752-ea30-4466-bea9-e28173a06dcf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3R,3aS,4R,5E,7S,9E,11aS)-4-hydroxy-3,6,10-trimethyl-2-oxo-3a,4,7,8,11,11a-hexahydro-3H-cyclodeca[b]furan-7-yl] acetate
• SMILES (Canonical): CC1C2C(CC(=CCC(C(=CC2O)C)OC(=O)C)C)OC1=O
• SMILES (Isomeric): C[C@@H]1[C@@H]2[C@H](C/C(=C/C[C@@H](/C(=C/[C@H]2O)/C)OC(=O)C)/C)OC1=O
• InChI: InChI=1S/C17H24O5/c1-9-5-6-14(21-12(4)18)10(2)8-13(19)16-11(3)17(20)22-15(16)7-9/h5,8,11,13-16,19H,6-7H2,1-4H3/b9-5+,10-8+/t11-,13-,14+,15+,16+/m1/s1
• InChI Key: LCWPLRGURNGJEW-QKVUXTHMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₅
• Molecular Weight: 308.40 g/mol
• Exact Mass: 308.16237386 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.14
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9831	98.31%
Caco-2	+	0.6486	64.86%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6132	61.32%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.9248	92.48%
OATP1B3 inhibitior	+	0.9212	92.12%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7451	74.51%
P-glycoprotein inhibitior	-	0.7680	76.80%
P-glycoprotein substrate	-	0.7455	74.55%
CYP3A4 substrate	+	0.5826	58.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8517	85.17%
CYP3A4 inhibition	-	0.6825	68.25%
CYP2C9 inhibition	-	0.8557	85.57%
CYP2C19 inhibition	-	0.8542	85.42%
CYP2D6 inhibition	-	0.9537	95.37%
CYP1A2 inhibition	+	0.5425	54.25%
CYP2C8 inhibition	-	0.8317	83.17%
CYP inhibitory promiscuity	-	0.8808	88.08%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5016	50.16%
Eye corrosion	-	0.9634	96.34%
Eye irritation	-	0.9548	95.48%
Skin irritation	-	0.5697	56.97%
Skin corrosion	-	0.9300	93.00%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5582	55.82%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.7119	71.19%
skin sensitisation	-	0.7910	79.10%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.8919	89.19%
Acute Oral Toxicity (c)	II	0.4258	42.58%
Estrogen receptor binding	+	0.5384	53.84%
Androgen receptor binding	-	0.6826	68.26%
Thyroid receptor binding	-	0.6841	68.41%
Glucocorticoid receptor binding	+	0.5769	57.69%
Aromatase binding	-	0.7887	78.87%
PPAR gamma	-	0.5961	59.61%
Honey bee toxicity	-	0.7470	74.70%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6850	68.50%
Fish aquatic toxicity	+	0.9811	98.11%

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	95.79%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.56%	97.25%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.67%	94.80%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.67%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.14%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.51%	89.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	84.42%	86.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.53%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.52%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	82.14%	94.73%

Plants that contains it

• Helianthus californicus

Cross-Links

• PubChem: 163009198
• LOTUS: LTS0237689
• wikiData: Q105150033