(3R,3aS,6E,9R,10S,11aR)-9-hydroxy-3,6,10-trimethyl-3a,4,5,8,9,10,11,11a-octahydro-3H-cyclodeca[b]furan-2-one

Details

• Internal ID: cb29932f-5b0f-48d6-9b84-c5c06fcf79fa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3R,3aS,6E,9R,10S,11aR)-9-hydroxy-3,6,10-trimethyl-3a,4,5,8,9,10,11,11a-octahydro-3H-cyclodeca[b]furan-2-one
• SMILES (Canonical): CC1CC2C(CCC(=CCC1O)C)C(C(=O)O2)C
• SMILES (Isomeric): C[C@H]1C[C@@H]2[C@@H](CC/C(=C/C[C@H]1O)/C)[C@H](C(=O)O2)C
• InChI: InChI=1S/C15H24O3/c1-9-4-6-12-11(3)15(17)18-14(12)8-10(2)13(16)7-5-9/h5,10-14,16H,4,6-8H2,1-3H3/b9-5+/t10-,11+,12-,13+,14+/m0/s1
• InChI Key: LAOQYXNUSDEVJK-HZIUKEMISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.35 g/mol
• Exact Mass: 252.17254462 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.68
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9971	99.71%
Caco-2	+	0.8162	81.62%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6173	61.73%
OATP2B1 inhibitior	-	0.8527	85.27%
OATP1B1 inhibitior	+	0.9533	95.33%
OATP1B3 inhibitior	+	0.9583	95.83%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.8922	89.22%
P-glycoprotein inhibitior	-	0.9307	93.07%
P-glycoprotein substrate	-	0.8325	83.25%
CYP3A4 substrate	+	0.5614	56.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8313	83.13%
CYP3A4 inhibition	-	0.6555	65.55%
CYP2C9 inhibition	-	0.9401	94.01%
CYP2C19 inhibition	-	0.8827	88.27%
CYP2D6 inhibition	-	0.9523	95.23%
CYP1A2 inhibition	-	0.5056	50.56%
CYP2C8 inhibition	-	0.9057	90.57%
CYP inhibitory promiscuity	-	0.9558	95.58%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6045	60.45%
Eye corrosion	-	0.9703	97.03%
Eye irritation	-	0.9673	96.73%
Skin irritation	+	0.5480	54.80%
Skin corrosion	-	0.9375	93.75%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6198	61.98%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.7283	72.83%
skin sensitisation	-	0.6372	63.72%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.5839	58.39%
Acute Oral Toxicity (c)	III	0.4281	42.81%
Estrogen receptor binding	-	0.7947	79.47%
Androgen receptor binding	+	0.5705	57.05%
Thyroid receptor binding	-	0.5455	54.55%
Glucocorticoid receptor binding	+	0.5953	59.53%
Aromatase binding	-	0.8729	87.29%
PPAR gamma	-	0.8351	83.51%
Honey bee toxicity	-	0.8756	87.56%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9595	95.95%

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	94.06%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.57%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.04%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.69%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.74%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.43%	94.80%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.45%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.35%	89.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	82.37%	86.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.80%	85.14%

Plants that contains it

• Artemisia absinthium
• Artemisia campestris

Cross-Links

• PubChem: 101808627
• LOTUS: LTS0118590
• wikiData: Q105148811