(3aS,6E,10E,11aS)-6-(hydroxymethyl)-10-methyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one

Details

• Internal ID: e3556081-884e-4134-b84e-7ea0a64b621e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aS,6E,10E,11aS)-6-(hydroxymethyl)-10-methyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1=CC2C(CCC(=CCC1)CO)C(=C)C(=O)O2
• SMILES (Isomeric): C/C/1=C\[C@H]2[C@@H](CC/C(=C\CC1)/CO)C(=C)C(=O)O2
• InChI: InChI=1S/C15H20O3/c1-10-4-3-5-12(9-16)6-7-13-11(2)15(17)18-14(13)8-10/h5,8,13-14,16H,2-4,6-7,9H2,1H3/b10-8+,12-5+/t13-,14-/m0/s1
• InChI Key: CSWGBLVUKVWCOS-DDSAIHNYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 2.52
• H-Bond Acceptor: 3
• 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	+	0.9942	99.42%
Caco-2	+	0.8064	80.64%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6322	63.22%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.9230	92.30%
OATP1B3 inhibitior	+	0.9512	95.12%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	-	0.5673	56.73%
BSEP inhibitior	-	0.8488	84.88%
P-glycoprotein inhibitior	-	0.8588	85.88%
P-glycoprotein substrate	-	0.9075	90.75%
CYP3A4 substrate	+	0.5425	54.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8440	84.40%
CYP3A4 inhibition	-	0.8033	80.33%
CYP2C9 inhibition	-	0.7811	78.11%
CYP2C19 inhibition	-	0.7089	70.89%
CYP2D6 inhibition	-	0.8820	88.20%
CYP1A2 inhibition	+	0.5745	57.45%
CYP2C8 inhibition	-	0.7856	78.56%
CYP inhibitory promiscuity	-	0.8083	80.83%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6595	65.95%
Eye corrosion	-	0.9371	93.71%
Eye irritation	-	0.6161	61.61%
Skin irritation	-	0.6428	64.28%
Skin corrosion	-	0.9223	92.23%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6357	63.57%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.7191	71.91%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6151	61.51%
Acute Oral Toxicity (c)	III	0.5404	54.04%
Estrogen receptor binding	-	0.6847	68.47%
Androgen receptor binding	-	0.5457	54.57%
Thyroid receptor binding	-	0.6815	68.15%
Glucocorticoid receptor binding	+	0.6384	63.84%
Aromatase binding	-	0.7446	74.46%
PPAR gamma	-	0.6827	68.27%
Honey bee toxicity	-	0.9026	90.26%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9866	98.66%

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	93.71%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.69%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.02%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	90.29%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.91%	97.09%
CHEMBL2581	P07339	Cathepsin D	88.59%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.95%	100.00%
CHEMBL4208	P20618	Proteasome component C5	81.58%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.40%	96.09%

Plants that contains it

• Clibadium surinamense

Cross-Links

• PubChem: 162919809
• LOTUS: LTS0162936
• wikiData: Q104969625