(3S,3aS,6Z,10E,11aS)-6-(hydroxymethyl)-3,10-dimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one

Details

• Internal ID: 77f24e1c-9fa0-48fc-abe4-8fc6235c30d2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3S,3aS,6Z,10E,11aS)-6-(hydroxymethyl)-3,10-dimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one
• SMILES (Canonical): CC1C2CCC(=CCCC(=CC2OC1=O)C)CO
• SMILES (Isomeric): C[C@H]1[C@@H]2CC/C(=C/CC/C(=C/[C@H]2OC1=O)/C)/CO
• InChI: InChI=1S/C15H22O3/c1-10-4-3-5-12(9-16)6-7-13-11(2)15(17)18-14(13)8-10/h5,8,11,13-14,16H,3-4,6-7,9H2,1-2H3/b10-8+,12-5-/t11-,13-,14+/m0/s1
• InChI Key: HFQLMAXPTJTMQQ-BOSKEESHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.60
• 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	+	0.9935	99.35%
Caco-2	+	0.8763	87.63%
Blood Brain Barrier	-	0.5145	51.45%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6833	68.33%
OATP2B1 inhibitior	-	0.8544	85.44%
OATP1B1 inhibitior	+	0.9248	92.48%
OATP1B3 inhibitior	+	0.9560	95.60%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.5923	59.23%
BSEP inhibitior	-	0.8266	82.66%
P-glycoprotein inhibitior	-	0.9211	92.11%
P-glycoprotein substrate	-	0.8460	84.60%
CYP3A4 substrate	+	0.5458	54.58%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8497	84.97%
CYP3A4 inhibition	-	0.6003	60.03%
CYP2C9 inhibition	-	0.7846	78.46%
CYP2C19 inhibition	-	0.7837	78.37%
CYP2D6 inhibition	-	0.8568	85.68%
CYP1A2 inhibition	+	0.6284	62.84%
CYP2C8 inhibition	-	0.9158	91.58%
CYP inhibitory promiscuity	-	0.7733	77.33%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6487	64.87%
Eye corrosion	-	0.9671	96.71%
Eye irritation	-	0.8366	83.66%
Skin irritation	-	0.6498	64.98%
Skin corrosion	-	0.9420	94.20%
Ames mutagenesis	-	0.6278	62.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.6156	61.56%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.7212	72.12%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.6576	65.76%
Acute Oral Toxicity (c)	III	0.5171	51.71%
Estrogen receptor binding	-	0.5877	58.77%
Androgen receptor binding	-	0.5859	58.59%
Thyroid receptor binding	-	0.6497	64.97%
Glucocorticoid receptor binding	+	0.5877	58.77%
Aromatase binding	-	0.8424	84.24%
PPAR gamma	-	0.6989	69.89%
Honey bee toxicity	-	0.9030	90.30%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9789	97.89%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.43%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.89%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.78%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.32%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.78%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.41%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.00%	97.09%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	85.22%	86.00%
CHEMBL2581	P07339	Cathepsin D	84.97%	98.95%
CHEMBL1871	P10275	Androgen Receptor	83.94%	96.43%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.51%	94.80%

Plants that contains it

• Inula helenium

Cross-Links

• PubChem: 163039356
• LOTUS: LTS0110616
• wikiData: Q105027467