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

Details

• Internal ID: 49217bd1-1b76-4c47-98fd-4ad4dd60fccd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3S,3aR,4S,6E,10E,11aR)-4-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one
• SMILES (Canonical): CC1C2C(CC(=CCCC(=CC2OC1=O)C)CO)O
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](C/C(=C\CC/C(=C/[C@H]2OC1=O)/C)/CO)O
• InChI: InChI=1S/C15H22O4/c1-9-4-3-5-11(8-16)7-12(17)14-10(2)15(18)19-13(14)6-9/h5-6,10,12-14,16-17H,3-4,7-8H2,1-2H3/b9-6+,11-5+/t10-,12-,13+,14+/m0/s1
• InChI Key: AACJDWCUEJRPLO-RYLXDPBVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.57
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9845	98.45%
Caco-2	+	0.6360	63.60%
Blood Brain Barrier	+	0.5784	57.84%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7077	70.77%
OATP2B1 inhibitior	-	0.8571	85.71%
OATP1B1 inhibitior	+	0.9069	90.69%
OATP1B3 inhibitior	+	0.9670	96.70%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6031	60.31%
BSEP inhibitior	-	0.8567	85.67%
P-glycoprotein inhibitior	-	0.9392	93.92%
P-glycoprotein substrate	-	0.8160	81.60%
CYP3A4 substrate	+	0.5550	55.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8410	84.10%
CYP3A4 inhibition	-	0.5299	52.99%
CYP2C9 inhibition	-	0.9329	93.29%
CYP2C19 inhibition	-	0.9073	90.73%
CYP2D6 inhibition	-	0.9134	91.34%
CYP1A2 inhibition	-	0.6069	60.69%
CYP2C8 inhibition	-	0.9167	91.67%
CYP inhibitory promiscuity	-	0.9062	90.62%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6525	65.25%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9486	94.86%
Skin irritation	-	0.6077	60.77%
Skin corrosion	-	0.9529	95.29%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7892	78.92%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.5449	54.49%
skin sensitisation	-	0.8910	89.10%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.4898	48.98%
Acute Oral Toxicity (c)	III	0.4053	40.53%
Estrogen receptor binding	-	0.6033	60.33%
Androgen receptor binding	-	0.6573	65.73%
Thyroid receptor binding	-	0.7234	72.34%
Glucocorticoid receptor binding	-	0.4943	49.43%
Aromatase binding	-	0.8516	85.16%
PPAR gamma	-	0.7199	71.99%
Honey bee toxicity	-	0.8841	88.41%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9440	94.40%

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	93.16%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.45%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.02%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.79%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.11%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.29%	100.00%
CHEMBL4208	P20618	Proteasome component C5	83.32%	90.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	83.29%	86.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.72%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.15%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	80.17%	94.73%

Plants that contains it

• Seriphidium fragrans
• Seriphidium gypsaceum

Cross-Links

• PubChem: 14335242
• LOTUS: LTS0203353
• wikiData: Q104907819