(3S,3aS,4R,5E,9E,11aS)-4-hydroxy-3-(hydroxymethyl)-6,10-dimethyl-3a,4,7,8,11,11a-hexahydro-3H-cyclodeca[b]furan-2-one

Details

• Internal ID: 35cbd075-8655-4f51-b4a2-08bec7b5aa80
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3S,3aS,4R,5E,9E,11aS)-4-hydroxy-3-(hydroxymethyl)-6,10-dimethyl-3a,4,7,8,11,11a-hexahydro-3H-cyclodeca[b]furan-2-one
• SMILES (Canonical): CC1=CC(C2C(CC(=CCC1)C)OC(=O)C2CO)O
• SMILES (Isomeric): C/C/1=C\[C@H]([C@H]2[C@H](C/C(=C/CC1)/C)OC(=O)[C@@H]2CO)O
• InChI: InChI=1S/C15H22O4/c1-9-4-3-5-10(2)7-13-14(12(17)6-9)11(8-16)15(18)19-13/h5-6,11-14,16-17H,3-4,7-8H2,1-2H3/b9-6+,10-5+/t11-,12-,13+,14+/m1/s1
• InChI Key: QVJUFUFXXCEYBS-SAMKRSAWSA-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: 1.30
• 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	+	0.9734	97.34%
Caco-2	+	0.6792	67.92%
Blood Brain Barrier	+	0.6428	64.28%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6759	67.59%
OATP2B1 inhibitior	-	0.8546	85.46%
OATP1B1 inhibitior	+	0.9408	94.08%
OATP1B3 inhibitior	+	0.9632	96.32%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6067	60.67%
BSEP inhibitior	-	0.8262	82.62%
P-glycoprotein inhibitior	-	0.9394	93.94%
P-glycoprotein substrate	-	0.9080	90.80%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8410	84.10%
CYP3A4 inhibition	-	0.6104	61.04%
CYP2C9 inhibition	-	0.9192	91.92%
CYP2C19 inhibition	-	0.8914	89.14%
CYP2D6 inhibition	-	0.8994	89.94%
CYP1A2 inhibition	+	0.5470	54.70%
CYP2C8 inhibition	-	0.8931	89.31%
CYP inhibitory promiscuity	-	0.8501	85.01%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6328	63.28%
Eye corrosion	-	0.9833	98.33%
Eye irritation	-	0.9255	92.55%
Skin irritation	-	0.5734	57.34%
Skin corrosion	-	0.9490	94.90%
Ames mutagenesis	-	0.5091	50.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.6282	62.82%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.5585	55.85%
skin sensitisation	-	0.8700	87.00%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.8853	88.53%
Acute Oral Toxicity (c)	III	0.4811	48.11%
Estrogen receptor binding	-	0.7250	72.50%
Androgen receptor binding	-	0.5665	56.65%
Thyroid receptor binding	-	0.7048	70.48%
Glucocorticoid receptor binding	+	0.5488	54.88%
Aromatase binding	-	0.8271	82.71%
PPAR gamma	-	0.6223	62.23%
Honey bee toxicity	-	0.8827	88.27%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9546	95.46%

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	94.20%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.74%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.63%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.80%	97.09%
CHEMBL2581	P07339	Cathepsin D	86.99%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.13%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.22%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.50%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	80.68%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.27%	86.33%

Plants that contains it

• Tanacetopsis mucronata

Cross-Links

• PubChem: 163049005
• LOTUS: LTS0257459
• wikiData: Q105228698