(3aS,5S,6E,10E,11aR)-5-hydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one

Details

• Internal ID: b2bc9f62-e369-4e7f-9799-8dccf6e0561a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aS,5S,6E,10E,11aR)-5-hydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1=CC2C(CC(C(=CCC1)C)O)C(=C)C(=O)O2
• SMILES (Isomeric): C/C/1=C\[C@@H]2[C@@H](C[C@@H](/C(=C/CC1)/C)O)C(=C)C(=O)O2
• InChI: InChI=1S/C15H20O3/c1-9-5-4-6-10(2)13(16)8-12-11(3)15(17)18-14(12)7-9/h6-7,12-14,16H,3-5,8H2,1-2H3/b9-7+,10-6+/t12-,13-,14+/m0/s1
• InChI Key: CHKPFVHCBRAVJP-MHCGRXEOSA-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: 1.00
• Atomic LogP (AlogP): 2.52
• 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	+	0.9929	99.29%
Caco-2	+	0.8480	84.80%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5310	53.10%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.9253	92.53%
OATP1B3 inhibitior	+	0.9307	93.07%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.8999	89.99%
P-glycoprotein inhibitior	-	0.9009	90.09%
P-glycoprotein substrate	-	0.9277	92.77%
CYP3A4 substrate	+	0.5347	53.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	-	0.7390	73.90%
CYP2C9 inhibition	-	0.9369	93.69%
CYP2C19 inhibition	-	0.8496	84.96%
CYP2D6 inhibition	-	0.9304	93.04%
CYP1A2 inhibition	+	0.5873	58.73%
CYP2C8 inhibition	-	0.7965	79.65%
CYP inhibitory promiscuity	-	0.9340	93.40%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5948	59.48%
Eye corrosion	-	0.9613	96.13%
Eye irritation	-	0.8840	88.40%
Skin irritation	+	0.5469	54.69%
Skin corrosion	-	0.8733	87.33%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7410	74.10%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.8250	82.50%
skin sensitisation	-	0.5699	56.99%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6310	63.10%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.4505	45.05%
Acute Oral Toxicity (c)	III	0.5004	50.04%
Estrogen receptor binding	+	0.5512	55.12%
Androgen receptor binding	-	0.6677	66.77%
Thyroid receptor binding	-	0.6444	64.44%
Glucocorticoid receptor binding	+	0.7778	77.78%
Aromatase binding	-	0.6928	69.28%
PPAR gamma	-	0.5301	53.01%
Honey bee toxicity	-	0.8408	84.08%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9509	95.09%

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	93.97%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.74%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.05%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.07%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.34%	93.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.30%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.79%	95.50%
CHEMBL2581	P07339	Cathepsin D	82.19%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.16%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.64%	100.00%

Plants that contains it

• Inula helenium
• Pluchea dioscoridis

Cross-Links

• PubChem: 13817190
• LOTUS: LTS0130547
• wikiData: Q104958975