(3aR,5Z,8R,9E,11aS)-8-hydroxy-6-(hydroxymethyl)-10-methyl-3-methylidene-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-2-one

Details

• Internal ID: b7215128-f4ce-4c8f-a776-c26fe371d69f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aR,5Z,8R,9E,11aS)-8-hydroxy-6-(hydroxymethyl)-10-methyl-3-methylidene-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-2-one
• InChI: InChI=1S/C15H20O4/c1-9-5-12(17)7-11(8-16)3-4-13-10(2)15(18)19-14(13)6-9/h3,5,12-14,16-17H,2,4,6-8H2,1H3/b9-5+,11-3-/t12-,13+,14-/m0/s1
• InChI Key: VYHNGQAYWSAIMN-SBASVFFCSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.49
• 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	+	0.9813	98.13%
Caco-2	+	0.6594	65.94%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6423	64.23%
OATP2B1 inhibitior	-	0.8557	85.57%
OATP1B1 inhibitior	+	0.8663	86.63%
OATP1B3 inhibitior	+	0.9605	96.05%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9060	90.60%
P-glycoprotein inhibitior	-	0.8834	88.34%
P-glycoprotein substrate	-	0.8604	86.04%
CYP3A4 substrate	+	0.5430	54.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8359	83.59%
CYP3A4 inhibition	-	0.8059	80.59%
CYP2C9 inhibition	-	0.9044	90.44%
CYP2C19 inhibition	-	0.8628	86.28%
CYP2D6 inhibition	-	0.9339	93.39%
CYP1A2 inhibition	-	0.7855	78.55%
CYP2C8 inhibition	-	0.7771	77.71%
CYP inhibitory promiscuity	-	0.8782	87.82%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6376	63.76%
Eye corrosion	-	0.9814	98.14%
Eye irritation	-	0.7864	78.64%
Skin irritation	-	0.6894	68.94%
Skin corrosion	-	0.9316	93.16%
Ames mutagenesis	-	0.5354	53.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4930	49.30%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.6175	61.75%
skin sensitisation	-	0.8011	80.11%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.7831	78.31%
Acute Oral Toxicity (c)	III	0.5587	55.87%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.5660	56.60%
Thyroid receptor binding	-	0.7079	70.79%
Glucocorticoid receptor binding	+	0.6474	64.74%
Aromatase binding	-	0.6532	65.32%
PPAR gamma	-	0.6527	65.27%
Honey bee toxicity	-	0.8672	86.72%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9615	96.15%

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	92.22%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.18%	91.11%
CHEMBL2581	P07339	Cathepsin D	88.98%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.90%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	85.78%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.84%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.96%	96.09%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.33%	96.37%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.22%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.11%	93.03%
CHEMBL4208	P20618	Proteasome component C5	80.02%	90.00%

Plants that contains it

• Arctotis aspera

Cross-Links

• PubChem: 162866064
• LOTUS: LTS0034367
• wikiData: Q105298992