(1S,4aR,5S,8aR)-5-[(2-methoxy-3-methyl-5-oxofuran-2-yl)methyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid

Details

• Internal ID: b3cb2691-2b18-4409-a5ff-c12a2e6403c8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1S,4aR,5S,8aR)-5-[(2-methoxy-3-methyl-5-oxofuran-2-yl)methyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• InChI: InChI=1S/C21H30O5/c1-13-7-8-16-19(3,9-6-10-20(16,4)18(23)24)15(13)12-21(25-5)14(2)11-17(22)26-21/h11,15-16H,1,6-10,12H2,2-5H3,(H,23,24)/t15-,16+,19+,20-,21?/m0/s1
• InChI Key: YHCCJHREGRTSPV-IGONYFHZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₅
• Molecular Weight: 362.50 g/mol
• Exact Mass: 362.20932405 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 4.09
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9854	98.54%
Caco-2	+	0.7276	72.76%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7324	73.24%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7679	76.79%
OATP1B3 inhibitior	-	0.4142	41.42%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6053	60.53%
BSEP inhibitior	+	0.7877	78.77%
P-glycoprotein inhibitior	-	0.5216	52.16%
P-glycoprotein substrate	-	0.7654	76.54%
CYP3A4 substrate	+	0.6762	67.62%
CYP2C9 substrate	-	0.8047	80.47%
CYP2D6 substrate	-	0.9049	90.49%
CYP3A4 inhibition	-	0.5067	50.67%
CYP2C9 inhibition	-	0.7584	75.84%
CYP2C19 inhibition	-	0.7878	78.78%
CYP2D6 inhibition	-	0.9602	96.02%
CYP1A2 inhibition	-	0.5455	54.55%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.8369	83.69%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6297	62.97%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.8659	86.59%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9281	92.81%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6864	68.64%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6354	63.54%
skin sensitisation	-	0.8532	85.32%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.4648	46.48%
Acute Oral Toxicity (c)	I	0.3077	30.77%
Estrogen receptor binding	+	0.7329	73.29%
Androgen receptor binding	+	0.6662	66.62%
Thyroid receptor binding	+	0.6971	69.71%
Glucocorticoid receptor binding	+	0.8567	85.67%
Aromatase binding	+	0.7761	77.61%
PPAR gamma	+	0.6266	62.66%
Honey bee toxicity	-	0.8881	88.81%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9962	99.62%

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	96.80%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	96.45%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.44%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.46%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.47%	94.45%
CHEMBL2581	P07339	Cathepsin D	87.07%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.19%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.46%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.13%	91.07%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.11%	96.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.36%	92.62%

Plants that contains it

• Platycladus orientalis

Cross-Links

• PubChem: 101027921
• LOTUS: LTS0228629
• wikiData: Q105348350