(1R,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[2-(5-oxo-2H-furan-4-yl)ethyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid

Details

• Internal ID: a4e6c1a1-976f-4814-8530-8e1c88194622
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1R,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[2-(5-oxo-2H-furan-4-yl)ethyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC12CCCC(C1CCC(=C)C2CCC3=CCOC3=O)(C)C(=O)O
• SMILES (Isomeric): C[C@]12CCC[C@@]([C@@H]1CCC(=C)[C@@H]2CCC3=CCOC3=O)(C)C(=O)O
• InChI: InChI=1S/C20H28O4/c1-13-5-8-16-19(2,10-4-11-20(16,3)18(22)23)15(13)7-6-14-9-12-24-17(14)21/h9,15-16H,1,4-8,10-12H2,2-3H3,(H,22,23)/t15-,16+,19+,20+/m0/s1
• InChI Key: FHQSDRHZGCMBKG-LNKGRISISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 4.11
• H-Bond Acceptor: 3
• 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	+	0.9862	98.62%
Caco-2	+	0.6956	69.56%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7930	79.30%
OATP2B1 inhibitior	-	0.8660	86.60%
OATP1B1 inhibitior	+	0.8034	80.34%
OATP1B3 inhibitior	+	0.9153	91.53%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.5660	56.60%
BSEP inhibitior	+	0.6275	62.75%
P-glycoprotein inhibitior	-	0.6067	60.67%
P-glycoprotein substrate	-	0.7614	76.14%
CYP3A4 substrate	+	0.6352	63.52%
CYP2C9 substrate	-	0.8074	80.74%
CYP2D6 substrate	-	0.9179	91.79%
CYP3A4 inhibition	-	0.5413	54.13%
CYP2C9 inhibition	-	0.7634	76.34%
CYP2C19 inhibition	-	0.8319	83.19%
CYP2D6 inhibition	-	0.9093	90.93%
CYP1A2 inhibition	-	0.6810	68.10%
CYP2C8 inhibition	-	0.6593	65.93%
CYP inhibitory promiscuity	-	0.8394	83.94%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6412	64.12%
Eye corrosion	-	0.9830	98.30%
Eye irritation	-	0.7737	77.37%
Skin irritation	-	0.5362	53.62%
Skin corrosion	-	0.9333	93.33%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4798	47.98%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5615	56.15%
skin sensitisation	-	0.7710	77.10%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.5170	51.70%
Acute Oral Toxicity (c)	III	0.6469	64.69%
Estrogen receptor binding	+	0.6673	66.73%
Androgen receptor binding	+	0.6441	64.41%
Thyroid receptor binding	+	0.7164	71.64%
Glucocorticoid receptor binding	+	0.8292	82.92%
Aromatase binding	+	0.6808	68.08%
PPAR gamma	+	0.5295	52.95%
Honey bee toxicity	-	0.9126	91.26%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	97.08%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.48%	97.25%
CHEMBL2581	P07339	Cathepsin D	91.69%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.98%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.99%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.41%	99.23%
CHEMBL4040	P28482	MAP kinase ERK2	84.32%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.65%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	82.03%	91.19%
CHEMBL5028	O14672	ADAM10	81.33%	97.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.94%	100.00%

Plants that contains it

• Acanthostyles buniifolius
• Brickellia lemmonii
• Gutierrezia sarothrae

Cross-Links

• PubChem: 26112947
• LOTUS: LTS0087820
• wikiData: Q104397000