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

Details

• Internal ID: d5eafffb-dcd5-45a5-8a58-33e80c11f434
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[[(2R)-3-methyl-5-oxo-2H-furan-2-yl]methyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC1=CC(=O)OC1CC2C(=C)CCC3C2(CCCC3(C)C(=O)O)C
• SMILES (Isomeric): CC1=CC(=O)O[C@@H]1C[C@H]2C(=C)CC[C@@H]3[C@@]2(CCC[C@]3(C)C(=O)O)C
• InChI: InChI=1S/C20H28O4/c1-12-6-7-16-19(3,8-5-9-20(16,4)18(22)23)14(12)11-15-13(2)10-17(21)24-15/h10,14-16H,1,5-9,11H2,2-4H3,(H,22,23)/t14-,15+,16+,19+,20-/m0/s1
• InChI Key: RZOJUNXETNSSSH-AFJOWOCMSA-N
• Popularity: 1 reference 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: 3.60
• Atomic LogP (AlogP): 4.11
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9873	98.73%
Caco-2	+	0.7004	70.04%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7719	77.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7506	75.06%
OATP1B3 inhibitior	-	0.3022	30.22%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5303	53.03%
BSEP inhibitior	+	0.5792	57.92%
P-glycoprotein inhibitior	-	0.5743	57.43%
P-glycoprotein substrate	-	0.7927	79.27%
CYP3A4 substrate	+	0.6454	64.54%
CYP2C9 substrate	-	0.8074	80.74%
CYP2D6 substrate	-	0.9179	91.79%
CYP3A4 inhibition	+	0.5804	58.04%
CYP2C9 inhibition	-	0.8861	88.61%
CYP2C19 inhibition	-	0.8490	84.90%
CYP2D6 inhibition	-	0.9533	95.33%
CYP1A2 inhibition	-	0.6707	67.07%
CYP2C8 inhibition	-	0.7297	72.97%
CYP inhibitory promiscuity	-	0.8738	87.38%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6421	64.21%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.8897	88.97%
Skin irritation	+	0.6337	63.37%
Skin corrosion	-	0.9093	90.93%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7020	70.20%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.6389	63.89%
skin sensitisation	-	0.7661	76.61%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.6548	65.48%
Acute Oral Toxicity (c)	III	0.6266	62.66%
Estrogen receptor binding	+	0.7519	75.19%
Androgen receptor binding	+	0.5613	56.13%
Thyroid receptor binding	+	0.6879	68.79%
Glucocorticoid receptor binding	+	0.8750	87.50%
Aromatase binding	+	0.6801	68.01%
PPAR gamma	+	0.5663	56.63%
Honey bee toxicity	-	0.9322	93.22%
Biodegradation	-	0.6750	67.50%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.16%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.46%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.50%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.05%	99.23%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.17%	96.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.33%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.13%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.56%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.62%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.60%	97.09%

Plants that contains it

• Thuja standishii

Cross-Links

• PubChem: 71551590
• LOTUS: LTS0148083
• wikiData: Q105248490