(4aR,5S,6R,8aS)-5,6,8a-trimethyl-5-[[(2S)-3-methyl-5-oxo-2H-furan-2-yl]methyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

Details

• Internal ID: e4d45b7d-005a-4abf-9cbb-7c25e2faef06
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (4aR,5S,6R,8aS)-5,6,8a-trimethyl-5-[[(2S)-3-methyl-5-oxo-2H-furan-2-yl]methyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid
• InChI: InChI=1S/C20H28O4/c1-12-10-17(21)24-15(12)11-20(4)13(2)8-9-19(3)14(18(22)23)6-5-7-16(19)20/h6,10,13,15-16H,5,7-9,11H2,1-4H3,(H,22,23)/t13-,15+,16+,19-,20+/m1/s1
• InChI Key: AEPFBSNEBUKEMX-NPACWLSJSA-N
• Popularity: 2 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: 4.40
• 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	+	0.9853	98.53%
Caco-2	+	0.8270	82.70%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7506	75.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8718	87.18%
OATP1B3 inhibitior	+	0.9105	91.05%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5771	57.71%
BSEP inhibitior	+	0.5523	55.23%
P-glycoprotein inhibitior	-	0.5897	58.97%
P-glycoprotein substrate	-	0.8297	82.97%
CYP3A4 substrate	+	0.5888	58.88%
CYP2C9 substrate	-	0.8074	80.74%
CYP2D6 substrate	-	0.9179	91.79%
CYP3A4 inhibition	-	0.5280	52.80%
CYP2C9 inhibition	-	0.9333	93.33%
CYP2C19 inhibition	-	0.9228	92.28%
CYP2D6 inhibition	-	0.9468	94.68%
CYP1A2 inhibition	-	0.6155	61.55%
CYP2C8 inhibition	-	0.7026	70.26%
CYP inhibitory promiscuity	-	0.8569	85.69%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5920	59.20%
Eye corrosion	-	0.9944	99.44%
Eye irritation	-	0.9706	97.06%
Skin irritation	+	0.6877	68.77%
Skin corrosion	-	0.9032	90.32%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7163	71.63%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5138	51.38%
skin sensitisation	-	0.7815	78.15%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.5121	51.21%
Acute Oral Toxicity (c)	III	0.7083	70.83%
Estrogen receptor binding	+	0.7565	75.65%
Androgen receptor binding	-	0.5393	53.93%
Thyroid receptor binding	+	0.7049	70.49%
Glucocorticoid receptor binding	+	0.8465	84.65%
Aromatase binding	+	0.7402	74.02%
PPAR gamma	+	0.5854	58.54%
Honey bee toxicity	-	0.9175	91.75%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9953	99.53%

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	94.25%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.51%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.50%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.38%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.93%	99.23%
CHEMBL2581	P07339	Cathepsin D	86.54%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.45%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.75%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.07%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.93%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.19%	86.33%

Plants that contains it

• Dendrobium comatum

Cross-Links

• PubChem: 162908986
• LOTUS: LTS0148829
• wikiData: Q104910314