(2R)-3-[(E)-2-[(1S,4R,4aS,8aR)-4-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-2-hydroxy-2H-furan-5-one

Details

• Internal ID: c4ee5bd6-0f1b-4304-b017-2d5320915d03
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (2R)-3-[(E)-2-[(1S,4R,4aS,8aR)-4-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-2-hydroxy-2H-furan-5-one
• InChI: InChI=1S/C20H28O4/c1-12-10-15(21)17-19(2,3)8-5-9-20(17,4)14(12)7-6-13-11-16(22)24-18(13)23/h6-7,11,14-15,17-18,21,23H,1,5,8-10H2,2-4H3/b7-6+/t14-,15+,17-,18+,20+/m0/s1
• InChI Key: LTDSIMVYGJFVGS-INZQESPASA-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): 66.80 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.11
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9879	98.79%
Caco-2	-	0.5743	57.43%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6075	60.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7015	70.15%
OATP1B3 inhibitior	+	0.8052	80.52%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.7107	71.07%
P-glycoprotein inhibitior	-	0.8433	84.33%
P-glycoprotein substrate	-	0.7365	73.65%
CYP3A4 substrate	+	0.6330	63.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8888	88.88%
CYP3A4 inhibition	-	0.6566	65.66%
CYP2C9 inhibition	-	0.8905	89.05%
CYP2C19 inhibition	-	0.8445	84.45%
CYP2D6 inhibition	-	0.9427	94.27%
CYP1A2 inhibition	-	0.6624	66.24%
CYP2C8 inhibition	-	0.7564	75.64%
CYP inhibitory promiscuity	-	0.8646	86.46%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4960	49.60%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9603	96.03%
Skin irritation	+	0.6458	64.58%
Skin corrosion	-	0.8814	88.14%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4197	41.97%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5533	55.33%
skin sensitisation	-	0.6566	65.66%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.5761	57.61%
Acute Oral Toxicity (c)	I	0.6832	68.32%
Estrogen receptor binding	+	0.8023	80.23%
Androgen receptor binding	+	0.5588	55.88%
Thyroid receptor binding	+	0.6693	66.93%
Glucocorticoid receptor binding	+	0.8079	80.79%
Aromatase binding	+	0.7911	79.11%
PPAR gamma	+	0.7709	77.09%
Honey bee toxicity	-	0.8102	81.02%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9898	98.98%

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	98.15%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.89%	97.25%
CHEMBL2581	P07339	Cathepsin D	89.61%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.17%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.20%	100.00%
CHEMBL325	Q13547	Histone deacetylase 1	87.70%	95.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.58%	86.33%
CHEMBL1902	P62942	FK506-binding protein 1A	87.32%	97.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.89%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	86.39%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.12%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.92%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.51%	97.09%

Plants that contains it

• Hedychium forrestii

Cross-Links

• PubChem: 162971964
• LOTUS: LTS0082132
• wikiData: Q105156898