(2S)-3-[(E)-2-[(1R,3S,4aS,8aS)-3-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: 4ba4d167-badc-4961-9ed4-4b9f742e739a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (2S)-3-[(E)-2-[(1R,3S,4aS,8aS)-3-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/c1-12-14(7-6-13-10-17(22)24-18(13)23)20(4)9-5-8-19(2,3)16(20)11-15(12)21/h6-7,10,14-16,18,21,23H,1,5,8-9,11H2,2-4H3/b7-6+/t14-,15-,16-,18-,20+/m0/s1
• InChI Key: GHNHHZAECXQMOM-WXQGCQCLSA-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: 3.10
• 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	+	0.9921	99.21%
Caco-2	-	0.5623	56.23%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6254	62.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8347	83.47%
OATP1B3 inhibitior	-	0.2306	23.06%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.6988	69.88%
P-glycoprotein inhibitior	-	0.8522	85.22%
P-glycoprotein substrate	-	0.7781	77.81%
CYP3A4 substrate	+	0.6425	64.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8888	88.88%
CYP3A4 inhibition	-	0.5743	57.43%
CYP2C9 inhibition	-	0.9010	90.10%
CYP2C19 inhibition	-	0.8758	87.58%
CYP2D6 inhibition	-	0.9523	95.23%
CYP1A2 inhibition	-	0.6840	68.40%
CYP2C8 inhibition	-	0.6931	69.31%
CYP inhibitory promiscuity	-	0.9209	92.09%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5328	53.28%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9350	93.50%
Skin irritation	+	0.6258	62.58%
Skin corrosion	-	0.9150	91.50%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4251	42.51%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.5823	58.23%
skin sensitisation	-	0.6665	66.65%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.6242	62.42%
Acute Oral Toxicity (c)	I	0.7577	75.77%
Estrogen receptor binding	+	0.7552	75.52%
Androgen receptor binding	+	0.5693	56.93%
Thyroid receptor binding	+	0.5995	59.95%
Glucocorticoid receptor binding	+	0.7222	72.22%
Aromatase binding	+	0.6520	65.20%
PPAR gamma	+	0.7759	77.59%
Honey bee toxicity	-	0.7839	78.39%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9954	99.54%

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	97.01%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.84%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	91.06%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.55%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.36%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.06%	89.00%
CHEMBL2581	P07339	Cathepsin D	85.03%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.96%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.01%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.87%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.69%	99.23%
CHEMBL1977	P11473	Vitamin D receptor	81.50%	99.43%

Plants that contains it

• Hedychium gardnerianum

Cross-Links

• PubChem: 163185135
• LOTUS: LTS0273960
• wikiData: Q105008625