3-[2-(1,3-dihydroxy-2,5,5,8a-tetramethyl-4-oxo-2,3,4a,6,7,8-hexahydronaphthalen-1-yl)ethyl]-2-hydroxy-2H-furan-5-one

Details

• Internal ID: 565bd3b5-3051-48a4-94d3-e54107ebaf46
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: 3-[2-(1,3-dihydroxy-2,5,5,8a-tetramethyl-4-oxo-2,3,4a,6,7,8-hexahydronaphthalen-1-yl)ethyl]-2-hydroxy-2H-furan-5-one
• SMILES (Canonical): CC1C(C(=O)C2C(CCCC2(C1(CCC3=CC(=O)OC3O)O)C)(C)C)O
• SMILES (Isomeric): CC1C(C(=O)C2C(CCCC2(C1(CCC3=CC(=O)OC3O)O)C)(C)C)O
• InChI: InChI=1S/C20H30O6/c1-11-14(22)15(23)16-18(2,3)7-5-8-19(16,4)20(11,25)9-6-12-10-13(21)26-17(12)24/h10-11,14,16-17,22,24-25H,5-9H2,1-4H3
• InChI Key: ORLJFXGZZYWOIF-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₆
• Molecular Weight: 366.40 g/mol
• Exact Mass: 366.20423867 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.71
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9737	97.37%
Caco-2	-	0.5438	54.38%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7166	71.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7920	79.20%
OATP1B3 inhibitior	+	0.8765	87.65%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5782	57.82%
BSEP inhibitior	+	0.6070	60.70%
P-glycoprotein inhibitior	-	0.7569	75.69%
P-glycoprotein substrate	-	0.7122	71.22%
CYP3A4 substrate	+	0.5884	58.84%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8939	89.39%
CYP3A4 inhibition	-	0.5523	55.23%
CYP2C9 inhibition	-	0.8239	82.39%
CYP2C19 inhibition	-	0.8286	82.86%
CYP2D6 inhibition	-	0.9507	95.07%
CYP1A2 inhibition	-	0.8847	88.47%
CYP2C8 inhibition	-	0.7844	78.44%
CYP inhibitory promiscuity	-	0.8674	86.74%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5487	54.87%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.9291	92.91%
Skin irritation	+	0.6457	64.57%
Skin corrosion	-	0.9155	91.55%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6830	68.30%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.5179	51.79%
skin sensitisation	-	0.8147	81.47%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.7426	74.26%
Acute Oral Toxicity (c)	I	0.6610	66.10%
Estrogen receptor binding	+	0.8879	88.79%
Androgen receptor binding	+	0.6490	64.90%
Thyroid receptor binding	+	0.6667	66.67%
Glucocorticoid receptor binding	+	0.8174	81.74%
Aromatase binding	+	0.7666	76.66%
PPAR gamma	-	0.5237	52.37%
Honey bee toxicity	-	0.8596	85.96%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9920	99.20%

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	98.57%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.49%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.45%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.06%	85.14%
CHEMBL2581	P07339	Cathepsin D	91.36%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.88%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.26%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.07%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.02%	100.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.47%	86.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.85%	95.89%

Plants that contains it

• Leonurus sibiricus

Cross-Links

• PubChem: 73803386
• LOTUS: LTS0229222
• wikiData: Q105198032