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

Details

• Internal ID: d7a19c7b-8dbb-4e3a-bf3b-d79230bc2d6d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: 3-[2-[(1S,2R,4S,4aR,7R,8aR)-4,7-dihydroxy-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]ethyl]-2H-furan-5-one
• InChI: InChI=1S/C20H30O4/c1-12-8-17(22)20(4)13(2)7-15(21)10-16(20)19(12,3)6-5-14-9-18(23)24-11-14/h9,12,15-17,21-22H,2,5-8,10-11H2,1,3-4H3/t12-,15+,16-,17+,19+,20+/m1/s1
• InChI Key: KVNYIQMJQBEPJT-NHJWICSWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.99
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9855	98.55%
Caco-2	+	0.6000	60.00%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7086	70.86%
OATP2B1 inhibitior	-	0.8646	86.46%
OATP1B1 inhibitior	+	0.8634	86.34%
OATP1B3 inhibitior	+	0.9499	94.99%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5042	50.42%
BSEP inhibitior	-	0.5669	56.69%
P-glycoprotein inhibitior	-	0.6766	67.66%
P-glycoprotein substrate	+	0.5270	52.70%
CYP3A4 substrate	+	0.6401	64.01%
CYP2C9 substrate	-	0.7970	79.70%
CYP2D6 substrate	-	0.8987	89.87%
CYP3A4 inhibition	+	0.5618	56.18%
CYP2C9 inhibition	-	0.9170	91.70%
CYP2C19 inhibition	-	0.8902	89.02%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.7950	79.50%
CYP2C8 inhibition	-	0.7637	76.37%
CYP inhibitory promiscuity	-	0.8254	82.54%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5753	57.53%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8121	81.21%
Skin irritation	+	0.6752	67.52%
Skin corrosion	-	0.9407	94.07%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3768	37.68%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.6917	69.17%
skin sensitisation	-	0.8426	84.26%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.5631	56.31%
Acute Oral Toxicity (c)	III	0.6900	69.00%
Estrogen receptor binding	+	0.6834	68.34%
Androgen receptor binding	+	0.6761	67.61%
Thyroid receptor binding	+	0.6657	66.57%
Glucocorticoid receptor binding	+	0.7972	79.72%
Aromatase binding	+	0.7972	79.72%
PPAR gamma	-	0.6333	63.33%
Honey bee toxicity	-	0.7323	73.23%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9944	99.44%

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	96.03%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.05%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	93.37%	95.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.28%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.56%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.91%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.88%	100.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	88.59%	86.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.91%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.78%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.54%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.10%	97.09%
CHEMBL255	P29275	Adenosine A2b receptor	82.22%	98.59%

Plants that contains it

• Scutellaria drummondii

Cross-Links

• PubChem: 101681757
• LOTUS: LTS0225859
• wikiData: Q105146634