4-[(1S)-2-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-1-hydroxyethyl]-2H-furan-5-one

Details

• Internal ID: dc514fdc-b992-4928-a525-8a5b4e9e0388
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: 4-[(1S)-2-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-1-hydroxyethyl]-2H-furan-5-one
• SMILES (Canonical): CC1CCC2(C(C1(C)CC(C3=CCOC3=O)O)CCC=C2C)C
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)C[C@@H](C3=CCOC3=O)O)CCC=C2C)C
• InChI: InChI=1S/C20H30O3/c1-13-6-5-7-17-19(13,3)10-8-14(2)20(17,4)12-16(21)15-9-11-23-18(15)22/h6,9,14,16-17,21H,5,7-8,10-12H2,1-4H3/t14-,16+,17+,19+,20+/m1/s1
• InChI Key: KWTXYVRTXYEKJE-GVJFSJSTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.21949481 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.02
• 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	+	0.9946	99.46%
Caco-2	+	0.7940	79.40%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6899	68.99%
OATP2B1 inhibitior	-	0.8649	86.49%
OATP1B1 inhibitior	+	0.9184	91.84%
OATP1B3 inhibitior	+	0.9759	97.59%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	+	0.5683	56.83%
BSEP inhibitior	+	0.7053	70.53%
P-glycoprotein inhibitior	-	0.7665	76.65%
P-glycoprotein substrate	-	0.8652	86.52%
CYP3A4 substrate	+	0.6052	60.52%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.8757	87.57%
CYP3A4 inhibition	-	0.7184	71.84%
CYP2C9 inhibition	-	0.8533	85.33%
CYP2C19 inhibition	-	0.8118	81.18%
CYP2D6 inhibition	-	0.9454	94.54%
CYP1A2 inhibition	-	0.7775	77.75%
CYP2C8 inhibition	-	0.7577	75.77%
CYP inhibitory promiscuity	-	0.8558	85.58%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5139	51.39%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9660	96.60%
Skin irritation	+	0.6425	64.25%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	-	0.7766	77.66%
Human Ether-a-go-go-Related Gene inhibition	+	0.6675	66.75%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.6387	63.87%
skin sensitisation	-	0.8294	82.94%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.5810	58.10%
Acute Oral Toxicity (c)	III	0.5832	58.32%
Estrogen receptor binding	+	0.5769	57.69%
Androgen receptor binding	+	0.5709	57.09%
Thyroid receptor binding	+	0.6631	66.31%
Glucocorticoid receptor binding	+	0.7184	71.84%
Aromatase binding	+	0.5655	56.55%
PPAR gamma	+	0.5431	54.31%
Honey bee toxicity	-	0.8611	86.11%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9833	98.33%

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	97.89%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.79%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.67%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.51%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.23%	97.09%
CHEMBL2581	P07339	Cathepsin D	89.67%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.46%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.12%	89.00%
CHEMBL4208	P20618	Proteasome component C5	80.85%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.39%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.15%	95.89%

Plants that contains it

• Callicarpa americana

Cross-Links

• PubChem: 16115036
• LOTUS: LTS0210731
• wikiData: Q105147104