(2S)-3-[2-[(1R,4aR,8aS)-2,5,5,8a-tetramethyl-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one

Details

• Internal ID: 37d1fb2a-7017-4f4b-a10a-ae83e463f7ad
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (2S)-3-[2-[(1R,4aR,8aS)-2,5,5,8a-tetramethyl-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one
• SMILES (Canonical): CC1=CC(=O)C2C(CCCC2(C1CCC3=CC(=O)OC3O)C)(C)C
• SMILES (Isomeric): CC1=CC(=O)[C@H]2[C@]([C@@H]1CCC3=CC(=O)O[C@@H]3O)(CCCC2(C)C)C
• 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/h10-11,14,17-18,23H,5-9H2,1-4H3/t14-,17-,18+,20+/m1/s1
• InChI Key: DCIOTTDWBVOPEI-QKUWSGOFSA-N
• Popularity: 0 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): 63.60 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.55
• H-Bond Acceptor: 4
• 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	+	0.9898	98.98%
Caco-2	+	0.5334	53.34%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7897	78.97%
OATP2B1 inhibitior	-	0.8642	86.42%
OATP1B1 inhibitior	+	0.7711	77.11%
OATP1B3 inhibitior	-	0.3011	30.11%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.5532	55.32%
BSEP inhibitior	+	0.6561	65.61%
P-glycoprotein inhibitior	-	0.7038	70.38%
P-glycoprotein substrate	-	0.7849	78.49%
CYP3A4 substrate	+	0.6310	63.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8920	89.20%
CYP3A4 inhibition	-	0.6392	63.92%
CYP2C9 inhibition	-	0.6951	69.51%
CYP2C19 inhibition	-	0.7973	79.73%
CYP2D6 inhibition	-	0.9469	94.69%
CYP1A2 inhibition	-	0.6243	62.43%
CYP2C8 inhibition	-	0.7602	76.02%
CYP inhibitory promiscuity	-	0.7761	77.61%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5980	59.80%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9118	91.18%
Skin irritation	+	0.5588	55.88%
Skin corrosion	-	0.9170	91.70%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4104	41.04%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5638	56.38%
skin sensitisation	-	0.6829	68.29%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.6653	66.53%
Acute Oral Toxicity (c)	III	0.3985	39.85%
Estrogen receptor binding	+	0.8373	83.73%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.6950	69.50%
Glucocorticoid receptor binding	+	0.7975	79.75%
Aromatase binding	+	0.5671	56.71%
PPAR gamma	+	0.6747	67.47%
Honey bee toxicity	-	0.8919	89.19%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	96.56%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.06%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.21%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.56%	97.09%
CHEMBL1871	P10275	Androgen Receptor	89.29%	96.43%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.78%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.24%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.10%	95.89%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.77%	86.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.56%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.56%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	81.15%	95.93%

Plants that contains it

• Acritopappus confertus

Cross-Links

• PubChem: 162872285
• LOTUS: LTS0032317
• wikiData: Q104975414