3-[(4,7-dimethyl-1-oxo-4,4a,5,6,7,7a-hexahydro-3H-cyclopenta[c]pyran-3-yl)oxy]-3,4,7-trimethyl-4,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-one

Details

• Internal ID: 59605e12-dd0f-40d9-ab78-a6002ce3069e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 3-[(4,7-dimethyl-1-oxo-4,4a,5,6,7,7a-hexahydro-3H-cyclopenta[c]pyran-3-yl)oxy]-3,4,7-trimethyl-4,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-one
• SMILES (Canonical): CC1CCC2C1C(=O)OC(C2C)OC3(C(C4CCC(C4C(=O)O3)C)C)C
• SMILES (Isomeric): CC1CCC2C1C(=O)OC(C2C)OC3(C(C4CCC(C4C(=O)O3)C)C)C
• InChI: InChI=1S/C21H32O5/c1-10-6-8-14-12(3)20(24-18(22)16(10)14)26-21(5)13(4)15-9-7-11(2)17(15)19(23)25-21/h10-17,20H,6-9H2,1-5H3
• InChI Key: HXFBSJZTEMCZFX-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₅
• Molecular Weight: 364.50 g/mol
• Exact Mass: 364.22497412 g/mol
• Topological Polar Surface Area (TPSA): 61.80 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 3.76
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9372	93.72%
Caco-2	+	0.5065	50.65%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5684	56.84%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.9239	92.39%
OATP1B3 inhibitior	+	0.9595	95.95%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.7689	76.89%
P-glycoprotein inhibitior	-	0.5220	52.20%
P-glycoprotein substrate	-	0.7585	75.85%
CYP3A4 substrate	+	0.6161	61.61%
CYP2C9 substrate	-	0.6039	60.39%
CYP2D6 substrate	-	0.8464	84.64%
CYP3A4 inhibition	-	0.7635	76.35%
CYP2C9 inhibition	-	0.8675	86.75%
CYP2C19 inhibition	-	0.9223	92.23%
CYP2D6 inhibition	-	0.9570	95.70%
CYP1A2 inhibition	-	0.6011	60.11%
CYP2C8 inhibition	-	0.8268	82.68%
CYP inhibitory promiscuity	-	0.9224	92.24%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6077	60.77%
Eye corrosion	-	0.9658	96.58%
Eye irritation	-	0.8986	89.86%
Skin irritation	-	0.5708	57.08%
Skin corrosion	-	0.7177	71.77%
Ames mutagenesis	-	0.6391	63.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.7087	70.87%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.6951	69.51%
skin sensitisation	-	0.8603	86.03%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.7357	73.57%
Acute Oral Toxicity (c)	III	0.5556	55.56%
Estrogen receptor binding	+	0.7867	78.67%
Androgen receptor binding	+	0.7160	71.60%
Thyroid receptor binding	+	0.5915	59.15%
Glucocorticoid receptor binding	+	0.6245	62.45%
Aromatase binding	+	0.5645	56.45%
PPAR gamma	+	0.6255	62.55%
Honey bee toxicity	-	0.7572	75.72%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9264	92.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4481	P35228	Nitric oxide synthase, inducible	93.49%	94.80%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.47%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.34%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.48%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.64%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.47%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	82.68%	92.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.82%	99.23%
CHEMBL1871	P10275	Androgen Receptor	80.57%	96.43%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.53%	97.25%

Plants that contains it

• Nepeta cataria

Cross-Links

• PubChem: 5320122
• NPASS: NPC124485