3-[(1R,4aS,7S,7aR)-4,7-dimethyl-3-(3-methylbutanoyl)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl]-4-methoxy-5-methylchromen-2-one

Details

• Internal ID: 8e7088bb-42b7-4f5d-9d2d-928c99e1283b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 3-[(1R,4aS,7S,7aR)-4,7-dimethyl-3-(3-methylbutanoyl)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl]-4-methoxy-5-methylchromen-2-one
• SMILES (Canonical): CC1CCC2C1C(OC(=C2C)C(=O)CC(C)C)C3=C(C4=C(C=CC=C4OC3=O)C)OC
• SMILES (Isomeric): C[C@H]1CC[C@H]2[C@@H]1[C@@H](OC(=C2C)C(=O)CC(C)C)C3=C(C4=C(C=CC=C4OC3=O)C)OC
• InChI: InChI=1S/C26H32O5/c1-13(2)12-18(27)23-16(5)17-11-10-15(4)20(17)25(31-23)22-24(29-6)21-14(3)8-7-9-19(21)30-26(22)28/h7-9,13,15,17,20,25H,10-12H2,1-6H3/t15-,17+,20+,25+/m0/s1
• InChI Key: KQGAIGDLVVMDTI-BWIYXDQASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₅
• Molecular Weight: 424.50 g/mol
• Exact Mass: 424.22497412 g/mol
• Topological Polar Surface Area (TPSA): 61.80 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.73
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9865	98.65%
Caco-2	+	0.7786	77.86%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7620	76.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8955	89.55%
OATP1B3 inhibitior	+	0.8328	83.28%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9223	92.23%
P-glycoprotein inhibitior	+	0.8617	86.17%
P-glycoprotein substrate	+	0.5319	53.19%
CYP3A4 substrate	+	0.6219	62.19%
CYP2C9 substrate	-	0.5518	55.18%
CYP2D6 substrate	-	0.8617	86.17%
CYP3A4 inhibition	-	0.5416	54.16%
CYP2C9 inhibition	-	0.5834	58.34%
CYP2C19 inhibition	+	0.5199	51.99%
CYP2D6 inhibition	-	0.8695	86.95%
CYP1A2 inhibition	-	0.5892	58.92%
CYP2C8 inhibition	+	0.4882	48.82%
CYP inhibitory promiscuity	+	0.6665	66.65%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5841	58.41%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.8530	85.30%
Skin irritation	-	0.7862	78.62%
Skin corrosion	-	0.9389	93.89%
Ames mutagenesis	-	0.6528	65.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.6427	64.27%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.6176	61.76%
skin sensitisation	-	0.8166	81.66%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.9015	90.15%
Acute Oral Toxicity (c)	I	0.3577	35.77%
Estrogen receptor binding	+	0.7212	72.12%
Androgen receptor binding	+	0.7334	73.34%
Thyroid receptor binding	+	0.5305	53.05%
Glucocorticoid receptor binding	+	0.8073	80.73%
Aromatase binding	+	0.5683	56.83%
PPAR gamma	+	0.7686	76.86%
Honey bee toxicity	-	0.8080	80.80%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9933	99.33%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.68%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.87%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.39%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.21%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.52%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.41%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.48%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.05%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.89%	94.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.63%	93.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.36%	94.80%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.60%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.63%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	84.47%	91.19%
CHEMBL2535	P11166	Glucose transporter	83.26%	98.75%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.53%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.30%	99.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.02%	96.77%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.66%	93.65%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.59%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.52%	96.00%
CHEMBL4040	P28482	MAP kinase ERK2	80.32%	83.82%
CHEMBL3401	O75469	Pregnane X receptor	80.13%	94.73%

Plants that contains it

• Lycoseris triplinervia

Cross-Links

• PubChem: 162963333
• LOTUS: LTS0202598
• wikiData: Q105314172