methyl (6E,7S,7aR)-7-hydroxy-3,7-dimethyl-6-[(3S)-3-methyl-2-oxononylidene]-1,7a-dihydrocyclopenta[c]pyran-5-carboxylate

Details

• Internal ID: c8a7c707-d020-4093-b9e4-19ff8c329dc9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: methyl (6E,7S,7aR)-7-hydroxy-3,7-dimethyl-6-[(3S)-3-methyl-2-oxononylidene]-1,7a-dihydrocyclopenta[c]pyran-5-carboxylate
• SMILES (Canonical): CCCCCCC(C)C(=O)C=C1C(=C2C=C(OCC2C1(C)O)C)C(=O)OC
• SMILES (Isomeric): CCCCCC[C@H](C)C(=O)/C=C/1\C(=C2C=C(OC[C@@H]2[C@]1(C)O)C)C(=O)OC
• InChI: InChI=1S/C22H32O5/c1-6-7-8-9-10-14(2)19(23)12-17-20(21(24)26-5)16-11-15(3)27-13-18(16)22(17,4)25/h11-12,14,18,25H,6-10,13H2,1-5H3/b17-12+/t14-,18-,22+/m0/s1
• InChI Key: ZSIVCMRKIFUXRS-ZLZRIERPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₅
• Molecular Weight: 376.50 g/mol
• Exact Mass: 376.22497412 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.87
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9901	99.01%
Caco-2	+	0.7230	72.30%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7913	79.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8797	87.97%
OATP1B3 inhibitior	+	0.9631	96.31%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.6864	68.64%
BSEP inhibitior	+	0.7508	75.08%
P-glycoprotein inhibitior	-	0.4431	44.31%
P-glycoprotein substrate	+	0.5983	59.83%
CYP3A4 substrate	+	0.6510	65.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9048	90.48%
CYP3A4 inhibition	-	0.7251	72.51%
CYP2C9 inhibition	-	0.7814	78.14%
CYP2C19 inhibition	-	0.8745	87.45%
CYP2D6 inhibition	-	0.9463	94.63%
CYP1A2 inhibition	-	0.6875	68.75%
CYP2C8 inhibition	-	0.6363	63.63%
CYP inhibitory promiscuity	-	0.8255	82.55%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6755	67.55%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.9093	90.93%
Skin irritation	-	0.5961	59.61%
Skin corrosion	-	0.9514	95.14%
Ames mutagenesis	-	0.6854	68.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6880	68.80%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6198	61.98%
skin sensitisation	-	0.8608	86.08%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8223	82.23%
Acute Oral Toxicity (c)	III	0.3973	39.73%
Estrogen receptor binding	+	0.5459	54.59%
Androgen receptor binding	+	0.7164	71.64%
Thyroid receptor binding	+	0.5856	58.56%
Glucocorticoid receptor binding	+	0.8193	81.93%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7351	73.51%
Honey bee toxicity	-	0.8737	87.37%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6435	64.35%
Fish aquatic toxicity	+	0.9882	98.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.51%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.20%	91.11%
CHEMBL230	P35354	Cyclooxygenase-2	95.57%	89.63%
CHEMBL2581	P07339	Cathepsin D	95.50%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.11%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.72%	99.17%
CHEMBL221	P23219	Cyclooxygenase-1	89.47%	90.17%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.72%	93.56%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	88.02%	95.17%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	87.88%	92.86%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.43%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	87.27%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	85.41%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.97%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.82%	99.23%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.95%	96.90%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.88%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.03%	94.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.49%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.69%	91.24%
CHEMBL4040	P28482	MAP kinase ERK2	80.97%	83.82%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.84%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.51%	97.25%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.36%	96.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.14%	95.89%

Plants that contains it

• Sequoia sempervirens

Cross-Links

• PubChem: 163053861
• LOTUS: LTS0257938
• wikiData: Q105382529