methyl (4S,4aR,6S,7R,7aR)-6-hydroxy-7-methyl-1-oxo-4,4a,5,6,7,7a-hexahydro-3H-cyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: c75ae40b-9566-4eab-af6c-4cc92ba7447e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: methyl (4S,4aR,6S,7R,7aR)-6-hydroxy-7-methyl-1-oxo-4,4a,5,6,7,7a-hexahydro-3H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1C(CC2C1C(=O)OCC2C(=O)OC)O
• SMILES (Isomeric): C[C@H]1[C@H](C[C@@H]2[C@H]1C(=O)OC[C@H]2C(=O)OC)O
• InChI: InChI=1S/C11H16O5/c1-5-8(12)3-6-7(10(13)15-2)4-16-11(14)9(5)6/h5-9,12H,3-4H2,1-2H3/t5-,6-,7+,8-,9-/m0/s1
• InChI Key: ZIJJPBFFTPOEDU-PQFOHKHZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₆O₅
• Molecular Weight: 228.24 g/mol
• Exact Mass: 228.09977361 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.03
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9626	96.26%
Caco-2	+	0.6738	67.38%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6103	61.03%
OATP2B1 inhibitior	-	0.8499	84.99%
OATP1B1 inhibitior	+	0.9250	92.50%
OATP1B3 inhibitior	+	0.9611	96.11%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9672	96.72%
P-glycoprotein inhibitior	-	0.9646	96.46%
P-glycoprotein substrate	-	0.7154	71.54%
CYP3A4 substrate	+	0.5292	52.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8363	83.63%
CYP3A4 inhibition	-	0.8403	84.03%
CYP2C9 inhibition	-	0.9524	95.24%
CYP2C19 inhibition	-	0.9544	95.44%
CYP2D6 inhibition	-	0.9464	94.64%
CYP1A2 inhibition	-	0.8224	82.24%
CYP2C8 inhibition	-	0.9651	96.51%
CYP inhibitory promiscuity	-	0.9836	98.36%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9313	93.13%
Carcinogenicity (trinary)	Non-required	0.7509	75.09%
Eye corrosion	-	0.9571	95.71%
Eye irritation	-	0.7930	79.30%
Skin irritation	-	0.7478	74.78%
Skin corrosion	-	0.9279	92.79%
Ames mutagenesis	-	0.5591	55.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.7249	72.49%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.9066	90.66%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.7737	77.37%
Acute Oral Toxicity (c)	III	0.4885	48.85%
Estrogen receptor binding	-	0.6005	60.05%
Androgen receptor binding	+	0.6718	67.18%
Thyroid receptor binding	-	0.7184	71.84%
Glucocorticoid receptor binding	-	0.5115	51.15%
Aromatase binding	-	0.7865	78.65%
PPAR gamma	-	0.8338	83.38%
Honey bee toxicity	-	0.7759	77.59%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.4384	43.84%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	93.99%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.97%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.71%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	88.89%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.18%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.17%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.90%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.60%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.85%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.72%	89.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.56%	95.71%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163022275
• LOTUS: LTS0276310
• wikiData: Q105376394