(5S)-5-[(1R,2R,5R)-2-acetyl-5-methylcyclopentyl]-5-hydroxy-4-propan-2-ylfuran-2-one

Details

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Internal ID 052f8de0-9443-41b7-8860-1929da7f6989
Taxonomy Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
IUPAC Name (5S)-5-[(1R,2R,5R)-2-acetyl-5-methylcyclopentyl]-5-hydroxy-4-propan-2-ylfuran-2-one
SMILES (Canonical) CC1CCC(C1C2(C(=CC(=O)O2)C(C)C)O)C(=O)C
SMILES (Isomeric) C[C@@H]1CC[C@H]([C@@H]1[C@]2(C(=CC(=O)O2)C(C)C)O)C(=O)C
InChI InChI=1S/C15H22O4/c1-8(2)12-7-13(17)19-15(12,18)14-9(3)5-6-11(14)10(4)16/h7-9,11,14,18H,5-6H2,1-4H3/t9-,11+,14-,15-/m1/s1
InChI Key LNHHETCHVOGQEP-VNLRXTSXSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C15H22O4
Molecular Weight 266.33 g/mol
Exact Mass 266.15180918 g/mol
Topological Polar Surface Area (TPSA) 63.60 Ų
XlogP 1.60
Atomic LogP (AlogP) 2.07
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (5S)-5-[(1R,2R,5R)-2-acetyl-5-methylcyclopentyl]-5-hydroxy-4-propan-2-ylfuran-2-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9409 94.09%
Caco-2 + 0.6531 65.31%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability + 0.5714 57.14%
Subcellular localzation Mitochondria 0.7194 71.94%
OATP2B1 inhibitior - 0.8530 85.30%
OATP1B1 inhibitior + 0.9499 94.99%
OATP1B3 inhibitior + 0.9051 90.51%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior - 0.8569 85.69%
P-glycoprotein inhibitior - 0.8493 84.93%
P-glycoprotein substrate - 0.7397 73.97%
CYP3A4 substrate + 0.5877 58.77%
CYP2C9 substrate - 0.8028 80.28%
CYP2D6 substrate - 0.8913 89.13%
CYP3A4 inhibition - 0.8894 88.94%
CYP2C9 inhibition - 0.7214 72.14%
CYP2C19 inhibition - 0.7944 79.44%
CYP2D6 inhibition - 0.9275 92.75%
CYP1A2 inhibition - 0.5607 56.07%
CYP2C8 inhibition - 0.8634 86.34%
CYP inhibitory promiscuity - 0.8498 84.98%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9128 91.28%
Carcinogenicity (trinary) Non-required 0.5393 53.93%
Eye corrosion - 0.9611 96.11%
Eye irritation - 0.9231 92.31%
Skin irritation + 0.5420 54.20%
Skin corrosion - 0.8208 82.08%
Ames mutagenesis - 0.7870 78.70%
Human Ether-a-go-go-Related Gene inhibition - 0.6095 60.95%
Micronuclear - 0.8100 81.00%
Hepatotoxicity + 0.7668 76.68%
skin sensitisation - 0.7136 71.36%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity - 0.5889 58.89%
Mitochondrial toxicity + 0.5250 52.50%
Nephrotoxicity + 0.5946 59.46%
Acute Oral Toxicity (c) III 0.5582 55.82%
Estrogen receptor binding - 0.6199 61.99%
Androgen receptor binding + 0.7124 71.24%
Thyroid receptor binding - 0.5389 53.89%
Glucocorticoid receptor binding - 0.6076 60.76%
Aromatase binding - 0.8097 80.97%
PPAR gamma - 0.7712 77.12%
Honey bee toxicity - 0.8885 88.85%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.9735 97.35%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.03% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.84% 96.09%
CHEMBL2581 P07339 Cathepsin D 94.78% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.24% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.14% 85.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.15% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.10% 97.09%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 86.04% 96.77%
CHEMBL3359 P21462 Formyl peptide receptor 1 85.69% 93.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.90% 99.23%
CHEMBL340 P08684 Cytochrome P450 3A4 83.89% 91.19%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.00% 94.00%
CHEMBL4208 P20618 Proteasome component C5 81.62% 90.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.23% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.00% 86.33%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 80.96% 94.80%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 80.51% 97.21%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.32% 94.45%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Alpinia japonica

Cross-Links

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PubChem 13855702
LOTUS LTS0243219
wikiData Q105154339