[(2S,3S,5S)-5-[(2S)-3,3-dimethyloxiran-2-yl]-3-[(5R,9R,10R,13S,14S,17S)-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]oxolan-2-yl] acetate

Details

Top
Internal ID 90368fe0-8d3a-4df7-8913-b2f798f3ba93
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name [(2S,3S,5S)-5-[(2S)-3,3-dimethyloxiran-2-yl]-3-[(5R,9R,10R,13S,14S,17S)-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]oxolan-2-yl] acetate
SMILES (Canonical) CC(=O)OC1C(CC(O1)C2C(O2)(C)C)C3CCC4(C3(CCC5C4=CCC6C5(CCC(=O)C6(C)C)C)C)C
SMILES (Isomeric) CC(=O)O[C@H]1[C@@H](C[C@H](O1)[C@H]2C(O2)(C)C)[C@@H]3CC[C@]4([C@]3(CC[C@H]5C4=CC[C@@H]6[C@@]5(CCC(=O)C6(C)C)C)C)C
InChI InChI=1S/C32H48O5/c1-18(33)35-27-19(17-23(36-27)26-29(4,5)37-26)20-11-15-32(8)22-9-10-24-28(2,3)25(34)13-14-30(24,6)21(22)12-16-31(20,32)7/h9,19-21,23-24,26-27H,10-17H2,1-8H3/t19-,20-,21-,23-,24-,26-,27+,30+,31-,32+/m0/s1
InChI Key YIEYBMFKRXRFGE-DSDIBFMKSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

Top
Molecular Formula C32H48O5
Molecular Weight 512.70 g/mol
Exact Mass 512.35017463 g/mol
Topological Polar Surface Area (TPSA) 65.10 Ų
XlogP 6.30
Atomic LogP (AlogP) 6.63
H-Bond Acceptor 5
H-Bond Donor 0
Rotatable Bonds 3

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of [(2S,3S,5S)-5-[(2S)-3,3-dimethyloxiran-2-yl]-3-[(5R,9R,10R,13S,14S,17S)-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]oxolan-2-yl] acetate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9934 99.34%
Caco-2 - 0.6028 60.28%
Blood Brain Barrier + 0.8500 85.00%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.8110 81.10%
OATP2B1 inhibitior - 0.8626 86.26%
OATP1B1 inhibitior + 0.8259 82.59%
OATP1B3 inhibitior + 0.8041 80.41%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.8968 89.68%
P-glycoprotein inhibitior + 0.7777 77.77%
P-glycoprotein substrate - 0.6857 68.57%
CYP3A4 substrate + 0.7294 72.94%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8636 86.36%
CYP3A4 inhibition - 0.5425 54.25%
CYP2C9 inhibition - 0.7603 76.03%
CYP2C19 inhibition - 0.8218 82.18%
CYP2D6 inhibition - 0.9418 94.18%
CYP1A2 inhibition - 0.7550 75.50%
CYP2C8 inhibition + 0.7414 74.14%
CYP inhibitory promiscuity - 0.8079 80.79%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.4503 45.03%
Eye corrosion - 0.9867 98.67%
Eye irritation - 0.9317 93.17%
Skin irritation - 0.5885 58.85%
Skin corrosion - 0.8996 89.96%
Ames mutagenesis - 0.7300 73.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3703 37.03%
Micronuclear - 0.5000 50.00%
Hepatotoxicity - 0.5750 57.50%
skin sensitisation - 0.7976 79.76%
Respiratory toxicity + 0.8667 86.67%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity + 0.6591 65.91%
Acute Oral Toxicity (c) III 0.4210 42.10%
Estrogen receptor binding + 0.7358 73.58%
Androgen receptor binding + 0.7505 75.05%
Thyroid receptor binding + 0.6336 63.36%
Glucocorticoid receptor binding + 0.8138 81.38%
Aromatase binding + 0.7458 74.58%
PPAR gamma + 0.6877 68.77%
Honey bee toxicity - 0.7260 72.60%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.5100 51.00%
Fish aquatic toxicity + 0.9969 99.69%

Targets

Top

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 97.40% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.98% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.32% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 90.16% 100.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 87.76% 82.69%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.46% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.12% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.33% 99.23%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.99% 94.00%
CHEMBL340 P08684 Cytochrome P450 3A4 84.44% 91.19%
CHEMBL5255 O00206 Toll-like receptor 4 82.21% 92.50%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.03% 97.25%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.28% 92.62%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.14% 86.33%

Plants that contains it

Top
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.
Melia azedarach

Cross-Links

Top
PubChem 163052063
LOTUS LTS0087614
wikiData Q105348795