[(5R,6R,7S,8R,9R,10R,13S,17R)-6-hydroxy-17-[(2R)-2-hydroxy-5-oxo-2H-furan-4-yl]-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-yl] acetate

Details

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Internal ID 2f026be9-d06c-4fe4-8a10-8947265a09d3
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
IUPAC Name [(5R,6R,7S,8R,9R,10R,13S,17R)-6-hydroxy-17-[(2R)-2-hydroxy-5-oxo-2H-furan-4-yl]-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-yl] acetate
SMILES (Canonical) CC(=O)OC1C(C2C(C(=O)C=CC2(C3C1(C4=CCC(C4(CC3)C)C5=CC(OC5=O)O)C)C)(C)C)O
SMILES (Isomeric) CC(=O)O[C@@H]1[C@@H]([C@@H]2[C@](C=CC(=O)C2(C)C)([C@@H]3[C@@]1(C4=CC[C@H]([C@@]4(CC3)C)C5=C[C@@H](OC5=O)O)C)C)O
InChI InChI=1S/C28H36O7/c1-14(29)34-23-21(32)22-25(2,3)19(30)10-12-27(22,5)18-9-11-26(4)16(7-8-17(26)28(18,23)6)15-13-20(31)35-24(15)33/h8,10,12-13,16,18,20-23,31-32H,7,9,11H2,1-6H3/t16-,18+,20+,21+,22-,23+,26-,27+,28-/m0/s1
InChI Key SCRLXEQGNJOVBG-VPSQXFEBSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C28H36O7
Molecular Weight 484.60 g/mol
Exact Mass 484.24610348 g/mol
Topological Polar Surface Area (TPSA) 110.00 Ų
XlogP 3.40
Atomic LogP (AlogP) 3.25
H-Bond Acceptor 7
H-Bond Donor 2
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(5R,6R,7S,8R,9R,10R,13S,17R)-6-hydroxy-17-[(2R)-2-hydroxy-5-oxo-2H-furan-4-yl]-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9916 99.16%
Caco-2 - 0.7045 70.45%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.7578 75.78%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8315 83.15%
OATP1B3 inhibitior - 0.2473 24.73%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior - 0.5547 55.47%
P-glycoprotein inhibitior + 0.6792 67.92%
P-glycoprotein substrate - 0.6106 61.06%
CYP3A4 substrate + 0.7073 70.73%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8968 89.68%
CYP3A4 inhibition - 0.6559 65.59%
CYP2C9 inhibition - 0.6492 64.92%
CYP2C19 inhibition - 0.8556 85.56%
CYP2D6 inhibition - 0.9331 93.31%
CYP1A2 inhibition - 0.6017 60.17%
CYP2C8 inhibition + 0.4890 48.90%
CYP inhibitory promiscuity - 0.7589 75.89%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4226 42.26%
Eye corrosion - 0.9883 98.83%
Eye irritation - 0.9396 93.96%
Skin irritation - 0.5227 52.27%
Skin corrosion - 0.9276 92.76%
Ames mutagenesis - 0.6800 68.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4595 45.95%
Micronuclear - 0.6900 69.00%
Hepatotoxicity - 0.5169 51.69%
skin sensitisation - 0.7926 79.26%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.6169 61.69%
Acute Oral Toxicity (c) I 0.5339 53.39%
Estrogen receptor binding + 0.7812 78.12%
Androgen receptor binding + 0.6818 68.18%
Thyroid receptor binding + 0.5938 59.38%
Glucocorticoid receptor binding + 0.7877 78.77%
Aromatase binding + 0.6259 62.59%
PPAR gamma + 0.6466 64.66%
Honey bee toxicity - 0.6875 68.75%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5450 54.50%
Fish aquatic toxicity + 1.0000 100.00%

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 98.38% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.03% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.00% 96.09%
CHEMBL2581 P07339 Cathepsin D 93.41% 98.95%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 89.40% 82.69%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.55% 100.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 88.03% 96.77%
CHEMBL340 P08684 Cytochrome P450 3A4 86.00% 91.19%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.86% 91.07%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.50% 99.23%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.49% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.96% 95.89%
CHEMBL5028 O14672 ADAM10 83.79% 97.50%
CHEMBL3922 P50579 Methionine aminopeptidase 2 83.67% 97.28%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.60% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.30% 86.33%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 83.15% 81.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.01% 95.56%

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.
Azadirachta indica

Cross-Links

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PubChem 162905858
LOTUS LTS0253765
wikiData Q105250366