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[(2R,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl] (1S,3R,6S,7S,12S,14R,15R,16R)-14-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-7,12,16-trimethyl-15-[(2R)-6-methylhept-5-en-2-yl]-6-[(2R,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylate

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 188f2ea8-ce6e-496d-b5a7-d9386d258f5e
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
IUPAC Name [(2R,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl] (1S,3R,6S,7S,12S,14R,15R,16R)-14-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-7,12,16-trimethyl-15-[(2R)-6-methylhept-5-en-2-yl]-6-[(2R,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylate
SMILES (Canonical) CC1C(C(C(C(O1)OC2CCC34CC35CCC6(C(C(CC6(C5CCC4C2(C)C(=O)OC7C(C(C(C(O7)C)O)O)O)C)OC8C(C(C(O8)CO)O)O)C(C)CCC=C(C)C)C)O)O)O
SMILES (Isomeric) CC1[C@@H]([C@@H](C([C@@H](O1)O[C@H]2CC[C@]34C[C@]35CC[C@@]6([C@H]([C@@H](C[C@]6(C5CCC4[C@]2(C)C(=O)O[C@H]7C([C@H]([C@H](C(O7)C)O)O)O)C)O[C@H]8C([C@H]([C@H](O8)CO)O)O)[C@H](C)CCC=C(C)C)C)O)O)O
InChI InChI=1S/C47H76O16/c1-21(2)10-9-11-22(3)30-25(60-41-36(54)33(51)26(19-48)61-41)18-44(7)27-12-13-28-45(8,42(57)63-40-38(56)35(53)32(50)24(5)59-40)29(62-39-37(55)34(52)31(49)23(4)58-39)14-15-46(28)20-47(27,46)17-16-43(30,44)6/h10,22-41,48-56H,9,11-20H2,1-8H3/t22-,23?,24?,25-,26-,27?,28?,29+,30+,31+,32+,33+,34+,35+,36?,37?,38?,39+,40+,41-,43-,44+,45+,46-,47+/m1/s1
InChI Key ITKGAUOSWSGWTN-FYVCSJOKSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C47H76O16
Molecular Weight 897.10 g/mol
Exact Mass 896.51333633 g/mol
Topological Polar Surface Area (TPSA) 255.00 Ų
XlogP 3.80
Atomic LogP (AlogP) 1.81
H-Bond Acceptor 16
H-Bond Donor 9
Rotatable Bonds 11

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2R,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl] (1S,3R,6S,7S,12S,14R,15R,16R)-14-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-7,12,16-trimethyl-15-[(2R)-6-methylhept-5-en-2-yl]-6-[(2R,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8503 85.03%
Caco-2 - 0.8801 88.01%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.8207 82.07%
OATP2B1 inhibitior - 0.8768 87.68%
OATP1B1 inhibitior + 0.8255 82.55%
OATP1B3 inhibitior + 0.8680 86.80%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.6250 62.50%
BSEP inhibitior + 0.6546 65.46%
P-glycoprotein inhibitior + 0.7723 77.23%
P-glycoprotein substrate - 0.5302 53.02%
CYP3A4 substrate + 0.7151 71.51%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8541 85.41%
CYP3A4 inhibition - 0.9049 90.49%
CYP2C9 inhibition - 0.6670 66.70%
CYP2C19 inhibition - 0.8574 85.74%
CYP2D6 inhibition - 0.9238 92.38%
CYP1A2 inhibition - 0.8202 82.02%
CYP2C8 inhibition + 0.5874 58.74%
CYP inhibitory promiscuity - 0.8347 83.47%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6305 63.05%
Eye corrosion - 0.9892 98.92%
Eye irritation - 0.9070 90.70%
Skin irritation - 0.5806 58.06%
Skin corrosion - 0.9401 94.01%
Ames mutagenesis - 0.7178 71.78%
Human Ether-a-go-go-Related Gene inhibition + 0.7485 74.85%
Micronuclear - 0.7900 79.00%
Hepatotoxicity - 0.8115 81.15%
skin sensitisation - 0.8815 88.15%
Respiratory toxicity - 0.5111 51.11%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity - 0.5125 51.25%
Nephrotoxicity - 0.8762 87.62%
Acute Oral Toxicity (c) III 0.4677 46.77%
Estrogen receptor binding + 0.7697 76.97%
Androgen receptor binding + 0.7510 75.10%
Thyroid receptor binding - 0.5335 53.35%
Glucocorticoid receptor binding + 0.7000 70.00%
Aromatase binding + 0.6328 63.28%
PPAR gamma + 0.7626 76.26%
Honey bee toxicity - 0.6536 65.36%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6455 64.55%
Fish aquatic toxicity + 0.9767 97.67%

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 99.24% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.39% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.66% 96.09%
CHEMBL2581 P07339 Cathepsin D 94.29% 98.95%
CHEMBL3837 P07711 Cathepsin L 92.47% 96.61%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.43% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.33% 97.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 91.15% 96.61%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.95% 89.00%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 89.90% 91.24%
CHEMBL340 P08684 Cytochrome P450 3A4 88.41% 91.19%
CHEMBL2413 P32246 C-C chemokine receptor type 1 88.00% 89.50%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 87.84% 98.75%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 87.66% 95.58%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.50% 100.00%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 87.27% 95.83%
CHEMBL4683 Q12884 Fibroblast activation protein alpha 87.16% 93.07%
CHEMBL284 P27487 Dipeptidyl peptidase IV 86.83% 95.69%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 86.25% 96.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.93% 95.89%
CHEMBL241 Q14432 Phosphodiesterase 3A 85.86% 92.94%
CHEMBL237 P41145 Kappa opioid receptor 85.74% 98.10%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 85.63% 92.88%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 85.37% 95.50%
CHEMBL3359 P21462 Formyl peptide receptor 1 84.90% 93.56%
CHEMBL4394 Q9NYA1 Sphingosine kinase 1 84.71% 96.03%
CHEMBL2534 O15530 3-phosphoinositide dependent protein kinase-1 84.63% 95.36%
CHEMBL1937 Q92769 Histone deacetylase 2 84.50% 94.75%
CHEMBL4005 P42336 PI3-kinase p110-alpha subunit 84.49% 97.47%
CHEMBL5888 Q99558 Mitogen-activated protein kinase kinase kinase 14 84.24% 100.00%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.72% 100.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.56% 92.62%
CHEMBL1951 P21397 Monoamine oxidase A 83.17% 91.49%
CHEMBL1293316 Q9HBX9 Relaxin receptor 1 82.76% 82.50%
CHEMBL4105786 P41182 B-cell lymphoma 6 protein 82.61% 92.86%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.38% 95.50%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 82.38% 100.00%
CHEMBL2007625 O75874 Isocitrate dehydrogenase [NADP] cytoplasmic 82.34% 99.00%
CHEMBL2842 P42345 Serine/threonine-protein kinase mTOR 82.21% 92.78%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 82.14% 97.50%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 81.84% 96.47%
CHEMBL2955 O95136 Sphingosine 1-phosphate receptor Edg-5 80.99% 92.86%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.83% 86.33%

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.
Amphilophium paniculatum

Cross-Links

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PubChem 162817417
LOTUS LTS0211120
wikiData Q105120106