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[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2S,3R,8R,9R,10S,13R,14S,16R,17R)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-3,16-dihydroxy-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl]oxy]oxan-2-yl]methyl acetate

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 f9287892-f3e2-43e9-893f-f30d4e1ad575
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
IUPAC Name [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2S,3R,8R,9R,10S,13R,14S,16R,17R)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-3,16-dihydroxy-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl]oxy]oxan-2-yl]methyl acetate
SMILES (Canonical) CC(=O)OCC1C(C(C(C(O1)OC2CC3C(=CCC4C3(CCC5(C4(CC(C5C(C)(C(=O)CCC(C)(C)O)O)O)C)C)C)C(C2O)(C)C)OC(=O)C)OC(=O)C)OC(=O)C
SMILES (Isomeric) CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2C[C@@H]3C(=CC[C@@H]4[C@]3(CC[C@]5([C@]4(C[C@H]([C@@H]5[C@](C)(C(=O)CCC(C)(C)O)O)O)C)C)C)C([C@H]2O)(C)C)OC(=O)C)OC(=O)C)OC(=O)C
InChI InChI=1S/C44H68O15/c1-22(45)54-21-30-33(55-23(2)46)34(56-24(3)47)35(57-25(4)48)38(59-30)58-29-19-27-26(40(7,8)37(29)51)13-14-31-41(27,9)17-18-42(10)36(28(49)20-43(31,42)11)44(12,53)32(50)15-16-39(5,6)52/h13,27-31,33-38,49,51-53H,14-21H2,1-12H3/t27-,28-,29+,30-,31-,33-,34+,35-,36+,37+,38-,41+,42-,43+,44+/m1/s1
InChI Key UXHIMBDZUHTFOC-CMSKIVIQSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C44H68O15
Molecular Weight 837.00 g/mol
Exact Mass 836.45582146 g/mol
Topological Polar Surface Area (TPSA) 222.00 Ų
XlogP 3.80
Atomic LogP (AlogP) 3.87
H-Bond Acceptor 15
H-Bond Donor 4
Rotatable Bonds 12

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2S,3R,8R,9R,10S,13R,14S,16R,17R)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-3,16-dihydroxy-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl]oxy]oxan-2-yl]methyl acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9505 95.05%
Caco-2 - 0.8613 86.13%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.8646 86.46%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8111 81.11%
OATP1B3 inhibitior + 0.9000 90.00%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.5965 59.65%
BSEP inhibitior + 0.9531 95.31%
P-glycoprotein inhibitior + 0.7784 77.84%
P-glycoprotein substrate - 0.5097 50.97%
CYP3A4 substrate + 0.7328 73.28%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8886 88.86%
CYP3A4 inhibition - 0.8033 80.33%
CYP2C9 inhibition - 0.7897 78.97%
CYP2C19 inhibition - 0.9198 91.98%
CYP2D6 inhibition - 0.9400 94.00%
CYP1A2 inhibition - 0.8627 86.27%
CYP2C8 inhibition + 0.6979 69.79%
CYP inhibitory promiscuity - 0.8809 88.09%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6798 67.98%
Eye corrosion - 0.9913 99.13%
Eye irritation - 0.9049 90.49%
Skin irritation + 0.5790 57.90%
Skin corrosion - 0.9414 94.14%
Ames mutagenesis - 0.6700 67.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6460 64.60%
Micronuclear - 0.7400 74.00%
Hepatotoxicity - 0.5621 56.21%
skin sensitisation - 0.9098 90.98%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity - 0.7297 72.97%
Acute Oral Toxicity (c) III 0.5884 58.84%
Estrogen receptor binding + 0.7743 77.43%
Androgen receptor binding + 0.7414 74.14%
Thyroid receptor binding - 0.4913 49.13%
Glucocorticoid receptor binding + 0.7874 78.74%
Aromatase binding + 0.6699 66.99%
PPAR gamma + 0.7991 79.91%
Honey bee toxicity - 0.5964 59.64%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.9846 98.46%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.92% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.14% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.99% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.84% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.45% 97.09%
CHEMBL5255 O00206 Toll-like receptor 4 89.37% 92.50%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.78% 86.33%
CHEMBL226 P30542 Adenosine A1 receptor 88.15% 95.93%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 87.42% 95.17%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 86.92% 96.95%
CHEMBL3401 O75469 Pregnane X receptor 86.21% 94.73%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.50% 89.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 85.44% 96.77%
CHEMBL340 P08684 Cytochrome P450 3A4 84.85% 91.19%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.83% 100.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.46% 100.00%
CHEMBL2581 P07339 Cathepsin D 82.51% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.00% 95.89%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 81.35% 95.56%
CHEMBL5028 O14672 ADAM10 80.79% 97.50%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.63% 94.33%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.03% 91.07%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 162929214
LOTUS LTS0160272
wikiData Q105280790