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[(2R,3S,4S,5S,6S)-3-acetyloxy-2-[[(2S,3S,8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,3-dihydroxy-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxy-6-methyloxan-4-yl] 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 732dca22-3c6e-4496-8033-669d61b02ce6
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
IUPAC Name [(2R,3S,4S,5S,6S)-3-acetyloxy-2-[[(2S,3S,8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,3-dihydroxy-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxy-6-methyloxan-4-yl] acetate
SMILES (Canonical) CC1C(C(C(C(O1)OC2CC3(C4CC=C5C(C4(C(=O)CC3(C2C(C)(C(=O)C=CC(C)(C)O)O)C)C)CC(C(C5(C)C)O)O)C)OC(=O)C)OC(=O)C)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@@H]([C@@H]([C@@H](O1)O[C@@H]2C[C@]3([C@@H]4CC=C5[C@H]([C@@]4(C(=O)C[C@@]3([C@H]2[C@](C)(C(=O)/C=C/C(C)(C)O)O)C)C)C[C@@H]([C@H](C5(C)C)O)O)C)OC(=O)C)OC(=O)C)O
InChI InChI=1S/C40H60O13/c1-19-29(46)30(51-20(2)41)31(52-21(3)42)34(50-19)53-25-17-37(8)26-13-12-22-23(16-24(43)33(47)36(22,6)7)39(26,10)28(45)18-38(37,9)32(25)40(11,49)27(44)14-15-35(4,5)48/h12,14-15,19,23-26,29-34,43,46-49H,13,16-18H2,1-11H3/b15-14+/t19-,23+,24-,25+,26-,29-,30-,31-,32-,33+,34-,37-,38+,39-,40-/m0/s1
InChI Key HBHXQUZCTLQSPY-ALNQIMNISA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C40H60O13
Molecular Weight 748.90 g/mol
Exact Mass 748.40339196 g/mol
Topological Polar Surface Area (TPSA) 206.00 Ų
XlogP 1.40
Atomic LogP (AlogP) 2.71
H-Bond Acceptor 13
H-Bond Donor 5
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2R,3S,4S,5S,6S)-3-acetyloxy-2-[[(2S,3S,8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,3-dihydroxy-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxy-6-methyloxan-4-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 + 0.9727 97.27%
Caco-2 - 0.8520 85.20%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.7900 79.00%
OATP2B1 inhibitior - 0.8583 85.83%
OATP1B1 inhibitior + 0.8209 82.09%
OATP1B3 inhibitior + 0.8603 86.03%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.9329 93.29%
P-glycoprotein inhibitior + 0.7748 77.48%
P-glycoprotein substrate + 0.5779 57.79%
CYP3A4 substrate + 0.7273 72.73%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8998 89.98%
CYP3A4 inhibition - 0.6803 68.03%
CYP2C9 inhibition - 0.8509 85.09%
CYP2C19 inhibition - 0.8530 85.30%
CYP2D6 inhibition - 0.9461 94.61%
CYP1A2 inhibition - 0.8058 80.58%
CYP2C8 inhibition + 0.6466 64.66%
CYP inhibitory promiscuity - 0.9549 95.49%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5831 58.31%
Eye corrosion - 0.9906 99.06%
Eye irritation - 0.9105 91.05%
Skin irritation + 0.5152 51.52%
Skin corrosion - 0.9302 93.02%
Ames mutagenesis - 0.6500 65.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4313 43.13%
Micronuclear - 0.6000 60.00%
Hepatotoxicity - 0.5017 50.17%
skin sensitisation - 0.8054 80.54%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8375 83.75%
Nephrotoxicity - 0.5757 57.57%
Acute Oral Toxicity (c) I 0.6041 60.41%
Estrogen receptor binding + 0.7397 73.97%
Androgen receptor binding + 0.7391 73.91%
Thyroid receptor binding + 0.5390 53.90%
Glucocorticoid receptor binding + 0.7873 78.73%
Aromatase binding + 0.6842 68.42%
PPAR gamma + 0.7379 73.79%
Honey bee toxicity - 0.6249 62.49%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.5800 58.00%
Fish aquatic toxicity + 0.9930 99.30%

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 99.18% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.25% 86.33%
CHEMBL2581 P07339 Cathepsin D 94.23% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.39% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.18% 96.09%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 90.08% 91.07%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.03% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.75% 89.00%
CHEMBL340 P08684 Cytochrome P450 3A4 89.05% 91.19%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.61% 85.14%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 86.97% 96.77%
CHEMBL1293294 P51151 Ras-related protein Rab-9A 86.88% 87.67%
CHEMBL3401 O75469 Pregnane X receptor 86.64% 94.73%
CHEMBL4208 P20618 Proteasome component C5 86.17% 90.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.46% 100.00%
CHEMBL4829 O00763 Acetyl-CoA carboxylase 2 83.72% 98.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.43% 94.00%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 83.13% 83.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.17% 99.23%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.75% 97.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 80.26% 97.25%

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 163193053
LOTUS LTS0010085
wikiData Q105025306