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[(E,6R)-6-hydroxy-6-[(2S,8S,9R,10R,13R,14S,16R,17R)-16-hydroxy-9-(hydroxymethyl)-4,4,13,14-tetramethyl-3,11-dioxo-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxohept-3-en-2-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 b478e361-f438-474c-9455-793a1d805695
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
IUPAC Name [(E,6R)-6-hydroxy-6-[(2S,8S,9R,10R,13R,14S,16R,17R)-16-hydroxy-9-(hydroxymethyl)-4,4,13,14-tetramethyl-3,11-dioxo-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxohept-3-en-2-yl] acetate
SMILES (Canonical) CC(=O)OC(C)(C)C=CC(=O)C(C)(C1C(CC2(C1(CC(=O)C3(C2CC=C4C3CC(C(=O)C4(C)C)OC5C(C(C(C(O5)CO)O)O)O)CO)C)C)O)O
SMILES (Isomeric) CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2([C@@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C[C@@H](C(=O)C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)CO)C)C)O)O
InChI InChI=1S/C38H56O14/c1-18(41)52-33(2,3)12-11-25(43)37(8,49)30-21(42)14-35(6)24-10-9-19-20(38(24,17-40)26(44)15-36(30,35)7)13-22(31(48)34(19,4)5)50-32-29(47)28(46)27(45)23(16-39)51-32/h9,11-12,20-24,27-30,32,39-40,42,45-47,49H,10,13-17H2,1-8H3/b12-11+/t20-,21-,22+,23-,24+,27-,28+,29-,30+,32-,35+,36-,37+,38+/m1/s1
InChI Key BTKXYYIQKCDSPF-XNCXWTMSSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C38H56O14
Molecular Weight 736.80 g/mol
Exact Mass 736.36700646 g/mol
Topological Polar Surface Area (TPSA) 238.00 Ų
XlogP 0.40
Atomic LogP (AlogP) 0.30
H-Bond Acceptor 14
H-Bond Donor 7
Rotatable Bonds 9

Synonyms

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AKOS040763066
Cucurbitacin A 2-O-??-D-glucopyranoside
1135141-76-2

2D Structure

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2D Structure of [(E,6R)-6-hydroxy-6-[(2S,8S,9R,10R,13R,14S,16R,17R)-16-hydroxy-9-(hydroxymethyl)-4,4,13,14-tetramethyl-3,11-dioxo-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxohept-3-en-2-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 + 0.8568 85.68%
Caco-2 - 0.8639 86.39%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.8203 82.03%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8176 81.76%
OATP1B3 inhibitior + 0.8596 85.96%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.7797 77.97%
P-glycoprotein inhibitior + 0.7557 75.57%
P-glycoprotein substrate + 0.5459 54.59%
CYP3A4 substrate + 0.7273 72.73%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8984 89.84%
CYP3A4 inhibition - 0.8613 86.13%
CYP2C9 inhibition - 0.8593 85.93%
CYP2C19 inhibition - 0.8990 89.90%
CYP2D6 inhibition - 0.9430 94.30%
CYP1A2 inhibition - 0.8732 87.32%
CYP2C8 inhibition + 0.6749 67.49%
CYP inhibitory promiscuity - 0.9363 93.63%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6662 66.62%
Eye corrosion - 0.9896 98.96%
Eye irritation - 0.9125 91.25%
Skin irritation - 0.6002 60.02%
Skin corrosion - 0.9434 94.34%
Ames mutagenesis - 0.6200 62.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3920 39.20%
Micronuclear - 0.7100 71.00%
Hepatotoxicity - 0.5900 59.00%
skin sensitisation - 0.8881 88.81%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity + 0.6013 60.13%
Acute Oral Toxicity (c) III 0.6322 63.22%
Estrogen receptor binding + 0.7515 75.15%
Androgen receptor binding + 0.7633 76.33%
Thyroid receptor binding + 0.5166 51.66%
Glucocorticoid receptor binding + 0.8037 80.37%
Aromatase binding + 0.6712 67.12%
PPAR gamma + 0.7531 75.31%
Honey bee toxicity - 0.6401 64.01%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.9783 97.83%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 99.06% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.95% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.43% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.57% 96.09%
CHEMBL2581 P07339 Cathepsin D 94.51% 98.95%
CHEMBL1293294 P51151 Ras-related protein Rab-9A 94.44% 87.67%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 94.40% 96.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.86% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.89% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.78% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.77% 95.56%
CHEMBL3401 O75469 Pregnane X receptor 87.69% 94.73%
CHEMBL2996 Q05655 Protein kinase C delta 86.77% 97.79%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.91% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.82% 89.00%
CHEMBL2095226 P05556 Integrin alpha-5/beta-1 84.92% 96.39%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.91% 100.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.44% 91.07%
CHEMBL299 P17252 Protein kinase C alpha 80.30% 98.03%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 80.03% 91.24%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 80.00% 96.21%

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.
Cucumis melo

Cross-Links

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PubChem 44139484
NPASS NPC76526
LOTUS LTS0253901
wikiData Q104945689