PlantaeDB Logo
Login Sign-up

[(6R)-6-[(2S,3S,8R,9R,10R,13R,14S,16R,17R)-3,16-dihydroxy-4,4,9,13,14-pentamethyl-11-oxo-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxoheptan-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

Top
Internal ID 99933824-0a70-4c51-a0b4-157ce668a106
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
IUPAC Name [(6R)-6-[(2S,3S,8R,9R,10R,13R,14S,16R,17R)-3,16-dihydroxy-4,4,9,13,14-pentamethyl-11-oxo-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxoheptan-2-yl] acetate
SMILES (Canonical) CC(=O)OC(C)(C)CCC(=O)C(C)(C1C(CC2(C1(CC(=O)C3(C2CC=C4C3CC(C(C4(C)C)O)OC5C(C(C(C(O5)CO)O)O)O)C)C)C)O)O
SMILES (Isomeric) CC(=O)OC(C)(C)CCC(=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@H](C4(C)C)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C)C)O)O
InChI InChI=1S/C38H60O13/c1-18(40)51-33(2,3)13-12-25(42)38(9,48)30-21(41)15-35(6)24-11-10-19-20(37(24,8)26(43)16-36(30,35)7)14-22(31(47)34(19,4)5)49-32-29(46)28(45)27(44)23(17-39)50-32/h10,20-24,27-32,39,41,44-48H,11-17H2,1-9H3/t20-,21-,22+,23-,24-,27-,28+,29-,30+,31-,32-,35+,36-,37+,38+/m1/s1
InChI Key BCTZZCQBLBDVRU-CXGBXGRJSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

Top
Molecular Formula C38H60O13
Molecular Weight 724.90 g/mol
Exact Mass 724.40339196 g/mol
Topological Polar Surface Area (TPSA) 221.00 Ų
XlogP 1.00
Atomic LogP (AlogP) 1.34
H-Bond Acceptor 13
H-Bond Donor 7
Rotatable Bonds 9

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of [(6R)-6-[(2S,3S,8R,9R,10R,13R,14S,16R,17R)-3,16-dihydroxy-4,4,9,13,14-pentamethyl-11-oxo-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxoheptan-2-yl] acetate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8868 88.68%
Caco-2 - 0.8663 86.63%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.8714 87.14%
Subcellular localzation Mitochondria 0.8704 87.04%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8251 82.51%
OATP1B3 inhibitior + 0.8029 80.29%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.5600 56.00%
BSEP inhibitior + 0.6562 65.62%
P-glycoprotein inhibitior + 0.7583 75.83%
P-glycoprotein substrate + 0.5142 51.42%
CYP3A4 substrate + 0.7240 72.40%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8893 88.93%
CYP3A4 inhibition - 0.7708 77.08%
CYP2C9 inhibition - 0.7891 78.91%
CYP2C19 inhibition - 0.9175 91.75%
CYP2D6 inhibition - 0.9430 94.30%
CYP1A2 inhibition - 0.8441 84.41%
CYP2C8 inhibition + 0.6574 65.74%
CYP inhibitory promiscuity - 0.9293 92.93%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6868 68.68%
Eye corrosion - 0.9907 99.07%
Eye irritation - 0.9119 91.19%
Skin irritation + 0.5434 54.34%
Skin corrosion - 0.9407 94.07%
Ames mutagenesis - 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6903 69.03%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.6302 63.02%
skin sensitisation - 0.9183 91.83%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity - 0.6053 60.53%
Acute Oral Toxicity (c) III 0.6943 69.43%
Estrogen receptor binding + 0.6716 67.16%
Androgen receptor binding + 0.7487 74.87%
Thyroid receptor binding - 0.5376 53.76%
Glucocorticoid receptor binding + 0.7763 77.63%
Aromatase binding + 0.7044 70.44%
PPAR gamma + 0.7186 71.86%
Honey bee toxicity - 0.6288 62.88%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.9750 97.50%

Targets

Top

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 99.48% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.26% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.47% 96.09%
CHEMBL2581 P07339 Cathepsin D 96.28% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 95.36% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.52% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.89% 97.25%
CHEMBL2996 Q05655 Protein kinase C delta 88.18% 97.79%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.98% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.70% 95.56%
CHEMBL4208 P20618 Proteasome component C5 84.65% 90.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.53% 89.00%
CHEMBL5255 O00206 Toll-like receptor 4 83.87% 92.50%
CHEMBL241 Q14432 Phosphodiesterase 3A 82.91% 92.94%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.67% 100.00%
CHEMBL3401 O75469 Pregnane X receptor 82.35% 94.73%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.10% 94.00%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 82.06% 97.33%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 81.30% 96.95%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 80.80% 85.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.70% 99.23%

Plants that contains it

Top
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.
Hemsleya graciliflora

Cross-Links

Top
PubChem 162924140
LOTUS LTS0029523
wikiData Q104923641