PlantaeDB Logo
Login Sign-up

(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-3-[(2R,4S,5R,6R)-4-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carboxylic acid

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 281955b1-6966-46ef-b602-b700de8a5d41
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
IUPAC Name (3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-3-[(2R,4S,5R,6R)-4-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carboxylic acid
SMILES (Canonical) CC1C(C(CC(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)C(=O)O)O)OC7C(C(C(C(O7)CO)O)O)O
SMILES (Isomeric) C[C@@H]1[C@@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@@]5([C@H](CC[C@@]5([C@@H]4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)C(=O)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
InChI InChI=1S/C35H52O15/c1-16-29(50-30-28(41)27(40)26(39)23(14-36)49-30)22(37)12-25(47-16)48-18-3-9-34(31(42)43)20-4-7-32(2)19(17-11-24(38)46-15-17)6-10-35(32,45)21(20)5-8-33(34,44)13-18/h11,16,18-23,25-30,36-37,39-41,44-45H,3-10,12-15H2,1-2H3,(H,42,43)/t16-,18+,19-,20+,21-,22+,23-,25+,26-,27+,28-,29+,30+,32-,33+,34-,35+/m1/s1
InChI Key RJPUPUKGXDXYFO-CDOIBZKASA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C35H52O15
Molecular Weight 712.80 g/mol
Exact Mass 712.33062095 g/mol
Topological Polar Surface Area (TPSA) 242.00 Ų
XlogP -1.20
Atomic LogP (AlogP) -0.51
H-Bond Acceptor 14
H-Bond Donor 8
Rotatable Bonds 7

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of (3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-3-[(2R,4S,5R,6R)-4-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carboxylic acid

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7963 79.63%
Caco-2 - 0.8827 88.27%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.8579 85.79%
OATP2B1 inhibitior - 0.8709 87.09%
OATP1B1 inhibitior + 0.9017 90.17%
OATP1B3 inhibitior + 0.9593 95.93%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior - 0.5457 54.57%
P-glycoprotein inhibitior + 0.6797 67.97%
P-glycoprotein substrate + 0.6840 68.40%
CYP3A4 substrate + 0.7133 71.33%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9006 90.06%
CYP3A4 inhibition - 0.8731 87.31%
CYP2C9 inhibition - 0.9132 91.32%
CYP2C19 inhibition - 0.9341 93.41%
CYP2D6 inhibition - 0.9343 93.43%
CYP1A2 inhibition - 0.9128 91.28%
CYP2C8 inhibition + 0.4646 46.46%
CYP inhibitory promiscuity - 0.9382 93.82%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5864 58.64%
Eye corrosion - 0.9901 99.01%
Eye irritation - 0.9220 92.20%
Skin irritation - 0.5515 55.15%
Skin corrosion - 0.9392 93.92%
Ames mutagenesis - 0.5640 56.40%
Human Ether-a-go-go-Related Gene inhibition + 0.7842 78.42%
Micronuclear - 0.7700 77.00%
Hepatotoxicity - 0.7102 71.02%
skin sensitisation - 0.9252 92.52%
Respiratory toxicity + 0.8556 85.56%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity - 0.8901 89.01%
Acute Oral Toxicity (c) I 0.8538 85.38%
Estrogen receptor binding + 0.8155 81.55%
Androgen receptor binding + 0.8016 80.16%
Thyroid receptor binding - 0.6378 63.78%
Glucocorticoid receptor binding + 0.6090 60.90%
Aromatase binding + 0.6855 68.55%
PPAR gamma + 0.6614 66.14%
Honey bee toxicity - 0.7129 71.29%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.6000 60.00%
Fish aquatic toxicity + 0.9644 96.44%

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 98.74% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.08% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 96.40% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 96.14% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.11% 94.45%
CHEMBL1994 P08235 Mineralocorticoid receptor 93.99% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.72% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.20% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.07% 97.25%
CHEMBL2581 P07339 Cathepsin D 84.99% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.83% 89.00%
CHEMBL5255 O00206 Toll-like receptor 4 84.73% 92.50%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 84.66% 81.11%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 83.39% 96.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.14% 99.23%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 83.11% 94.33%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 82.27% 96.77%
CHEMBL3714130 P46095 G-protein coupled receptor 6 81.97% 97.36%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 80.47% 96.21%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.23% 95.89%

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.
Erysimum cheiranthoides

Cross-Links

Top
PubChem 10919611
LOTUS LTS0031402
wikiData Q105237670