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[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (3S,5S,8R,9S,10S,13R,14S,17R)-3,5,14-trihydroxy-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-carboxylate

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 1d0ad66d-2248-4a7c-9096-d9cc49013b8f
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives
IUPAC Name [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (3S,5S,8R,9S,10S,13R,14S,17R)-3,5,14-trihydroxy-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-carboxylate
SMILES (Canonical) CC12CCC3C(C1(CCC2C4=CC(=O)OC4)O)CCC5(C3(CCC(C5)O)C(=O)OC6C(C(C(C(O6)CO)O)O)O)O
SMILES (Isomeric) C[C@]12CC[C@H]3[C@H]([C@]1(CC[C@@H]2C4=CC(=O)OC4)O)CC[C@]5([C@@]3(CC[C@@H](C5)O)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O
InChI InChI=1S/C29H42O12/c1-26-6-3-17-18(29(26,38)9-5-16(26)14-10-20(32)39-13-14)4-7-27(37)11-15(31)2-8-28(17,27)25(36)41-24-23(35)22(34)21(33)19(12-30)40-24/h10,15-19,21-24,30-31,33-35,37-38H,2-9,11-13H2,1H3/t15-,16+,17-,18+,19+,21+,22-,23+,24-,26+,27-,28+,29-/m0/s1
InChI Key YUTGBJOKGUMFPZ-GFNZSKBBSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C29H42O12
Molecular Weight 582.60 g/mol
Exact Mass 582.26762677 g/mol
Topological Polar Surface Area (TPSA) 203.00 Ų
XlogP -1.10
Atomic LogP (AlogP) -0.96
H-Bond Acceptor 12
H-Bond Donor 7
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (3S,5S,8R,9S,10S,13R,14S,17R)-3,5,14-trihydroxy-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-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7960 79.60%
Caco-2 - 0.8763 87.63%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.8567 85.67%
OATP2B1 inhibitior - 0.7276 72.76%
OATP1B1 inhibitior + 0.8926 89.26%
OATP1B3 inhibitior + 0.9607 96.07%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior - 0.6779 67.79%
P-glycoprotein inhibitior - 0.5561 55.61%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.7102 71.02%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8899 88.99%
CYP3A4 inhibition - 0.9209 92.09%
CYP2C9 inhibition - 0.9067 90.67%
CYP2C19 inhibition - 0.9158 91.58%
CYP2D6 inhibition - 0.9317 93.17%
CYP1A2 inhibition - 0.8984 89.84%
CYP2C8 inhibition + 0.4640 46.40%
CYP inhibitory promiscuity - 0.9407 94.07%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5659 56.59%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.9299 92.99%
Skin irritation - 0.5796 57.96%
Skin corrosion - 0.9385 93.85%
Ames mutagenesis - 0.6370 63.70%
Human Ether-a-go-go-Related Gene inhibition + 0.8102 81.02%
Micronuclear - 0.7800 78.00%
Hepatotoxicity - 0.7177 71.77%
skin sensitisation - 0.9206 92.06%
Respiratory toxicity + 0.8333 83.33%
Reproductive toxicity + 0.8222 82.22%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity - 0.8564 85.64%
Acute Oral Toxicity (c) I 0.7451 74.51%
Estrogen receptor binding + 0.8612 86.12%
Androgen receptor binding + 0.8042 80.42%
Thyroid receptor binding - 0.5976 59.76%
Glucocorticoid receptor binding + 0.5882 58.82%
Aromatase binding + 0.7133 71.33%
PPAR gamma + 0.5773 57.73%
Honey bee toxicity - 0.7259 72.59%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.6000 60.00%
Fish aquatic toxicity + 0.9579 95.79%

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 98.84% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.50% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 96.26% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.90% 94.45%
CHEMBL1994 P08235 Mineralocorticoid receptor 94.34% 100.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.43% 85.14%
CHEMBL2581 P07339 Cathepsin D 90.48% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.91% 86.33%
CHEMBL5255 O00206 Toll-like receptor 4 88.47% 92.50%
CHEMBL226 P30542 Adenosine A1 receptor 87.92% 95.93%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 87.16% 96.21%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.30% 95.89%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.15% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.14% 95.56%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 85.04% 93.04%
CHEMBL3922 P50579 Methionine aminopeptidase 2 84.21% 97.28%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 83.38% 81.11%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 83.22% 96.77%
CHEMBL4208 P20618 Proteasome component C5 82.21% 90.00%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 82.13% 94.33%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.99% 94.00%

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.
Antiaris toxicaria

Cross-Links

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PubChem 73352257
LOTUS LTS0253079
wikiData Q105364938