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

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 c42784ac-a374-4724-9784-fbdcd2301ca5
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,16S,17S)-5,14,16-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
SMILES (Canonical) CC12CCC3C(C1(CC(C2C4=CC(=O)OC4)O)O)CCC5(C3(CCC(C5)OC6C(C(C(C(O6)CO)O)O)O)C=O)O
SMILES (Isomeric) C[C@]12CC[C@H]3[C@H]([C@]1(C[C@@H]([C@H]2C4=CC(=O)OC4)O)O)CC[C@]5([C@@]3(CC[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C=O)O
InChI InChI=1S/C29H42O12/c1-26-5-3-16-17(29(26,38)10-18(32)21(26)14-8-20(33)39-12-14)4-7-28(37)9-15(2-6-27(16,28)13-31)40-25-24(36)23(35)22(34)19(11-30)41-25/h8,13,15-19,21-25,30,32,34-38H,2-7,9-12H2,1H3/t15-,16-,17+,18-,19+,21+,22+,23-,24+,25+,26+,27-,28-,29-/m0/s1
InChI Key DHKKVQBQUJXKMB-JLFYFGLKSA-N
Popularity 0 references 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 -2.10
Atomic LogP (AlogP) -1.31
H-Bond Acceptor 12
H-Bond Donor 7
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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

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 - 0.8947 89.47%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.8567 85.67%
OATP2B1 inhibitior - 0.7366 73.66%
OATP1B1 inhibitior + 0.8951 89.51%
OATP1B3 inhibitior + 0.9607 96.07%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior - 0.6120 61.20%
P-glycoprotein inhibitior - 0.4832 48.32%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.7104 71.04%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8962 89.62%
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 + 0.5084 50.84%
CYP inhibitory promiscuity - 0.9407 94.07%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5659 56.59%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.9355 93.55%
Skin irritation - 0.5796 57.96%
Skin corrosion - 0.9385 93.85%
Ames mutagenesis - 0.5793 57.93%
Human Ether-a-go-go-Related Gene inhibition + 0.8379 83.79%
Micronuclear - 0.7800 78.00%
Hepatotoxicity - 0.6267 62.67%
skin sensitisation - 0.9206 92.06%
Respiratory toxicity + 0.8111 81.11%
Reproductive toxicity + 0.8222 82.22%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity - 0.6871 68.71%
Acute Oral Toxicity (c) I 0.7451 74.51%
Estrogen receptor binding + 0.8303 83.03%
Androgen receptor binding + 0.8109 81.09%
Thyroid receptor binding - 0.5890 58.90%
Glucocorticoid receptor binding + 0.6141 61.41%
Aromatase binding + 0.6963 69.63%
PPAR gamma + 0.5659 56.59%
Honey bee toxicity - 0.7431 74.31%
Biodegradation - 0.6250 62.50%
Crustacea aquatic toxicity - 0.5500 55.00%
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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.22% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.51% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.86% 97.25%
CHEMBL1994 P08235 Mineralocorticoid receptor 95.27% 100.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.81% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.29% 97.09%
CHEMBL2581 P07339 Cathepsin D 92.20% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.25% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.70% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.92% 85.14%
CHEMBL226 P30542 Adenosine A1 receptor 88.93% 95.93%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.74% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.85% 89.00%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 82.82% 96.21%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 81.24% 96.00%
CHEMBL1871 P10275 Androgen Receptor 80.54% 96.43%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.26% 100.00%

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.
Strophanthus kombe

Cross-Links

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PubChem 162939228
LOTUS LTS0160945
wikiData Q104980305