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3-[(3S,5R,8S,9R,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

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 e15c663a-59ba-4c9b-b969-9c051dee06ab
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
IUPAC Name 3-[(3S,5R,8S,9R,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
SMILES (Canonical) CC12CCC(CC1CCC3C2CCC4(C3(CCC4C5=CC(=O)OC5)O)C)OC6C(C(C(C(O6)CO)O)O)O
SMILES (Isomeric) C[C@]12CC[C@@H](C[C@H]1CC[C@H]3[C@H]2CC[C@]4([C@@]3(CC[C@@H]4C5=CC(=O)OC5)O)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
InChI InChI=1S/C29H44O9/c1-27-8-5-17(37-26-25(34)24(33)23(32)21(13-30)38-26)12-16(27)3-4-20-19(27)6-9-28(2)18(7-10-29(20,28)35)15-11-22(31)36-14-15/h11,16-21,23-26,30,32-35H,3-10,12-14H2,1-2H3/t16-,17+,18-,19-,20+,21-,23-,24+,25-,26-,27+,28-,29+/m1/s1
InChI Key CMHWMOGWFZWDMR-WFDZXWMQSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C29H44O9
Molecular Weight 536.70 g/mol
Exact Mass 536.29853298 g/mol
Topological Polar Surface Area (TPSA) 146.00 Ų
XlogP 1.60
Atomic LogP (AlogP) 1.43
H-Bond Acceptor 9
H-Bond Donor 5
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 3-[(3S,5R,8S,9R,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8248 82.48%
Caco-2 - 0.8582 85.82%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.8382 83.82%
OATP2B1 inhibitior - 0.5987 59.87%
OATP1B1 inhibitior + 0.9288 92.88%
OATP1B3 inhibitior + 0.9481 94.81%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.6431 64.31%
P-glycoprotein inhibitior - 0.5141 51.41%
P-glycoprotein substrate + 0.5803 58.03%
CYP3A4 substrate + 0.7023 70.23%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9010 90.10%
CYP3A4 inhibition - 0.9241 92.41%
CYP2C9 inhibition - 0.9242 92.42%
CYP2C19 inhibition - 0.9271 92.71%
CYP2D6 inhibition - 0.9231 92.31%
CYP1A2 inhibition - 0.9045 90.45%
CYP2C8 inhibition - 0.7599 75.99%
CYP inhibitory promiscuity - 0.9179 91.79%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6086 60.86%
Eye corrosion - 0.9907 99.07%
Eye irritation - 0.9430 94.30%
Skin irritation - 0.5648 56.48%
Skin corrosion - 0.9423 94.23%
Ames mutagenesis - 0.6770 67.70%
Human Ether-a-go-go-Related Gene inhibition + 0.8749 87.49%
Micronuclear - 0.8600 86.00%
Hepatotoxicity - 0.7500 75.00%
skin sensitisation - 0.9189 91.89%
Respiratory toxicity + 0.9000 90.00%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity - 0.7605 76.05%
Acute Oral Toxicity (c) I 0.8357 83.57%
Estrogen receptor binding + 0.7777 77.77%
Androgen receptor binding + 0.8361 83.61%
Thyroid receptor binding - 0.6170 61.70%
Glucocorticoid receptor binding + 0.6038 60.38%
Aromatase binding + 0.6855 68.55%
PPAR gamma - 0.5054 50.54%
Honey bee toxicity - 0.6916 69.16%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.9498 94.98%

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 98.58% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.26% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.93% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 95.81% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 95.59% 100.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.10% 97.25%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.70% 86.33%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 88.45% 96.77%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.98% 95.89%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 87.94% 96.21%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.67% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 86.98% 85.14%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.84% 94.00%
CHEMBL226 P30542 Adenosine A1 receptor 85.39% 95.93%
CHEMBL5255 O00206 Toll-like receptor 4 85.14% 92.50%
CHEMBL2581 P07339 Cathepsin D 84.99% 98.95%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 83.67% 82.69%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.74% 93.04%

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.
Digitalis lanata

Cross-Links

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PubChem 163189721
LOTUS LTS0027590
wikiData Q104964584