3-[(3S,5R,8R,9S,10S,12S,13S,14S,17R)-3-[(2S,3R,4S,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-12,14-dihydroxy-10,13-dimethyl-11-oxo-2,3,4,5,6,7,8,9,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

Details

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Internal ID aebe8903-3bbd-4857-90b9-9875cc19c86b
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
IUPAC Name 3-[(3S,5R,8R,9S,10S,12S,13S,14S,17R)-3-[(2S,3R,4S,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-12,14-dihydroxy-10,13-dimethyl-11-oxo-2,3,4,5,6,7,8,9,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
SMILES (Canonical) CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3C(=O)C(C5(C4(CCC5C6=CC(=O)OC6)O)C)O)C)O)OC)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@@H]([C@H]([C@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3C(=O)[C@H]([C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)O)C)O)OC)O
InChI InChI=1S/C30H44O10/c1-14-22(32)25(37-4)24(34)27(39-14)40-17-7-9-28(2)16(12-17)5-6-19-21(28)23(33)26(35)29(3)18(8-10-30(19,29)36)15-11-20(31)38-13-15/h11,14,16-19,21-22,24-27,32,34-36H,5-10,12-13H2,1-4H3/t14-,16+,17-,18+,19+,21+,22-,24+,25-,26+,27+,28-,29-,30-/m0/s1
InChI Key TYVPUZUDLFQZOP-CRIZSVAQSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C30H44O10
Molecular Weight 564.70 g/mol
Exact Mass 564.29344760 g/mol
Topological Polar Surface Area (TPSA) 152.00 Ų
XlogP 0.10
Atomic LogP (AlogP) 1.26
H-Bond Acceptor 10
H-Bond Donor 4
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,8R,9S,10S,12S,13S,14S,17R)-3-[(2S,3R,4S,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-12,14-dihydroxy-10,13-dimethyl-11-oxo-2,3,4,5,6,7,8,9,12,15,16,17-dodecahydro-1H-cyclopenta[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 + 0.9507 95.07%
Caco-2 - 0.8284 82.84%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.7993 79.93%
OATP2B1 inhibitior - 0.7208 72.08%
OATP1B1 inhibitior + 0.9259 92.59%
OATP1B3 inhibitior + 0.9765 97.65%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.8614 86.14%
BSEP inhibitior + 0.6350 63.50%
P-glycoprotein inhibitior + 0.5902 59.02%
P-glycoprotein substrate + 0.7826 78.26%
CYP3A4 substrate + 0.6985 69.85%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9074 90.74%
CYP3A4 inhibition - 0.8667 86.67%
CYP2C9 inhibition - 0.9068 90.68%
CYP2C19 inhibition - 0.9471 94.71%
CYP2D6 inhibition - 0.9473 94.73%
CYP1A2 inhibition - 0.9330 93.30%
CYP2C8 inhibition - 0.7306 73.06%
CYP inhibitory promiscuity - 0.9265 92.65%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5140 51.40%
Eye corrosion - 0.9896 98.96%
Eye irritation - 0.9398 93.98%
Skin irritation - 0.5328 53.28%
Skin corrosion - 0.9349 93.49%
Ames mutagenesis - 0.5801 58.01%
Human Ether-a-go-go-Related Gene inhibition + 0.7079 70.79%
Micronuclear - 0.7400 74.00%
Hepatotoxicity - 0.7250 72.50%
skin sensitisation - 0.9124 91.24%
Respiratory toxicity + 0.8556 85.56%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity - 0.6977 69.77%
Acute Oral Toxicity (c) I 0.8350 83.50%
Estrogen receptor binding + 0.7578 75.78%
Androgen receptor binding + 0.7872 78.72%
Thyroid receptor binding - 0.6071 60.71%
Glucocorticoid receptor binding + 0.6887 68.87%
Aromatase binding + 0.6499 64.99%
PPAR gamma + 0.5735 57.35%
Honey bee toxicity - 0.6849 68.49%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.6100 61.00%
Fish aquatic toxicity + 0.9625 96.25%

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 98.61% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.04% 96.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 94.15% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.41% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.12% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.96% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.00% 95.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.36% 94.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.99% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.35% 89.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 86.09% 96.77%
CHEMBL241 Q14432 Phosphodiesterase 3A 85.87% 92.94%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.53% 97.25%
CHEMBL2581 P07339 Cathepsin D 84.87% 98.95%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 84.54% 85.14%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.09% 95.89%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.88% 97.14%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 81.71% 81.11%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 81.20% 100.00%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.07% 90.71%
CHEMBL1937 Q92769 Histone deacetylase 2 80.83% 94.75%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.66% 99.23%
CHEMBL3714130 P46095 G-protein coupled receptor 6 80.66% 97.36%

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 162911779
LOTUS LTS0255629
wikiData Q105267761