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

Details

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Internal ID beb0b90b-adf0-4096-a0f0-93854753e7af
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,11R,13R,14S,17R)-3-[(2S,4S,5S,6R)-5-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-11,14-dihydroxy-10,13-dimethyl-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) CC1C(C(C(C(O1)OC2COC(C(C2O)O)OC3C(OC(CC3O)OC4CCC5(C(C4)CCC6C5C(CC7(C6(CCC7C8=CC(=O)OC8)O)C)O)C)C)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2CO[C@H]([C@@H]([C@H]2O)O)O[C@@H]3[C@H](O[C@@H](C[C@@H]3O)O[C@H]4CC[C@]5([C@@H](C4)CC[C@@H]6[C@@H]5[C@@H](C[C@]7([C@@]6(CC[C@@H]7C8=CC(=O)OC8)O)C)O)C)C)O)O)O
InChI InChI=1S/C40H62O16/c1-17-30(44)32(46)34(48)37(53-17)55-26-16-51-36(33(47)31(26)45)56-35-18(2)52-28(13-24(35)41)54-21-7-9-38(3)20(12-21)5-6-23-29(38)25(42)14-39(4)22(8-10-40(23,39)49)19-11-27(43)50-15-19/h11,17-18,20-26,28-37,41-42,44-49H,5-10,12-16H2,1-4H3/t17-,18+,20+,21-,22+,23+,24-,25+,26+,28+,29+,30-,31-,32+,33+,34+,35+,36-,37-,38-,39+,40-/m0/s1
InChI Key PKHQKJZFVQEEGY-COYMSKIXSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C40H62O16
Molecular Weight 798.90 g/mol
Exact Mass 798.40378589 g/mol
Topological Polar Surface Area (TPSA) 244.00 Ų
XlogP -1.30
Atomic LogP (AlogP) -0.23
H-Bond Acceptor 16
H-Bond Donor 8
Rotatable Bonds 7

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,11R,13R,14S,17R)-3-[(2S,4S,5S,6R)-5-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-11,14-dihydroxy-10,13-dimethyl-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 + 0.8849 88.49%
Caco-2 - 0.9049 90.49%
Blood Brain Barrier - 0.9000 90.00%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.8225 82.25%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9230 92.30%
OATP1B3 inhibitior + 0.9510 95.10%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9750 97.50%
BSEP inhibitior + 0.8879 88.79%
P-glycoprotein inhibitior + 0.7243 72.43%
P-glycoprotein substrate + 0.8126 81.26%
CYP3A4 substrate + 0.7269 72.69%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9026 90.26%
CYP3A4 inhibition - 0.9502 95.02%
CYP2C9 inhibition - 0.9264 92.64%
CYP2C19 inhibition - 0.9255 92.55%
CYP2D6 inhibition - 0.9373 93.73%
CYP1A2 inhibition - 0.9291 92.91%
CYP2C8 inhibition - 0.5951 59.51%
CYP inhibitory promiscuity - 0.9462 94.62%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5513 55.13%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.9314 93.14%
Skin irritation - 0.5296 52.96%
Skin corrosion - 0.9382 93.82%
Ames mutagenesis - 0.5770 57.70%
Human Ether-a-go-go-Related Gene inhibition + 0.8559 85.59%
Micronuclear - 0.8400 84.00%
Hepatotoxicity - 0.7717 77.17%
skin sensitisation - 0.9072 90.72%
Respiratory toxicity + 0.8222 82.22%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.5875 58.75%
Nephrotoxicity - 0.8516 85.16%
Acute Oral Toxicity (c) I 0.8002 80.02%
Estrogen receptor binding + 0.8759 87.59%
Androgen receptor binding + 0.8090 80.90%
Thyroid receptor binding - 0.7116 71.16%
Glucocorticoid receptor binding + 0.6553 65.53%
Aromatase binding + 0.7616 76.16%
PPAR gamma + 0.7645 76.45%
Honey bee toxicity - 0.5863 58.63%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity + 0.6100 61.00%
Fish aquatic toxicity + 0.9689 96.89%

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 99.19% 91.11%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 98.03% 96.77%
CHEMBL1994 P08235 Mineralocorticoid receptor 96.60% 100.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.26% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.67% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.51% 97.09%
CHEMBL3038469 P24941 CDK2/Cyclin A 93.32% 91.38%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.80% 96.09%
CHEMBL241 Q14432 Phosphodiesterase 3A 92.16% 92.94%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.30% 89.00%
CHEMBL3714130 P46095 G-protein coupled receptor 6 90.98% 97.36%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 90.38% 85.14%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 89.62% 94.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.36% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.71% 95.89%
CHEMBL2581 P07339 Cathepsin D 85.99% 98.95%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 85.78% 97.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.66% 99.23%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.74% 90.71%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 80.89% 100.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 80.83% 82.69%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.69% 95.89%
CHEMBL1871 P10275 Androgen Receptor 80.41% 96.43%
CHEMBL4530 P00488 Coagulation factor XIII 80.26% 96.00%

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.
Ornithogalum nutans

Cross-Links

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PubChem 162951897
LOTUS LTS0030965
wikiData Q105210428