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Gitaloxin

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 8d84af14-c1d9-4db1-a543-7308bb3619f6
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
IUPAC Name [(3S,5R,8R,9S,10S,13R,14S,16S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] formate
SMILES (Canonical) CC1C(C(CC(O1)OC2C(OC(CC2O)OC3C(OC(CC3O)OC4CCC5(C(C4)CCC6C5CCC7(C6(CC(C7C8=CC(=O)OC8)OC=O)O)C)C)C)C)O)O
SMILES (Isomeric) C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2O)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]5CC[C@]7([C@@]6(C[C@@H]([C@@H]7C8=CC(=O)OC8)OC=O)O)C)C)C)C)O)O
InChI InChI=1S/C42H64O15/c1-20-37(48)28(44)14-34(52-20)56-39-22(3)54-35(16-30(39)46)57-38-21(2)53-33(15-29(38)45)55-25-8-10-40(4)24(13-25)6-7-27-26(40)9-11-41(5)36(23-12-32(47)50-18-23)31(51-19-43)17-42(27,41)49/h12,19-22,24-31,33-39,44-46,48-49H,6-11,13-18H2,1-5H3/t20-,21-,22-,24-,25+,26+,27-,28+,29+,30+,31+,33+,34+,35+,36+,37-,38-,39-,40+,41-,42+/m1/s1
InChI Key GZZJHPZDXZCDDA-MBJUQXSJSA-N
Popularity 11 references in papers

Physical and Chemical Properties

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Molecular Formula C42H64O15
Molecular Weight 808.90 g/mol
Exact Mass 808.42452133 g/mol
Topological Polar Surface Area (TPSA) 209.00 Ų
XlogP 2.10
Atomic LogP (AlogP) 2.40
H-Bond Acceptor 15
H-Bond Donor 5
Rotatable Bonds 9

Synonyms

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Cristaloxine
Gitoxin 16-formate
16-Formyl-gitoxin
Gitaloxinum
Gitaloxina
Gitaloxine
Gitaloxin [INN]
Gitaloxigenin-tridigitoxosid
16-formylgitoxin
3261-53-8
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Gitaloxin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9551 95.51%
Caco-2 - 0.9054 90.54%
Blood Brain Barrier - 0.7500 75.00%
Human oral bioavailability + 0.6714 67.14%
Subcellular localzation Mitochondria 0.8783 87.83%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9243 92.43%
OATP1B3 inhibitior + 0.9509 95.09%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.9281 92.81%
P-glycoprotein inhibitior + 0.7392 73.92%
P-glycoprotein substrate + 0.8821 88.21%
CYP3A4 substrate + 0.7010 70.10%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9028 90.28%
CYP3A4 inhibition - 0.8598 85.98%
CYP2C9 inhibition - 0.9008 90.08%
CYP2C19 inhibition - 0.9395 93.95%
CYP2D6 inhibition - 0.9508 95.08%
CYP1A2 inhibition - 0.9063 90.63%
CYP2C8 inhibition - 0.7483 74.83%
CYP inhibitory promiscuity - 0.9585 95.85%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.4953 49.53%
Eye corrosion - 0.9904 99.04%
Eye irritation - 0.9362 93.62%
Skin irritation + 0.5744 57.44%
Skin corrosion - 0.9325 93.25%
Ames mutagenesis + 0.5230 52.30%
Human Ether-a-go-go-Related Gene inhibition + 0.8350 83.50%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.7342 73.42%
skin sensitisation - 0.9129 91.29%
Respiratory toxicity + 0.8889 88.89%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity - 0.8217 82.17%
Acute Oral Toxicity (c) I 0.8720 87.20%
Estrogen receptor binding + 0.8780 87.80%
Androgen receptor binding + 0.8253 82.53%
Thyroid receptor binding - 0.7188 71.88%
Glucocorticoid receptor binding + 0.7171 71.71%
Aromatase binding + 0.7487 74.87%
PPAR gamma + 0.7815 78.15%
Honey bee toxicity - 0.6263 62.63%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity + 0.6500 65.00%
Fish aquatic toxicity + 0.9856 98.56%

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
CHEMBL1994 P08235 Mineralocorticoid receptor 97.30% 100.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.21% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.32% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.84% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.41% 86.33%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 91.68% 82.69%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.65% 94.45%
CHEMBL5608 Q16288 NT-3 growth factor receptor 90.49% 95.89%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.59% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.68% 89.00%
CHEMBL1871 P10275 Androgen Receptor 86.62% 96.43%
CHEMBL4208 P20618 Proteasome component C5 86.38% 90.00%
CHEMBL241 Q14432 Phosphodiesterase 3A 85.81% 92.94%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.65% 99.23%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 83.03% 96.77%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 82.02% 90.71%
CHEMBL253 P34972 Cannabinoid CB2 receptor 81.80% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.89% 85.14%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 80.04% 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.
Digitalis ciliata
Digitalis lanata
Digitalis purpurea

Cross-Links

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PubChem 10440404
NPASS NPC149410
LOTUS LTS0228045
wikiData Q27139239