Record Information |
---|
Version | 1.0 |
---|
Created at | 2022-09-09 15:32:04 UTC |
---|
Updated at | 2022-09-09 15:32:05 UTC |
---|
NP-MRD ID | NP0286789 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | β-acetyldigoxin |
---|
Description | Beta-Acetyldigoxin, also known as corotal or novodigal, belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. β-acetyldigoxin is found in Digitalis lanata. It was first documented in 2005 (PMID: 15731979). Based on a literature review a significant number of articles have been published on beta-Acetyldigoxin (PMID: 32035664) (PMID: 36113990) (PMID: 36113989) (PMID: 36113988) (PMID: 36113987) (PMID: 36113986). |
---|
Structure | C[C@H]1O[C@H](C[C@H](O)[C@@H]1O[C@H]1C[C@H](O)[C@H](O[C@H]2C[C@H](O)[C@H](OC(C)=O)[C@@H](C)O2)[C@@H](C)O1)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2C[C@@H](O)[C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)C1 InChI=1S/C43H66O15/c1-20-38(55-23(4)44)30(45)17-36(53-20)57-40-22(3)54-37(18-32(40)47)58-39-21(2)52-35(16-31(39)46)56-26-9-11-41(5)25(14-26)7-8-28-29(41)15-33(48)42(6)27(10-12-43(28,42)50)24-13-34(49)51-19-24/h13,20-22,25-33,35-40,45-48,50H,7-12,14-19H2,1-6H3/t20-,21-,22-,25-,26+,27-,28-,29+,30+,31+,32+,33-,35+,36+,37+,38-,39-,40-,41+,42+,43+/m1/s1 |
---|
Synonyms | Value | Source |
---|
Acetyldigoxin beta isomer | Kegg | Corotal | Kegg | Acetyldigoxin b isomer | Generator | Acetyldigoxin β isomer | Generator | b-Acetyldigoxin | Generator | Β-acetyldigoxin | Generator | Novodigal | MeSH | CT, Digox von | MeSH | Glycotop | MeSH | Acetyldigoxins | MeSH | Digotab | MeSH | Digox von CT | MeSH | Von CT, digox | MeSH | Desglucolanatosides C | MeSH | Digostada | MeSH | alpha Acetyldigoxin | MeSH | alpha-Acetyldigoxin | MeSH | Didier, digoxin | MeSH | Digoxin didier | MeSH | Gladixol N | MeSH | Kardiamed | MeSH | Longdigox | MeSH | Stillacor | MeSH | beta Acetyldigoxin | MeSH |
|
---|
Chemical Formula | C43H66O15 |
---|
Average Mass | 822.9860 Da |
---|
Monoisotopic Mass | 822.44017 Da |
---|
IUPAC Name | (2R,3S,4S,6S)-6-{[(2R,3S,4S,6S)-6-{[(2R,3S,4S,6R)-6-{[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2-methyloxan-3-yl acetate |
---|
Traditional Name | (2R,3S,4S,6S)-6-{[(2R,3S,4S,6S)-6-{[(2R,3S,4S,6R)-6-{[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-2,15-dimethyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2-methyloxan-3-yl acetate |
---|
CAS Registry Number | Not Available |
---|
SMILES | C[C@H]1O[C@H](C[C@H](O)[C@@H]1O[C@H]1C[C@H](O)[C@H](O[C@H]2C[C@H](O)[C@H](OC(C)=O)[C@@H](C)O2)[C@@H](C)O1)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2C[C@@H](O)[C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)C1 |
---|
InChI Identifier | InChI=1S/C43H66O15/c1-20-38(55-23(4)44)30(45)17-36(53-20)57-40-22(3)54-37(18-32(40)47)58-39-21(2)52-35(16-31(39)46)56-26-9-11-41(5)25(14-26)7-8-28-29(41)15-33(48)42(6)27(10-12-43(28,42)50)24-13-34(49)51-19-24/h13,20-22,25-33,35-40,45-48,50H,7-12,14-19H2,1-6H3/t20-,21-,22-,25-,26+,27-,28-,29+,30+,31+,32+,33-,35+,36+,37+,38-,39-,40-,41+,42+,43+/m1/s1 |
---|
InChI Key | NREAGDHHMSOWKZ-DXJNJSHLSA-N |
---|
Experimental Spectra |
---|
|
| Not Available | Predicted Spectra |
---|
|
| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Steroids and steroid derivatives |
---|
Sub Class | Steroid lactones |
---|
Direct Parent | Cardenolide glycosides and derivatives |
---|
Alternative Parents | |
---|
Substituents | - Cardanolide-glycoside
- Steroidal glycoside
- Oligosaccharide
- 12-hydroxysteroid
- 14-hydroxysteroid
- Hydroxysteroid
- Glycosyl compound
- O-glycosyl compound
- 2-furanone
- Dicarboxylic acid or derivatives
- Oxane
- Cyclic alcohol
- Dihydrofuran
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tertiary alcohol
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Acetal
- Carboxylic acid derivative
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- Aliphatic heteropolycyclic compound
|
---|
Molecular Framework | Aliphatic heteropolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
General References | - Ravi BG, Guardian MGE, Dickman R, Wang ZQ: Profiling and structural analysis of cardenolides in two species of Digitalis using liquid chromatography coupled with high-resolution mass spectrometry. J Chromatogr A. 2020 May 10;1618:460903. doi: 10.1016/j.chroma.2020.460903. Epub 2020 Jan 22. [PubMed:32035664 ]
- Concha-Miranda M, Tang W, Hartmann K, Brecht M: Large-scale mapping of vocalization-related activity in the functionally diverse nuclei in rat posterior brainstem. J Neurosci. 2022 Sep 16. pii: JNEUROSCI.0813-22.2022. doi: 10.1523/JNEUROSCI.0813-22.2022. [PubMed:36113990 ]
- Kausto J, Gluschkoff K, Turunen J, Selinheimo S, Peutere L, Vaananen A: Psychotherapy and change in mental health-related work disability: a prospective Finnish population-level register-based study with a quasi-experimental design. J Epidemiol Community Health. 2022 Sep 16. pii: jech-2022-218941. doi: 10.1136/jech-2022-218941. [PubMed:36113989 ]
- Meulemans L, Baert Desurmont S, Waill MC, Castelain G, Killian A, Hauchard J, Frebourg T, Coulet F, Martins A, Muleris M, Gaildrat P: Comprehensive RNA and protein functional assessments contribute to the clinical interpretation of MSH2 variants causing in-frame splicing alterations. J Med Genet. 2022 Sep 16. pii: jmg-2022-108576. doi: 10.1136/jmg-2022-108576. [PubMed:36113988 ]
- Otsuji S, Nishio Y, Tsujita M, Rio M, Huber C, Anton-Plagaro C, Mizuno S, Kawano Y, Miyatake S, Simon M, van Binsbergen E, van Jaarsveld RH, Matsumoto N, Cormier-Daire V, J Cullen P, Saitoh S, Kato K: Clinical diversity and molecular mechanism of VPS35L-associated Ritscher-Schinzel syndrome. J Med Genet. 2022 Sep 16. pii: jmg-2022-108602. doi: 10.1136/jmg-2022-108602. [PubMed:36113987 ]
- Crul M, Breukels O: Safe handling of cytostatic drugs: recommendations from independent science. Eur J Hosp Pharm. 2022 Sep 16. pii: ejhpharm-2022-003469. doi: 10.1136/ejhpharm-2022-003469. [PubMed:36113986 ]
- Kroshus E, Chrisman SPD, Glang A, Hunt T, Hays R, Lowry S, Peterson A, Garrett K, Ramshaw D, Hafferty K, Kinney E, Manzueta M, Steiner MK, Bollinger BJ, Chiampas G, Rivara FP: Concussion education for youth athletes using Pre-Game Safety Huddles: a cluster-randomised controlled trial. Inj Prev. 2022 Sep 16. pii: ip-2022-044665. doi: 10.1136/ip-2022-044665. [PubMed:36113984 ]
- Hwang J, Kelz R: Impact of medical education on patient safety: finding the signal through the noise. BMJ Qual Saf. 2022 Sep 16. pii: bmjqs-2022-015054. doi: 10.1136/bmjqs-2022-015054. [PubMed:36113985 ]
- Munoz J, Palacios-Corella M, Gomez IJ, Zajickova L, Pumera M: Synthetic Nanoarchitectonics of Functional Organic-Inorganic 2D Germanane Heterostructures via Click Chemistry. Adv Mater. 2022 Sep 16:e2206382. doi: 10.1002/adma.202206382. [PubMed:36113982 ]
- Ravi BG, Guardian MGE, Dickman R, Wang ZQ: High-resolution tandem mass spectrometry dataset reveals fragmentation patterns of cardiac glycosides in leaves of the foxglove plants. Data Brief. 2020 Mar 20;30:105464. doi: 10.1016/j.dib.2020.105464. eCollection 2020 Jun. [PubMed:32300626 ]
- Sukoyan GV, Gongadze NV: Mechanism of cardioprotective effect of adenocine and non-glycoside cardiotonic drugs during experimental chronic cardiac insufficiency. Bull Exp Biol Med. 2011 Mar;150(5):610-3. doi: 10.1007/s10517-011-1203-5. [PubMed:22235397 ]
- Hauck C, Potter T, Bartz M, Wittwer T, Wahlers T, Mehlhorn U, Scheiner-Bobis G, McDonough AA, Bloch W, Schwinger RH, Muller-Ehmsen J: Isoform specificity of cardiac glycosides binding to human Na+,K+-ATPase alpha1beta1, alpha2beta1 and alpha3beta1. Eur J Pharmacol. 2009 Nov 10;622(1-3):7-14. doi: 10.1016/j.ejphar.2009.08.039. Epub 2009 Sep 12. [PubMed:19751721 ]
- Sukoyan GV, Antelava NA: Rational drug correction of systemic inflammatory response syndrome in severe experimental heart failure. Bull Exp Biol Med. 2009 Apr;147(4):411-4. doi: 10.1007/s10517-009-0528-9. [PubMed:19704936 ]
- Potter T, Hauck C, Pocas ES, Diedrichs H, Adam C, Reuter H, Wittwer T, Wahlers T, da Silva AJ, Costa PR, Noel F, Muller-Ehmsen J: Inhibition of the alpha1beta1 isoform of the Na, K-ATPase by 8-methoxycoumestrol without positive inotropic effect in human myocardium--novel aspects of cardiac glycoside pharmacology. J Cardiovasc Pharmacol. 2009 Jul;54(1):10-5. doi: 10.1097/FJC.0b013e3181a95ab2. [PubMed:19487957 ]
- Anderer G, Hellmeyer L, Tekesin I, Schmidt S: [Combination therapy for fetal supraventricular tachycardia with flecainide and digoxin]. Z Geburtshilfe Neonatol. 2005 Feb;209(1):34-7. doi: 10.1055/s-2005-837798. [PubMed:15731979 ]
- LOTUS database [Link]
|
---|