Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:55:43 UTC
Update Date2021-09-14 15:17:02 UTC
HMDB IDHMDB0060731
Secondary Accession Numbers
  • HMDB60731
Metabolite Identification
Common NameDigoxigenin
DescriptionDigoxigenin belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. Digoxigenin is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866097
SynonymsNot Available
Chemical FormulaC23H34O5
Average Molecular Weight390.5131
Monoisotopic Molecular Weight390.240624198
IUPAC Name4-[(1S,2S,5S,7R,11S,14R,15S,16R)-5,11,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one
Traditional Name4-[(1S,2S,5S,7R,11S,14R,15S,16R)-5,11,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-5H-furan-2-one
CAS Registry NumberNot Available
SMILES
C[C@@]12[C@H](CC[C@]1(O)C1CC[C@@H]3C[C@@H](O)CC[C@]3(C)[C@H]1C[C@H]2O)C1=CC(=O)OC1
InChI Identifier
InChI=1S/C23H34O5/c1-21-7-5-15(24)10-14(21)3-4-17-18(21)11-19(25)22(2)16(6-8-23(17,22)27)13-9-20(26)28-12-13/h9,14-19,24-25,27H,3-8,10-12H2,1-2H3/t14-,15+,16-,17?,18+,19-,21+,22+,23+/m1/s1
InChI KeySHIBSTMRCDJXLN-UHJLBCFUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentCardenolides and derivatives
Alternative Parents
Substituents
  • Cardanolide-skeleton
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 12-hydroxysteroid
  • 14-hydroxysteroid
  • Hydroxysteroid
  • 2-furanone
  • Cyclic alcohol
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Lactone
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.063 g/LALOGPS
logP1.6ALOGPS
logP1.84ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.15ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity105.16 m³·mol⁻¹ChemAxon
Polarizability42.9 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+190.68731661259
DarkChem[M-H]-184.97831661259
DeepCCS[M-2H]-225.96830932474
DeepCCS[M+Na]+201.16230932474
AllCCS[M+H]+197.932859911
AllCCS[M+H-H2O]+195.532859911
AllCCS[M+NH4]+200.132859911
AllCCS[M+Na]+200.732859911
AllCCS[M-H]-198.232859911
AllCCS[M+Na-2H]-198.932859911
AllCCS[M+HCOO]-199.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DigoxigeninC[C@@]12[C@H](CC[C@]1(O)C1CC[C@@H]3C[C@@H](O)CC[C@]3(C)[C@H]1C[C@H]2O)C1=CC(=O)OC13569.3Standard polar33892256
DigoxigeninC[C@@]12[C@H](CC[C@]1(O)C1CC[C@@H]3C[C@@H](O)CC[C@]3(C)[C@H]1C[C@H]2O)C1=CC(=O)OC13393.0Standard non polar33892256
DigoxigeninC[C@@]12[C@H](CC[C@]1(O)C1CC[C@@H]3C[C@@H](O)CC[C@]3(C)[C@H]1C[C@H]2O)C1=CC(=O)OC14006.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Digoxigenin,1TMS,isomer #1C[C@]12CC[C@H](O)C[C@H]1CCC1[C@@H]2C[C@@H](O)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O[Si](C)(C)C3509.6Semi standard non polar33892256
Digoxigenin,1TMS,isomer #2C[C@]12CC[C@H](O[Si](C)(C)C)C[C@H]1CCC1[C@@H]2C[C@@H](O)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O3508.5Semi standard non polar33892256
Digoxigenin,1TMS,isomer #3C[C@]12CC[C@H](O)C[C@H]1CCC1[C@@H]2C[C@@H](O[Si](C)(C)C)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O3498.9Semi standard non polar33892256
Digoxigenin,2TMS,isomer #1C[C@]12CC[C@H](O[Si](C)(C)C)C[C@H]1CCC1[C@@H]2C[C@@H](O)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O[Si](C)(C)C3501.1Semi standard non polar33892256
Digoxigenin,2TMS,isomer #2C[C@]12CC[C@H](O)C[C@H]1CCC1[C@@H]2C[C@@H](O[Si](C)(C)C)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O[Si](C)(C)C3513.4Semi standard non polar33892256
Digoxigenin,2TMS,isomer #3C[C@]12CC[C@H](O[Si](C)(C)C)C[C@H]1CCC1[C@@H]2C[C@@H](O[Si](C)(C)C)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O3493.3Semi standard non polar33892256
Digoxigenin,3TMS,isomer #1C[C@]12CC[C@H](O[Si](C)(C)C)C[C@H]1CCC1[C@@H]2C[C@@H](O[Si](C)(C)C)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O[Si](C)(C)C3463.2Semi standard non polar33892256
Digoxigenin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@]12CC[C@H](C3=CC(=O)OC3)[C@@]1(C)[C@H](O)C[C@H]1C2CC[C@@H]2C[C@@H](O)CC[C@]12C3749.9Semi standard non polar33892256
Digoxigenin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1CC[C@]2(C)[C@H]3C[C@@H](O)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]4(O)C3CC[C@@H]2C13750.3Semi standard non polar33892256
Digoxigenin,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2C(CC[C@@H]3C[C@@H](O)CC[C@]23C)[C@@]2(O)CC[C@H](C3=CC(=O)OC3)[C@@]12C3742.1Semi standard non polar33892256
Digoxigenin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2C(CC[C@@H]3C[C@@H](O)CC[C@]23C)[C@@]2(O[Si](C)(C)C(C)(C)C)CC[C@H](C3=CC(=O)OC3)[C@@]12C3979.8Semi standard non polar33892256
Digoxigenin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1CC[C@]2(C)[C@H]3C[C@@H](O)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]4(O[Si](C)(C)C(C)(C)C)C3CC[C@@H]2C13947.1Semi standard non polar33892256
Digoxigenin,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1CC[C@]2(C)[C@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]4(O)C3CC[C@@H]2C13942.4Semi standard non polar33892256
Digoxigenin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@]2(C)[C@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]4(O[Si](C)(C)C(C)(C)C)C3CC[C@@H]2C14106.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Digoxigenin GC-MS (Non-derivatized) - 70eV, Positivesplash10-024i-0429000000-f7c82abf5771f14d5f5d2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Digoxigenin GC-MS (3 TMS) - 70eV, Positivesplash10-0006-1021290000-70d92b89773e3736426a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Digoxigenin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Digoxigenin 10V, Positive-QTOFsplash10-05fr-0009000000-b59c5cf6c115137b57782017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Digoxigenin 20V, Positive-QTOFsplash10-0c00-0019000000-5677b46505a603760dc62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Digoxigenin 40V, Positive-QTOFsplash10-0gb9-6629000000-33f01d364dd3b3a25f9b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Digoxigenin 10V, Negative-QTOFsplash10-000i-0009000000-73a0d171eca6ffd63abf2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Digoxigenin 20V, Negative-QTOFsplash10-00ds-0009000000-67ceadb6751d356cb8ee2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Digoxigenin 40V, Negative-QTOFsplash10-0036-1109000000-2c7d971ebc142e8899152017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Digoxigenin 10V, Positive-QTOFsplash10-006x-0019000000-f2227b806735a9067f492021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Digoxigenin 20V, Positive-QTOFsplash10-0abl-0149000000-7eaecb9aed880f68f6812021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Digoxigenin 40V, Positive-QTOFsplash10-002b-4932000000-04503200006f5dabc96c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Digoxigenin 10V, Negative-QTOFsplash10-000i-0009000000-5ce939f19fc9d3c1ef5e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Digoxigenin 20V, Negative-QTOFsplash10-000b-0009000000-37c6cc9767e62d07b6cd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Digoxigenin 40V, Negative-QTOFsplash10-0079-3229000000-8dbf20437a81f2a971fe2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDigoxigenin
METLIN IDNot Available
PubChem Compound131769933
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.