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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:46:17 UTC
Update Date2022-03-07 02:53:09 UTC
HMDB IDHMDB0031896
Secondary Accession Numbers
  • HMDB31896
Metabolite Identification
Common NameErinacine D
DescriptionErinacine D belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review a significant number of articles have been published on Erinacine D.
Structure
Data?1563862187
SynonymsNot Available
Chemical FormulaC27H42O7
Average Molecular Weight478.6182
Monoisotopic Molecular Weight478.293053698
IUPAC Name9-ethoxy-3a,5a-dimethyl-1-(propan-2-yl)-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2H,3H,3aH,4H,5H,5aH,6H,9H,10H,10aH-cyclohepta[e]indene-8-carbaldehyde
Traditional Name9-ethoxy-1-isopropyl-3a,5a-dimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2H,3H,4H,5H,6H,9H,10H,10aH-cyclohepta[e]indene-8-carbaldehyde
CAS Registry Number157397-40-5
SMILES
CCOC1CC2C3=C(CCC3(C)CCC2(C)C(OC2OCC(O)C(O)C2O)C=C1C=O)C(C)C
InChI Identifier
InChI=1S/C27H42O7/c1-6-32-20-12-18-22-17(15(2)3)7-8-26(22,4)9-10-27(18,5)21(11-16(20)13-28)34-25-24(31)23(30)19(29)14-33-25/h11,13,15,18-21,23-25,29-31H,6-10,12,14H2,1-5H3
InChI KeyZQHNREXELVXBCG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Diterpenoid
  • Glycosyl compound
  • O-glycosyl compound
  • Monosaccharide
  • Oxane
  • Secondary alcohol
  • Acetal
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point121 - 123 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.078 g/LALOGPS
logP2.5ALOGPS
logP2.3ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)12.25ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity128.85 m³·mol⁻¹ChemAxon
Polarizability53.13 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+210.43231661259
DarkChem[M-H]-203.2731661259
DeepCCS[M+H]+213.18530932474
DeepCCS[M-H]-210.82730932474
DeepCCS[M-2H]-244.23730932474
DeepCCS[M+Na]+219.91430932474
AllCCS[M+H]+216.732859911
AllCCS[M+H-H2O]+215.032859911
AllCCS[M+NH4]+218.332859911
AllCCS[M+Na]+218.732859911
AllCCS[M-H]-208.332859911
AllCCS[M+Na-2H]-210.032859911
AllCCS[M+HCOO]-212.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Erinacine DCCOC1CC2C3=C(CCC3(C)CCC2(C)C(OC2OCC(O)C(O)C2O)C=C1C=O)C(C)C3489.0Standard polar33892256
Erinacine DCCOC1CC2C3=C(CCC3(C)CCC2(C)C(OC2OCC(O)C(O)C2O)C=C1C=O)C(C)C3336.0Standard non polar33892256
Erinacine DCCOC1CC2C3=C(CCC3(C)CCC2(C)C(OC2OCC(O)C(O)C2O)C=C1C=O)C(C)C3489.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Erinacine D,1TMS,isomer #1CCOC1CC2C3=C(C(C)C)CCC3(C)CCC2(C)C(OC2OCC(O[Si](C)(C)C)C(O)C2O)C=C1C=O3725.5Semi standard non polar33892256
Erinacine D,1TMS,isomer #2CCOC1CC2C3=C(C(C)C)CCC3(C)CCC2(C)C(OC2OCC(O)C(O[Si](C)(C)C)C2O)C=C1C=O3695.0Semi standard non polar33892256
Erinacine D,1TMS,isomer #3CCOC1CC2C3=C(C(C)C)CCC3(C)CCC2(C)C(OC2OCC(O)C(O)C2O[Si](C)(C)C)C=C1C=O3676.8Semi standard non polar33892256
Erinacine D,2TMS,isomer #1CCOC1CC2C3=C(C(C)C)CCC3(C)CCC2(C)C(OC2OCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)C=C1C=O3684.9Semi standard non polar33892256
Erinacine D,2TMS,isomer #2CCOC1CC2C3=C(C(C)C)CCC3(C)CCC2(C)C(OC2OCC(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)C=C1C=O3653.1Semi standard non polar33892256
Erinacine D,2TMS,isomer #3CCOC1CC2C3=C(C(C)C)CCC3(C)CCC2(C)C(OC2OCC(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)C=C1C=O3660.0Semi standard non polar33892256
Erinacine D,3TMS,isomer #1CCOC1CC2C3=C(C(C)C)CCC3(C)CCC2(C)C(OC2OCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)C=C1C=O3657.6Semi standard non polar33892256
Erinacine D,1TBDMS,isomer #1CCOC1CC2C3=C(C(C)C)CCC3(C)CCC2(C)C(OC2OCC(O[Si](C)(C)C(C)(C)C)C(O)C2O)C=C1C=O3944.7Semi standard non polar33892256
Erinacine D,1TBDMS,isomer #2CCOC1CC2C3=C(C(C)C)CCC3(C)CCC2(C)C(OC2OCC(O)C(O[Si](C)(C)C(C)(C)C)C2O)C=C1C=O3918.0Semi standard non polar33892256
Erinacine D,1TBDMS,isomer #3CCOC1CC2C3=C(C(C)C)CCC3(C)CCC2(C)C(OC2OCC(O)C(O)C2O[Si](C)(C)C(C)(C)C)C=C1C=O3902.7Semi standard non polar33892256
Erinacine D,2TBDMS,isomer #1CCOC1CC2C3=C(C(C)C)CCC3(C)CCC2(C)C(OC2OCC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)C=C1C=O4107.2Semi standard non polar33892256
Erinacine D,2TBDMS,isomer #2CCOC1CC2C3=C(C(C)C)CCC3(C)CCC2(C)C(OC2OCC(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)C=C1C=O4092.4Semi standard non polar33892256
Erinacine D,2TBDMS,isomer #3CCOC1CC2C3=C(C(C)C)CCC3(C)CCC2(C)C(OC2OCC(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C=C1C=O4103.4Semi standard non polar33892256
Erinacine D,3TBDMS,isomer #1CCOC1CC2C3=C(C(C)C)CCC3(C)CCC2(C)C(OC2OCC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C=C1C=O4309.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Erinacine D GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gi-3311900000-f78706cd6424a399b7cd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erinacine D GC-MS (3 TMS) - 70eV, Positivesplash10-0059-1421009000-5e3bb6fefe16cfde53042017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erinacine D GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Erinacine D 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 - Erinacine D 10V, Positive-QTOFsplash10-004j-0009800000-01d5075d35d990e31af02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erinacine D 20V, Positive-QTOFsplash10-002b-0109000000-514e59c4ac9bbed7e2b32016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erinacine D 40V, Positive-QTOFsplash10-0v6s-3569100000-fc5faa17efb1a29f0a5e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erinacine D 10V, Negative-QTOFsplash10-004j-1106900000-28199b0d6681f2ed3dbb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erinacine D 20V, Negative-QTOFsplash10-0002-1239300000-c0b230194465e3205a072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erinacine D 40V, Negative-QTOFsplash10-014i-3029000000-4f36234ecf53b1fb72b22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erinacine D 10V, Negative-QTOFsplash10-004i-0000900000-2d8b8dd8350f5cf26c9c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erinacine D 20V, Negative-QTOFsplash10-0fba-2123900000-22210d2e063eb1335ac12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erinacine D 40V, Negative-QTOFsplash10-0zfv-7259500000-7ada49575b9ab98d1ecb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erinacine D 10V, Positive-QTOFsplash10-002b-0009400000-95875da88a0427df23812021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erinacine D 20V, Positive-QTOFsplash10-003i-1295500000-6f1ec853187281e0f6972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Erinacine D 40V, Positive-QTOFsplash10-07w9-9564000000-70bdb0afd1b09d5507602021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008581
KNApSAcK IDNot Available
Chemspider ID8088616
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9912965
PDB IDNot Available
ChEBI ID176162
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.