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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:16 UTC
Update Date2023-02-21 17:21:28 UTC
HMDB IDHMDB0032020
Secondary Accession Numbers
  • HMDB0041888
  • HMDB32020
  • HMDB41888
Metabolite Identification
Common NameEpinine
DescriptionEpinine, also known as deoxyepinephrine or deoxyadrenaline, is a member of the class of compounds known as catecholamines and derivatives. These compounds contain 4-(2-aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution. Epinine exists as a solid, and is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Epinine is an alkaloid from Vicia faba and can be found in pulses. Epinine is a dopamine and epinephrine derivative.
Structure
Data?1677000088
Synonyms
ValueSource
DeoxyepinephrineKegg
4-(b-Methylaminoethyl)catecholHMDB
4-(Β-methylaminoethyl)catecholHMDB
DeoxyadrenalineHMDB
MethyldopamineHMDB
4-(2-(Methylamino)ethyl)-1,2-benzenediolHMDB
4-(2-Methylaminoethyl)pyrocatecholHMDB
4-[2-(Methylamino)ethyl]-1,2-benzenediolHMDB
4-[2-(Methylamino)ethyl]-1,2-benzenediol, 9ciHMDB
4-[2-(Methylamino)ethyl]pyrocatechol, 8ciHMDB
N-Methyl-2-(3,4-dihydroxyphenyl)ethylamineHMDB
N-MethyldopamineHMDB
N-Methyldopamine hydrochlorideHMDB
1-(3,4-Dihydroxyphenyl)-2-methylaminoethaneHMDB
3,4-Dihydroxy-N-methylphenethylamineHMDB
4-(2-Methylamino-ethyl)-benzene-1,2-diolHMDB
EpininHMDB
EpyamineHMDB
N-Methyl-3,4-dihydroxyphenethylamineHMDB
4-(beta-Methylaminoethyl)catecholHMDB
EpinineHMDB
Chemical FormulaC9H13NO2
Average Molecular Weight167.205
Monoisotopic Molecular Weight167.094628665
IUPAC Name4-[2-(methylamino)ethyl]benzene-1,2-diol
Traditional Namemethyldopamine
CAS Registry Number501-15-5
SMILES
CNCCC1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C9H13NO2/c1-10-5-4-7-2-3-8(11)9(12)6-7/h2-3,6,10-12H,4-5H2,1H3
InChI KeyNGKZFDYBISXGGS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catecholamines and derivatives. Catecholamines and derivatives are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatecholamines and derivatives
Alternative Parents
Substituents
  • Catecholamine
  • Phenethylamine
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • Secondary aliphatic amine
  • Secondary amine
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point188 - 189 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.28 g/LALOGPS
logP0.03ALOGPS
logP0.32ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.27ChemAxon
pKa (Strongest Basic)10.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.02 m³·mol⁻¹ChemAxon
Polarizability18.29 ųChemAxon
Number of Rings1ChemAxon
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]+137.35231661259
DarkChem[M-H]-134.82331661259
DeepCCS[M+H]+138.34630932474
DeepCCS[M-H]-134.51630932474
DeepCCS[M-2H]-172.18730932474
DeepCCS[M+Na]+147.72630932474
AllCCS[M+H]+137.032859911
AllCCS[M+H-H2O]+132.732859911
AllCCS[M+NH4]+141.132859911
AllCCS[M+Na]+142.232859911
AllCCS[M-H]-138.032859911
AllCCS[M+Na-2H]-139.232859911
AllCCS[M+HCOO]-140.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EpinineCNCCC1=CC(O)=C(O)C=C12726.0Standard polar33892256
EpinineCNCCC1=CC(O)=C(O)C=C11661.2Standard non polar33892256
EpinineCNCCC1=CC(O)=C(O)C=C11612.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Epinine,1TMS,isomer #1CNCCC1=CC=C(O)C(O[Si](C)(C)C)=C11618.8Semi standard non polar33892256
Epinine,1TMS,isomer #2CNCCC1=CC=C(O[Si](C)(C)C)C(O)=C11628.0Semi standard non polar33892256
Epinine,1TMS,isomer #3CN(CCC1=CC=C(O)C(O)=C1)[Si](C)(C)C1869.0Semi standard non polar33892256
Epinine,2TMS,isomer #1CNCCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11683.2Semi standard non polar33892256
Epinine,2TMS,isomer #2CN(CCC1=CC=C(O)C(O[Si](C)(C)C)=C1)[Si](C)(C)C1823.6Semi standard non polar33892256
Epinine,2TMS,isomer #3CN(CCC1=CC=C(O[Si](C)(C)C)C(O)=C1)[Si](C)(C)C1838.0Semi standard non polar33892256
Epinine,3TMS,isomer #1CN(CCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[Si](C)(C)C1895.0Semi standard non polar33892256
Epinine,3TMS,isomer #1CN(CCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[Si](C)(C)C1892.7Standard non polar33892256
Epinine,1TBDMS,isomer #1CNCCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C11872.5Semi standard non polar33892256
Epinine,1TBDMS,isomer #2CNCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C11887.3Semi standard non polar33892256
Epinine,1TBDMS,isomer #3CN(CCC1=CC=C(O)C(O)=C1)[Si](C)(C)C(C)(C)C2081.7Semi standard non polar33892256
Epinine,2TBDMS,isomer #1CNCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12164.0Semi standard non polar33892256
Epinine,2TBDMS,isomer #2CN(CCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C2315.0Semi standard non polar33892256
Epinine,2TBDMS,isomer #3CN(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)[Si](C)(C)C(C)(C)C2337.5Semi standard non polar33892256
Epinine,3TBDMS,isomer #1CN(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C2613.7Semi standard non polar33892256
Epinine,3TBDMS,isomer #1CN(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C2553.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Epinine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-49fcce0872e018334c7f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epinine GC-MS (2 TMS) - 70eV, Positivesplash10-0006-9050000000-a94c549c57320f95f1762017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epinine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Epinine LC-ESI-QQ , positive-QTOFsplash10-014i-0900000000-af3f6b2fb280237cf0532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epinine LC-ESI-QQ , positive-QTOFsplash10-000i-1900000000-21c649b827452d6216d62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epinine LC-ESI-QQ , positive-QTOFsplash10-0006-9600000000-d1e968124aaf320bcffc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epinine LC-ESI-QQ , positive-QTOFsplash10-0006-9000000000-f1d18ccffad64909d3a72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epinine LC-ESI-QQ , positive-QTOFsplash10-00kf-9000000000-90d7d2c007015685d34e2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinine 10V, Positive-QTOFsplash10-014r-0900000000-aab37a71d5dcc697be352016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinine 20V, Positive-QTOFsplash10-00kr-2900000000-f3e3687a2591c99d22282016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinine 40V, Positive-QTOFsplash10-1029-9500000000-8ed72cee197b39eef6312016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinine 10V, Negative-QTOFsplash10-014i-0900000000-b538f8f6eb94b9c86d432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinine 20V, Negative-QTOFsplash10-014i-1900000000-3b7c25cfd78606c8e0af2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinine 40V, Negative-QTOFsplash10-05gr-4900000000-fad9b7db3beebbb7b3112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinine 10V, Negative-QTOFsplash10-014i-0900000000-104aad9eca02be4778f82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinine 20V, Negative-QTOFsplash10-014i-0900000000-e8f7c27c3d41479ce1ae2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinine 40V, Negative-QTOFsplash10-00r6-9600000000-40781455f7a3cfc217182021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinine 10V, Positive-QTOFsplash10-000i-0900000000-17d243c562303c62ed052021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinine 20V, Positive-QTOFsplash10-0670-2900000000-46bf0c13dd55e794bafc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epinine 40V, Positive-QTOFsplash10-066r-9700000000-c04723606447616571642021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB008718
KNApSAcK IDC00042777
Chemspider ID4229
KEGG Compound IDC07453
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDeoxyepinephrine
METLIN IDNot Available
PubChem Compound4382
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .