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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:16 UTC

Update Date

2023-02-21 17:21:28 UTC

HMDB ID

HMDB0032020

Secondary Accession Numbers

HMDB0041888
HMDB32020
HMDB41888

Metabolite Identification

Common Name

Epinine

Description

Epinine, 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 17-APR-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-18         0                                  
HETATM    1  C   UNK     0    8667.2958668.205   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.6298667.435   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8669.9608668.205   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8671.2948667.435   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8661.9648668.205   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8661.9648665.129   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8665.9658667.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.6318668.207   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.2978667.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.2978665.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.6318665.127   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.9658665.897   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    9                                                            
CONECT    6   10                                                            
CONECT    7    8   12    1                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10    5                                                  
CONECT   10    9   11    6                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Deoxyepinephrine	Kegg
4-(b-Methylaminoethyl)catechol	HMDB
4-(Β-methylaminoethyl)catechol	HMDB
Deoxyadrenaline	HMDB
Methyldopamine	HMDB
4-(2-(Methylamino)ethyl)-1,2-benzenediol	HMDB
4-(2-Methylaminoethyl)pyrocatechol	HMDB
4-[2-(Methylamino)ethyl]-1,2-benzenediol	HMDB
4-[2-(Methylamino)ethyl]-1,2-benzenediol, 9ci	HMDB
4-[2-(Methylamino)ethyl]pyrocatechol, 8ci	HMDB
N-Methyl-2-(3,4-dihydroxyphenyl)ethylamine	HMDB
N-Methyldopamine	HMDB
N-Methyldopamine hydrochloride	HMDB
1-(3,4-Dihydroxyphenyl)-2-methylaminoethane	HMDB
3,4-Dihydroxy-N-methylphenethylamine	HMDB
4-(2-Methylamino-ethyl)-benzene-1,2-diol	HMDB
Epinin	HMDB
Epyamine	HMDB
N-Methyl-3,4-dihydroxyphenethylamine	HMDB
4-(beta-Methylaminoethyl)catechol	HMDB
Epinine	HMDB

Chemical Formula

C₉H₁₃NO₂

Average Molecular Weight

167.205

Monoisotopic Molecular Weight

167.094628665

IUPAC Name

4-[2-(methylamino)ethyl]benzene-1,2-diol

Traditional Name

methyldopamine

CAS Registry Number

501-15-5

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 Key

NGKZFDYBISXGGS-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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Catecholamines 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

catecholamine (CHEBI:10554 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0041888)
Extracellular (HMDB: HMDB0041888)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041888)

Source

Endogenous

Endogenous (HMDB: HMDB0041888)

Plant

Fabaceae (HMDB: HMDB0041888)

Exogenous

Food

Food (HMDB: HMDB0041888)

Pulse

Pulses (FooDB: FOOD00867)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041888)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	188 - 189 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.28 g/L	ALOGPS
logP	0.03	ALOGPS
logP	0.32	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	9.27	ChemAxon
pKa (Strongest Basic)	10.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	52.49 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.02 m³·mol⁻¹	ChemAxon
Polarizability	18.29 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.352	31661259
DarkChem	[M-H]-	134.823	31661259
DeepCCS	[M+H]+	138.346	30932474
DeepCCS	[M-H]-	134.516	30932474
DeepCCS	[M-2H]-	172.187	30932474
DeepCCS	[M+Na]+	147.726	30932474
AllCCS	[M+H]+	137.0	32859911
AllCCS	[M+H-H2O]+	132.7	32859911
AllCCS	[M+NH4]+	141.1	32859911
AllCCS	[M+Na]+	142.2	32859911
AllCCS	[M-H]-	138.0	32859911
AllCCS	[M+Na-2H]-	139.2	32859911
AllCCS	[M+HCOO]-	140.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Epinine	CNCCC1=CC(O)=C(O)C=C1	2726.0	Standard polar	33892256
Epinine	CNCCC1=CC(O)=C(O)C=C1	1661.2	Standard non polar	33892256
Epinine	CNCCC1=CC(O)=C(O)C=C1	1612.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Epinine,1TMS,isomer #1	CNCCC1=CC=C(O)C(O[Si](C)(C)C)=C1	1618.8	Semi standard non polar	33892256
Epinine,1TMS,isomer #2	CNCCC1=CC=C(O[Si](C)(C)C)C(O)=C1	1628.0	Semi standard non polar	33892256
Epinine,1TMS,isomer #3	CN(CCC1=CC=C(O)C(O)=C1)[Si](C)(C)C	1869.0	Semi standard non polar	33892256
Epinine,2TMS,isomer #1	CNCCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1683.2	Semi standard non polar	33892256
Epinine,2TMS,isomer #2	CN(CCC1=CC=C(O)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	1823.6	Semi standard non polar	33892256
Epinine,2TMS,isomer #3	CN(CCC1=CC=C(O[Si](C)(C)C)C(O)=C1)[Si](C)(C)C	1838.0	Semi standard non polar	33892256
Epinine,3TMS,isomer #1	CN(CCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	1895.0	Semi standard non polar	33892256
Epinine,3TMS,isomer #1	CN(CCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	1892.7	Standard non polar	33892256
Epinine,1TBDMS,isomer #1	CNCCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	1872.5	Semi standard non polar	33892256
Epinine,1TBDMS,isomer #2	CNCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	1887.3	Semi standard non polar	33892256
Epinine,1TBDMS,isomer #3	CN(CCC1=CC=C(O)C(O)=C1)[Si](C)(C)C(C)(C)C	2081.7	Semi standard non polar	33892256
Epinine,2TBDMS,isomer #1	CNCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2164.0	Semi standard non polar	33892256
Epinine,2TBDMS,isomer #2	CN(CCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2315.0	Semi standard non polar	33892256
Epinine,2TBDMS,isomer #3	CN(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)[Si](C)(C)C(C)(C)C	2337.5	Semi standard non polar	33892256
Epinine,3TBDMS,isomer #1	CN(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)C	2613.7	Semi standard non polar	33892256
Epinine,3TBDMS,isomer #1	CN(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)C	2553.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Epinine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-49fcce0872e018334c7f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epinine GC-MS (2 TMS) - 70eV, Positive	splash10-0006-9050000000-a94c549c57320f95f176	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epinine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epinine LC-ESI-QQ , positive-QTOF	splash10-014i-0900000000-af3f6b2fb280237cf053	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epinine LC-ESI-QQ , positive-QTOF	splash10-000i-1900000000-21c649b827452d6216d6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epinine LC-ESI-QQ , positive-QTOF	splash10-0006-9600000000-d1e968124aaf320bcffc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epinine LC-ESI-QQ , positive-QTOF	splash10-0006-9000000000-f1d18ccffad64909d3a7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epinine LC-ESI-QQ , positive-QTOF	splash10-00kf-9000000000-90d7d2c007015685d34e	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epinine 10V, Positive-QTOF	splash10-014r-0900000000-aab37a71d5dcc697be35	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epinine 20V, Positive-QTOF	splash10-00kr-2900000000-f3e3687a2591c99d2228	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epinine 40V, Positive-QTOF	splash10-1029-9500000000-8ed72cee197b39eef631	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epinine 10V, Negative-QTOF	splash10-014i-0900000000-b538f8f6eb94b9c86d43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epinine 20V, Negative-QTOF	splash10-014i-1900000000-3b7c25cfd78606c8e0af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epinine 40V, Negative-QTOF	splash10-05gr-4900000000-fad9b7db3beebbb7b311	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epinine 10V, Negative-QTOF	splash10-014i-0900000000-104aad9eca02be4778f8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epinine 20V, Negative-QTOF	splash10-014i-0900000000-e8f7c27c3d41479ce1ae	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epinine 40V, Negative-QTOF	splash10-00r6-9600000000-40781455f7a3cfc21718	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epinine 10V, Positive-QTOF	splash10-000i-0900000000-17d243c562303c62ed05	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epinine 20V, Positive-QTOF	splash10-0670-2900000000-46bf0c13dd55e794bafc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epinine 40V, Positive-QTOF	splash10-066r-9700000000-c0472360644761657164	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Deoxyepinephrine

METLIN ID

Not Available

PubChem Compound

4382

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Epinine (HMDB0032020)

MOL for HMDB0032020 (Epinine)

3D MOL for HMDB0032020 (Epinine)

3D SDF for HMDB0032020 (Epinine)

3D-SDF for HMDB0032020 (Epinine)

PDB for HMDB0032020 (Epinine)

3D PDB for HMDB0032020 (Epinine)

SMILES for HMDB0032020 (Epinine)

INCHI for HMDB0032020 (Epinine)

Structure for HMDB0032020 (Epinine)

3D Structure for HMDB0032020 (Epinine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra