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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:29:06 UTC

Update Date

2021-09-26 23:08:10 UTC

HMDB ID

HMDB0254276

Secondary Accession Numbers

None

Metabolite Identification

Common Name

m-Hydroxyephedrine

Description

m-Hydroxyephedrine belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Based on a literature review a small amount of articles have been published on m-Hydroxyephedrine. This compound has been identified in human blood as reported by (PMID: 31557052 ). M-hydroxyephedrine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically m-Hydroxyephedrine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       0.000   6.160   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    6                                                            
CONECT   11    3                                                            
CONECT   12    2   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0254276
HETATM    1  C1  UNL     1      -3.250   0.635   0.464  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.830  -0.020  -0.749  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.497  -0.590  -0.512  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.647  -1.606   0.563  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.551   0.521  -0.260  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.543   1.433  -1.359  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.866   0.164  -0.075  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.270  -1.130  -0.088  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.634  -1.381   0.113  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.499  -0.336   0.313  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.103   0.981   0.328  1.00  0.00           C  
HETATM   12  O2  UNL     1       4.027   1.996   0.535  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.758   1.209   0.129  1.00  0.00           C  
HETATM   14  H1  UNL     1      -3.333   1.734   0.284  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.595   0.419   1.307  1.00  0.00           H  
HETATM   16  H3  UNL     1      -4.286   0.277   0.717  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.775   0.672  -1.550  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.200  -1.108  -1.446  1.00  0.00           H  
HETATM   19  H6  UNL     1      -2.696  -1.542   0.982  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.585  -2.670   0.219  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.994  -1.501   1.434  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.888   1.164   0.590  1.00  0.00           H  
HETATM   23  H10 UNL     1      -0.587   0.889  -2.195  1.00  0.00           H  
HETATM   24  H11 UNL     1       0.601  -1.989  -0.258  1.00  0.00           H  
HETATM   25  H12 UNL     1       2.954  -2.409   0.103  1.00  0.00           H  
HETATM   26  H13 UNL     1       4.572  -0.522   0.472  1.00  0.00           H  
HETATM   27  H14 UNL     1       4.536   2.460  -0.200  1.00  0.00           H  
HETATM   28  H15 UNL     1       1.439   2.249   0.140  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17
CONECT    3    4    5   18
CONECT    4   19   20   21
CONECT    5    6    7   22
CONECT    6   23
CONECT    7    8    8   13
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   11   26
CONECT   11   12   13   13
CONECT   12   27
CONECT   13   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
11C-Hydroxyephedrine-meta	HMDB
11C-Meta-hydroxyephedrine	HMDB
HCL(R-(R,s))-isomer OF 3-hydroxyephedrine	HMDB
R-(R,s)-isomer OF 3-hydroxyephedrine	HMDB
Meta-hydroxyephedrine	HMDB

Chemical Formula

C₁₀H₁₅NO₂

Average Molecular Weight

181.235

Monoisotopic Molecular Weight

181.110278727

IUPAC Name

3-[1-hydroxy-2-(methylamino)propyl]phenol

Traditional Name

3-[1-hydroxy-2-(methylamino)propyl]phenol

CAS Registry Number

Not Available

SMILES

CNC(C)C(O)C1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C10H15NO2/c1-7(11-2)10(13)8-4-3-5-9(12)6-8/h3-7,10-13H,1-2H3

InChI Key

KEEFJRKWMCQJLN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
1,2-aminoalcohol
Secondary alcohol
Secondary aliphatic amine
Secondary amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Alcohol
Aromatic alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.13	ALOGPS
logP	0.29	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	9.11	ChemAxon
pKa (Strongest Basic)	9.74	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	51.67 m³·mol⁻¹	ChemAxon
Polarizability	19.95 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
DeepCCS	[M+H]+	138.738	30932474
DeepCCS	[M-H]-	136.127	30932474
DeepCCS	[M-2H]-	172.326	30932474
DeepCCS	[M+Na]+	147.864	30932474
AllCCS	[M+H]+	143.7	32859911
AllCCS	[M+H-H2O]+	139.7	32859911
AllCCS	[M+NH4]+	147.5	32859911
AllCCS	[M+Na]+	148.6	32859911
AllCCS	[M-H]-	141.2	32859911
AllCCS	[M+Na-2H]-	142.3	32859911
AllCCS	[M+HCOO]-	143.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
m-Hydroxyephedrine	CNC(C)C(O)C1=CC(O)=CC=C1	2878.5	Standard polar	33892256
m-Hydroxyephedrine	CNC(C)C(O)C1=CC(O)=CC=C1	1649.1	Standard non polar	33892256
m-Hydroxyephedrine	CNC(C)C(O)C1=CC(O)=CC=C1	1728.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
m-Hydroxyephedrine,3TMS,isomer #1	CC(C(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1)N(C)[Si](C)(C)C	1810.2	Semi standard non polar	33892256
m-Hydroxyephedrine,3TMS,isomer #1	CC(C(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1)N(C)[Si](C)(C)C	1789.7	Standard non polar	33892256
m-Hydroxyephedrine,3TMS,isomer #1	CC(C(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1)N(C)[Si](C)(C)C	1838.2	Standard polar	33892256
m-Hydroxyephedrine,3TBDMS,isomer #1	CC(C(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)N(C)[Si](C)(C)C(C)(C)C	2509.6	Semi standard non polar	33892256
m-Hydroxyephedrine,3TBDMS,isomer #1	CC(C(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)N(C)[Si](C)(C)C(C)(C)C	2430.1	Standard non polar	33892256
m-Hydroxyephedrine,3TBDMS,isomer #1	CC(C(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)N(C)[Si](C)(C)C(C)(C)C	2220.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxyephedrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9200000000-fb7980c9cd815ecb56cd	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxyephedrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxyephedrine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxyephedrine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxyephedrine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxyephedrine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxyephedrine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxyephedrine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxyephedrine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxyephedrine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxyephedrine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxyephedrine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxyephedrine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxyephedrine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Hydroxyephedrine 10V, Positive-QTOF	splash10-03di-0900000000-7194e62c28ca536484f4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Hydroxyephedrine 20V, Positive-QTOF	splash10-08gi-0900000000-6fcebbe528ed1b7101a0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Hydroxyephedrine 40V, Positive-QTOF	splash10-0a4i-5900000000-d27d53f76e17d8f725ef	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Hydroxyephedrine 10V, Negative-QTOF	splash10-06si-0900000000-ae9168c2c09be6509101	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Hydroxyephedrine 20V, Negative-QTOF	splash10-001i-0900000000-701dfbaa747e415c3e07	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Hydroxyephedrine 40V, Negative-QTOF	splash10-0006-9400000000-75e067f71d250107049b	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17141

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18147

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for m-Hydroxyephedrine (HMDB0254276)

MOL for HMDB0254276 (m-Hydroxyephedrine)

3D MOL for HMDB0254276 (m-Hydroxyephedrine)

3D SDF for HMDB0254276 (m-Hydroxyephedrine)

3D-SDF for HMDB0254276 (m-Hydroxyephedrine)

PDB for HMDB0254276 (m-Hydroxyephedrine)

3D PDB for HMDB0254276 (m-Hydroxyephedrine)

SMILES for HMDB0254276 (m-Hydroxyephedrine)

INCHI for HMDB0254276 (m-Hydroxyephedrine)

Structure for HMDB0254276 (m-Hydroxyephedrine)

3D Structure for HMDB0254276 (m-Hydroxyephedrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra