Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-23 06:28:26 UTC

Update Date

2022-03-07 03:18:00 UTC

HMDB ID

HMDB0062811

Secondary Accession Numbers

HMDB62811

Metabolite Identification

Common Name

D-synephrine

Description

D-synephrine, also known as (-)-Oxedrine or (-)-Sympatol, is classified as a member of the 1-hydroxy-2-unsubstituted benzenoids. 1-hydroxy-2-unsubstituted benzenoids are phenols that a unsubstituted at the 2-position. D-synephrine is considered to be soluble (in water) and acidic

Structure

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

HEADER    PROTEIN                                 08-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-JUN-15         0                                  
HETATM    1  C   UNK     0      39.899 -30.686   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      39.899 -32.169   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      41.227 -29.905   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      38.572 -29.905   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      38.572 -32.950   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      41.227 -32.950   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      41.227 -28.343   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      38.572 -28.343   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      37.245 -32.169   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      39.899 -27.563   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      35.917 -33.497   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      39.899 -26.001   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2                                                            
CONECT    7    3   10                                                       
CONECT    8    4   10                                                       
CONECT    9    5   11                                                       
CONECT   10    7   12    8                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
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
(-)-4-Hydroxy-alpha-[(methylamino)methyl]benzenemethanol	ChEBI
(-)-Oxedrine	ChEBI
(-)-p-Hydroxy-alpha-[(methylamino)methyl]benzyl alcohol	ChEBI
(-)-Synephrine	ChEBI
(-)-Sympatol	ChEBI
D(-)-Synephrine	ChEBI
(R)-Synephrine	Kegg
(-)-4-Hydroxy-a-[(methylamino)methyl]benzenemethanol	Generator
(-)-4-Hydroxy-α-[(methylamino)methyl]benzenemethanol	Generator
(-)-p-Hydroxy-a-[(methylamino)methyl]benzyl alcohol	Generator
(-)-p-Hydroxy-α-[(methylamino)methyl]benzyl alcohol	Generator

Chemical Formula

C₉H₁₃NO₂

Average Molecular Weight

167.208

Monoisotopic Molecular Weight

167.094628663

IUPAC Name

4-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol

Traditional Name

( )-synephrine

CAS Registry Number

614-35-7

SMILES

CNC[C@H](O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1

InChI Key

YRCWQPVGYLYSOX-VIFPVBQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

synephrine (CHEBI:119 )

Ontology

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	18.6 g/l	ALOGPS
LogP	-0.62	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.62	ALOGPS
logP	-0.071	ChemAxon
logS	-0.95	ALOGPS
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	9.15	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	47.25 m³·mol⁻¹	ChemAxon
Polarizability	18.25 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]+	140.617	31661259
DarkChem	[M-H]-	134.953	31661259
DeepCCS	[M+H]+	137.659	30932474
DeepCCS	[M-H]-	134.846	30932474
DeepCCS	[M-2H]-	170.987	30932474
DeepCCS	[M+Na]+	146.525	30932474
AllCCS	[M+H]+	137.8	32859911
AllCCS	[M+H-H2O]+	133.5	32859911
AllCCS	[M+NH4]+	141.9	32859911
AllCCS	[M+Na]+	143.0	32859911
AllCCS	[M-H]-	138.1	32859911
AllCCS	[M+Na-2H]-	139.3	32859911
AllCCS	[M+HCOO]-	140.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
D-synephrine	CNC[C@H](O)C1=CC=C(O)C=C1	2689.3	Standard polar	33892256
D-synephrine	CNC[C@H](O)C1=CC=C(O)C=C1	1642.2	Standard non polar	33892256
D-synephrine	CNC[C@H](O)C1=CC=C(O)C=C1	1672.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
D-synephrine,1TMS,isomer #1	CNC[C@H](O[Si](C)(C)C)C1=CC=C(O)C=C1	1745.2	Semi standard non polar	33892256
D-synephrine,1TMS,isomer #2	CNC[C@H](O)C1=CC=C(O[Si](C)(C)C)C=C1	1677.5	Semi standard non polar	33892256
D-synephrine,1TMS,isomer #3	CN(C[C@H](O)C1=CC=C(O)C=C1)[Si](C)(C)C	1811.7	Semi standard non polar	33892256
D-synephrine,2TMS,isomer #1	CNC[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1	1663.1	Semi standard non polar	33892256
D-synephrine,2TMS,isomer #2	CN(C[C@H](O[Si](C)(C)C)C1=CC=C(O)C=C1)[Si](C)(C)C	1861.0	Semi standard non polar	33892256
D-synephrine,2TMS,isomer #3	CN(C[C@H](O)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	1839.1	Semi standard non polar	33892256
D-synephrine,3TMS,isomer #1	CN(C[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	1834.5	Semi standard non polar	33892256
D-synephrine,3TMS,isomer #1	CN(C[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	1818.5	Standard non polar	33892256
D-synephrine,3TMS,isomer #1	CN(C[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	1846.1	Standard polar	33892256
D-synephrine,1TBDMS,isomer #1	CNC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C1	1970.7	Semi standard non polar	33892256
D-synephrine,1TBDMS,isomer #2	CNC[C@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	1927.9	Semi standard non polar	33892256
D-synephrine,1TBDMS,isomer #3	CN(C[C@H](O)C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	2034.5	Semi standard non polar	33892256
D-synephrine,2TBDMS,isomer #1	CNC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2137.2	Semi standard non polar	33892256
D-synephrine,2TBDMS,isomer #2	CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	2334.5	Semi standard non polar	33892256
D-synephrine,2TBDMS,isomer #3	CN(C[C@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2346.2	Semi standard non polar	33892256
D-synephrine,3TBDMS,isomer #1	CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2560.1	Semi standard non polar	33892256
D-synephrine,3TBDMS,isomer #1	CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2470.3	Standard non polar	33892256
D-synephrine,3TBDMS,isomer #1	CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2239.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - D-synephrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-0b89ec1502bbf0bb1879	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-synephrine GC-MS (2 TMS) - 70eV, Positive	splash10-006x-9150000000-b5f2dbddba7baed4d774	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-synephrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-synephrine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-synephrine 10V, Positive-QTOF	splash10-0uxr-0900000000-63ab15460551b5c90867	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-synephrine 20V, Positive-QTOF	splash10-0uxr-0900000000-5a26ad0ce3c3f5a25608	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-synephrine 40V, Positive-QTOF	splash10-0aor-6900000000-9a0f0e1fecffa43dcfdb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-synephrine 10V, Negative-QTOF	splash10-014i-0900000000-8561535681faf138ceea	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-synephrine 20V, Negative-QTOF	splash10-014j-2900000000-59329a14b178ca50c0b1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-synephrine 40V, Negative-QTOF	splash10-0006-9300000000-040c43b57212bf81ad8a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-synephrine 10V, Negative-QTOF	splash10-014i-1900000000-832cda2fe5651203ce37	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-synephrine 20V, Negative-QTOF	splash10-0avl-2900000000-6a789e30e9999b4391e7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-synephrine 40V, Negative-QTOF	splash10-014l-6900000000-2944a38d623d1305021c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-synephrine 10V, Positive-QTOF	splash10-0udi-0900000000-59284684d3d1f5845efb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-synephrine 20V, Positive-QTOF	splash10-0q29-1900000000-eccd6882ea86aed6f824	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-synephrine 40V, Positive-QTOF	splash10-0a4i-7900000000-2f829c6bfc720e526453	2021-09-24	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

Biological Properties

Cellular Locations

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C01869

BioCyc ID

1-4-HYDROXYPHENYL-2-METHYLAMINOETHAN

BiGG ID

Not Available

Wikipedia Link

Synephrine

METLIN ID

Not Available

PubChem Compound

854067

PDB ID

Not Available

ChEBI ID

119

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

Not Available

Showing metabocard for D-synephrine (HMDB0062811)

MOL for HMDB0062811 (D-synephrine)

3D MOL for HMDB0062811 (D-synephrine)

3D SDF for HMDB0062811 (D-synephrine)

3D-SDF for HMDB0062811 (D-synephrine)

PDB for HMDB0062811 (D-synephrine)

3D PDB for HMDB0062811 (D-synephrine)

SMILES for HMDB0062811 (D-synephrine)

INCHI for HMDB0062811 (D-synephrine)

Structure for HMDB0062811 (D-synephrine)

3D Structure for HMDB0062811 (D-synephrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra