NP-MRD: Showing NP-Card for ( )-synephrine (NP0323918)

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Record Information

Version

1.0

Created at

2022-09-12 03:39:30 UTC

Updated at

2022-09-12 03:39:30 UTC

NP-MRD ID

NP0323918

Secondary Accession Numbers

None

Natural Product Identification

Common Name

( )-synephrine

Description

D-synephrine belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. ( )-synephrine is found in Citrus reshni, Mammillaria longimamma, Zanthoxylum culantrillo and Zanthoxylum fagara. It was first documented in 1993 (PMID: 8255371). D-synephrine is a very strong basic compound (based on its pKa) (PMID: 8833327).

Structure

MOL 3D MOL SDF 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

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 Mass

167.2080 Da

Monoisotopic Mass

167.09463 Da

IUPAC Name

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

Traditional Name

( )-synephrine

CAS Registry Number

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Citrus reshni	LOTUS Database	35616633
Mammillaria longimamma	LOTUS Database	35616633
Zanthoxylum culantrillo	LOTUS Database	35616633
Zanthoxylum fagara	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0062811

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Andrew R, Best SA, Watson DG, Midgley JM, Reid JL, Squire IB: Analysis of biogenic amines in plasma of hypertensive patients and a control group. Neurochem Res. 1993 Nov;18(11):1179-82. doi: 10.1007/BF00978371. [PubMed:8255371 ]
Kusu F, Matsumoto K, Arai K, Takamura K: Determination of synephrine enantiomers in food and conjugated synephrine in urine by high-performance liquid chromatography with electrochemical detection. Anal Biochem. 1996 Mar 15;235(2):191-4. doi: 10.1006/abio.1996.0111. [PubMed:8833327 ]
LOTUS database [Link]

Showing NP-Card for ( )-synephrine (NP0323918)

MOL for NP0323918 (( )-synephrine)

3D MOL for NP0323918 (( )-synephrine)

3D SDF for NP0323918 (( )-synephrine)

3D-SDF for NP0323918 (( )-synephrine)

PDB for NP0323918 (( )-synephrine)

3D PDB for NP0323918 (( )-synephrine)

SMILES for NP0323918 (( )-synephrine)

INCHI for NP0323918 (( )-synephrine)

Structure for NP0323918 (( )-synephrine)

3D Structure for NP0323918 (( )-synephrine)