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Showing NP-Card for Synephrine (NP0083364)

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Record Information
Version2.0
Created at2022-04-29 04:24:22 UTC
Updated at2022-04-29 04:24:22 UTC
NP-MRD IDNP0083364
Secondary Accession NumbersNone
Natural Product Identification
Common NameSynephrine
DescriptionP-Synephrine, also known as (+/-)-synephrine or sympatol, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. P-Synephrine is a very strong basic compound (based on its pKa). Synephrine is found in Bergera koenegii, Citrus aurantium, Citrus aurantium L. var. amara , Citrus hassaku, Citrus limon, Citrus natsudaidai , Citrus reticulata, Citrus unshiu , Citrus sinensis , Ephedra sinica, Mammillaria longimamma, Zanthoxylum culantrillo and Zanthoxylum fagara. Synephrine was first documented in 1993 (PMID: 8255371). A phenethylamine alkaloid that is 4-(2-aminoethyl)phenol substituted by a hydroxy group at position 1 and a methyl group at the amino nitrogen (PMID: 17675045) (PMID: 18077120) (PMID: 23682231).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0083364 (Synephrine)


  Mrv0541 02231219592D          

 12 12  0  0  0  0            999 V2000
   20.6008  -15.3723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3153  -19.0848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0298  -14.5473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3153  -15.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0298  -15.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7443  -14.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3153  -18.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3153  -16.6098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6008  -17.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0298  -17.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6008  -17.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0298  -17.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  7  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  8 11  1  0  0  0  0
  8 12  2  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0083364 (Synephrine)

     RDKit          3D

 25 25  0  0  0  0  0  0  0  0999 V2000
   -2.9804    0.7281    1.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3274    0.8768   -0.0857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9094   -0.3406   -0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8103   -1.0812   -0.0257 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5990   -2.2479   -0.8062 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4872   -0.4269    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6836    0.9160   -0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9434    1.5135   -0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0165    0.7250    0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2894    1.2632    0.3626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8381   -0.6168    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5929   -1.1872    0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6846   -0.1219    1.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5819    1.6360    1.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1935    0.5570    1.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7419    1.5724   -0.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8079   -1.0279   -0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6945   -0.2468   -1.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1119   -1.4288    0.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4414   -3.0311   -0.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1191    1.5983   -0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583    2.5879   -0.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962    1.3107   -0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6848   -1.2572    0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5128   -2.2706    0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12  6  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  1
  5 20  1  0
  7 21  1  0
  8 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
M  END
Download

3D SDF for NP0083364 (Synephrine)


  Mrv0541 02231219592D          

 12 12  0  0  0  0            999 V2000
   20.6008  -15.3723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3153  -19.0848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0298  -14.5473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3153  -15.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0298  -15.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7443  -14.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3153  -18.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3153  -16.6098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6008  -17.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0298  -17.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6008  -17.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0298  -17.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  7  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  8 11  1  0  0  0  0
  8 12  2  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083364

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNCC(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

> <INCHI_KEY>
YRCWQPVGYLYSOX-UHFFFAOYSA-N

> <FORMULA>
C9H13NO2

> <MOLECULAR_WEIGHT>
167.205

> <EXACT_MASS>
167.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.22536589166284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[1-hydroxy-2-(methylamino)ethyl]phenol

> <ALOGPS_LOGP>
-0.62

> <JCHEM_LOGP>
-0.07095160063361274

> <ALOGPS_LOGS>
-0.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.270781477399648

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.755471273972516

> <JCHEM_PKA_STRONGEST_BASIC>
9.14815345799689

> <JCHEM_POLAR_SURFACE_AREA>
52.49

> <JCHEM_REFRACTIVITY>
47.24940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
synephrine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0083364 (Synephrine)

Download
PDB for NP0083364 (Synephrine)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      38.455 -28.695   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      39.789 -35.625   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      41.122 -27.155   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      39.789 -29.465   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      41.122 -28.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      42.456 -26.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      39.789 -34.085   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      39.789 -31.005   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      38.455 -33.315   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      41.122 -33.315   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      38.455 -31.775   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      41.122 -31.775   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    7                                                            
CONECT    3    5    6                                                       
CONECT    4    1    5    8                                                  
CONECT    5    3    4                                                       
CONECT    6    3                                                            
CONECT    7    2    9   10                                                  
CONECT    8    4   11   12                                                  
CONECT    9    7   11                                                       
CONECT   10    7   12                                                       
CONECT   11    8    9                                                       
CONECT   12    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Download
3D PDB for NP0083364 (Synephrine)
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SMILES for NP0083364 (Synephrine)
CNCC(O)C1=CC=C(O)C=C1
Download
INCHI for NP0083364 (Synephrine)
InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3
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View in JSmol
Synonyms
ValueSource
(+/-)-synephrineChEBI
1-(4-Hydroxyphenyl)-2-(methylamino)ethanolChEBI
1-(4-Hydroxyphenyl)-2-methylaminoethanolChEBI
4-Hydroxy-alpha-[(methylamino)methyl]benzenemethanolChEBI
beta-Methylamino-alpha-(4-hydroxyphenyl)ethyl alcoholChEBI
OxedrineChEBI
p-Hydroxy-alpha-[(methylamino)methyl]benzyl alcoholChEBI
SympatolChEBI
-SynephrineKegg
4-Hydroxy-a-[(methylamino)methyl]benzenemethanolGenerator
4-Hydroxy-α-[(methylamino)methyl]benzenemethanolGenerator
b-Methylamino-a-(4-hydroxyphenyl)ethyl alcoholGenerator
Β-methylamino-α-(4-hydroxyphenyl)ethyl alcoholGenerator
p-Hydroxy-a-[(methylamino)methyl]benzyl alcoholGenerator
p-Hydroxy-α-[(methylamino)methyl]benzyl alcoholGenerator
(+)-p-SynephrineHMDB
(+)-SynephrineHMDB
(+)-[(Methylamino)methyl]-benzenemethanoHMDB
AnaleptinHMDB
ParasympatolHMDB
SimpalonHMDB
SimpatolHMDB
SympaethaminHMDB
SympaethamineHMDB
SynephrineHMDB
SynephrinHMDB
Chemical FormulaC9H13NO2
Average Mass167.2050 Da
Monoisotopic Mass167.09463 Da
IUPAC Name4-[1-hydroxy-2-(methylamino)ethyl]phenol
Traditional Namesynephrine
CAS Registry NumberNot Available
SMILES
CNCC(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
InChI KeyYRCWQPVGYLYSOX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bergera koenegii-
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
Citrus aurantiumLOTUS Database
Citrus aurantium L. var. amaraPlant
Citrus hassakuLOTUS Database
Citrus limonLOTUS Database
Citrus natsudaidaiPlant
Citrus reticulataLOTUS Database
Citrus unshiuPlant
Citrus X sinensis (L.) Osbeck (pro. sp.)Plant
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Ephedra sinicaLOTUS Database
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Mammillaria longimammaLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Zanthoxylum culantrilloLOTUS Database
Zanthoxylum fagaraLOTUS Database
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.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub Class1-hydroxy-2-unsubstituted benzenoids  
Direct Parent1-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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.62ALOGPS
logP-0.071ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)9.76ChemAxon
pKa (Strongest Basic)9.15ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.25 m³·mol⁻¹ChemAxon
Polarizability18.23 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004826  
DrugBank IDDB09203  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001397  
KNApSAcK IDNot Available
Chemspider ID6904  
KEGG Compound IDC04548  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSynephrine  
METLIN ID7088  
PubChem Compound7172  
PDB IDNot Available
ChEBI ID29081  
Good Scents IDNot Available
References
General References
  1. 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  ] 
  2. Pellati F, Benvenuti S: Fast high-performance liquid chromatography analysis of phenethylamine alkaloids in Citrus natural products on a pentafluorophenylpropyl stationary phase. J Chromatogr A. 2007 Sep 21;1165(1-2):58-66. doi: 10.1016/j.chroma.2007.07.041. Epub 2007 Jul 25. [PubMed:17675045  ] 
  3. Pellati F, Benvenuti S: Determination of ephedrine alkaloids in Ephedra natural products using HPLC on a pentafluorophenylpropyl stationary phase. J Pharm Biomed Anal. 2008 Sep 29;48(2):254-63. doi: 10.1016/j.jpba.2007.10.034. Epub 2007 Nov 6. [PubMed:18077120  ] 
  4. Chung H, Kwon SW, Kim TH, Yoon JH, Ma DW, Park YM, Hong BK: Synephrine-containing dietary supplement precipitating apical ballooning syndrome in a young female. Korean J Intern Med. 2013 May;28(3):356-60. doi: 10.3904/kjim.2013.28.3.356. Epub 2013 May 1. [PubMed:23682231  ]