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Showing NP-Card for (-)-norephedrine (NP0270570)

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Record Information
Version2.0
Created at2022-09-08 16:33:41 UTC
Updated at2022-09-08 16:33:41 UTC
NP-MRD IDNP0270570
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-norephedrine
Description(-)-Norephedrine, also known as phenylpropanolamine or triaminic DM, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety (-)-norephedrine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (-)-norephedrine is found in Catha edulis, Ephedra distachya and Ephedra sinica. (-)-norephedrine was first documented in 1992 (PMID: 1639915). Based on a literature review a small amount of articles have been published on (-)-norephedrine (PMID: 14750795) (PMID: 20417943) (PMID: 21924876) (PMID: 22215969).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0270570 ((-)-norephedrine)


  Mrv1652309082218332D          

 11 11  0  0  1  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
M  END
Download

3D MOL for NP0270570 ((-)-norephedrine)

     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.0947    0.9987    0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7301   -0.3024   -0.2937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8309   -1.2310    0.0202 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4936   -0.9362    0.2914 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6975   -1.0700    1.6636 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7506   -0.2610   -0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1896    0.8844    0.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3753    1.4927    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1509    0.9489   -0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7352   -0.1949   -1.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5490   -0.7727   -1.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668    0.9668    1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6683    1.8374   -0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2129    1.1528    0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6742   -0.1959   -1.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6857   -0.9089   -0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9290   -1.3198    1.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4605   -1.9708   -0.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5088   -1.9833    1.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6046    1.3340    1.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7165    2.3843    0.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0704    1.4500   -1.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3431   -0.6203   -2.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2678   -1.6826   -1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  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
 10 11  2  0
 11  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  6
  3 16  1  0
  3 17  1  0
  4 18  1  6
  5 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
M  END
Download

3D SDF for NP0270570 ((-)-norephedrine)


  Mrv1652309082218332D          

 11 11  0  0  1  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0270570

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](N)[C@H](O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1

> <INCHI_KEY>
DLNKOYKMWOXYQA-CBAPKCEASA-N

> <FORMULA>
C9H13NO

> <MOLECULAR_WEIGHT>
151.209

> <EXACT_MASS>
151.099714043

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.89489745963767

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S)-2-amino-1-phenylpropan-1-ol

> <JCHEM_LOGP>
0.8852543346666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.896164133633945

> <JCHEM_PKA_STRONGEST_BASIC>
9.370138989147625

> <JCHEM_POLAR_SURFACE_AREA>
46.25

> <JCHEM_REFRACTIVITY>
44.9127

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
fenilpropanolamina

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0270570 ((-)-norephedrine)

Download
PDB for NP0270570 ((-)-norephedrine)
HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   6.160   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  N   UNK     0      -1.334   3.850   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

Download
3D PDB for NP0270570 ((-)-norephedrine)
Download
SMILES for NP0270570 ((-)-norephedrine)
C[C@H](N)[C@H](O)C1=CC=CC=C1
Download
INCHI for NP0270570 ((-)-norephedrine)
InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1
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View in JSmol
Synonyms
ValueSource
(-)-NorephedrinChEBI
(1R,2S)-(-)-NorephedrineChEBI
(1R,2S)-2-Amino-1-phenyl-1-propanolChEBI
(1R,2S)-NorephedrineChEBI
(R,S)-(-)-NorephedrineChEBI
Erythro-(1R,2S)-norephedrineChEBI
L-(-)-NorephedrineChEBI
L-NorephedrineChEBI
L-PhenylpropanolamineChEBI
PhenylpropanolamineMeSH
Triaminic DMMeSH
DexatrimMeSH
Hydrochloride, phenylpropanolamineMeSH
ProlamineMeSH
PropagestMeSH
NorephedrineMeSH
Phenylpropanolamine hydrochlorideMeSH
Chemical FormulaC9H13NO
Average Mass151.2090 Da
Monoisotopic Mass151.09971 Da
IUPAC Name(1R,2S)-2-amino-1-phenylpropan-1-ol
Traditional Namefenilpropanolamina
CAS Registry NumberNot Available
SMILES
C[C@H](N)[C@H](O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1
InChI KeyDLNKOYKMWOXYQA-CBAPKCEASA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Catha edulisLOTUS Database
Ephedra distachyaLOTUS Database
Ephedra sinicaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassPhenylpropanes  
Direct ParentPhenylpropanes  
Alternative Parents
Substituents
  • Phenylpropane
    • 

  • Aralkylamine
    • 

  • 1,2-aminoalcohol
    • 

  • Secondary alcohol
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic alcohol
    • 

  • Organopnictogen compound
    • 

  • Primary amine
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Amine
    • 

  • Alcohol
    • 

  • 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
logP0.89ChemAxon
pKa (Strongest Acidic)13.9ChemAxon
pKa (Strongest Basic)9.37ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.91 m³·mol⁻¹ChemAxon
Polarizability16.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00055789  
Chemspider ID9875  
KEGG Compound IDC16719  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10297  
PDB IDNot Available
ChEBI ID80680  
Good Scents IDNot Available
References
General References
  1. Hitchcock SR, Casper DM, Vaughn JF, Finefield JM, Ferrence GM, Esken JM: Intramolecular chiral relay at stereogenic nitrogen. Synthesis and application of a new chiral auxiliary derived from (1R,2S)-norephedrine and acetone. J Org Chem. 2004 Feb 6;69(3):714-8. doi: 10.1021/jo035325n. [PubMed:14750795  ] 
  2. Mathys K, Brenneisen R: Determination of (S)-(-)-cathinone and its metabolites (R,S)-(-)-norephedrine and (R,R)-(-)-norpseudoephedrine in urine by high-performance liquid chromatography with photodiode-array detection. J Chromatogr. 1992 Feb 28;593(1-2):79-85. doi: 10.1016/0021-9673(92)80270-5. [PubMed:1639915  ] 
  3. Krizevski R, Bar E, Shalit O, Sitrit Y, Ben-Shabat S, Lewinsohn E: Composition and stereochemistry of ephedrine alkaloids accumulation in Ephedra sinica Stapf. Phytochemistry. 2010 Jun;71(8-9):895-903. doi: 10.1016/j.phytochem.2010.03.019.  Epub 2010 Apr 24. [PubMed:20417943  ] 
  4. Shinohara J, Kobayashi K, Sato-Akaba H, Itozaki H: Nuclear quadrupole resonance of norephedrine. Solid State Nucl Magn Reson. 2011 Oct;40(3):121-5. doi:  10.1016/j.ssnmr.2011.08.005. Epub 2011 Sep 6. [PubMed:21924876  ] 
  5. Hagel JM, Krizevski R, Kilpatrick K, Sitrit Y, Marsolais F, Lewinsohn E, Facchini PJ: Expressed sequence tag analysis of khat (Catha edulis) provides a putative molecular biochemical basis for the biosynthesis of phenylpropylamino alkaloids. Genet Mol Biol. 2011 Oct;34(4):640-6. doi: 10.1590/S1415-47572011000400017. Epub  2011 Oct 1. [PubMed:22215969  ] 
  6. LOTUS database [Link]