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Showing NP-Card for Kynuramine (NP0091996)

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Record Information
Version2.0
Created at2022-05-11 18:54:16 UTC
Updated at2022-05-11 18:54:16 UTC
NP-MRD IDNP0091996
Secondary Accession NumbersNone
Natural Product Identification
Common NameKynuramine
DescriptionKynuramine belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. An aromatic ketone that is aniline substituted at position 2 by a 3-aminopropanoyl group. Kynuramine was first documented in 1977 (PMID: 562342). Kynuramine is a very strong basic compound (based on its pKa) (PMID: 22547660) (PMID: 3428356) (PMID: 4017223) (PMID: 510362) (PMID: 6115758) (PMID: 6132830).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0091996 (Kynuramine)


  Mrv0541 02241203522D          

 12 12  0  0  0  0            999 V2000
   10.9325   -5.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1076   -5.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3449   -6.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6950   -6.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9325   -8.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3449   -9.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9325   -6.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1076   -6.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3449   -7.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9325   -9.8182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6950   -7.6754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1699   -7.6754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  2  1  0  0  0  0
  2  4  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  7  8  2  0  0  0  0
  8 11  1  0  0  0  0
  9 12  2  0  0  0  0
M  END
Download

3D MOL for NP0091996 (Kynuramine)

     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.9905   -0.5289   -1.5582 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6624    0.4380   -0.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9606   -0.0815    0.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6844   -0.7438    0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6859   -1.9484   -0.0185 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5700   -0.0168    0.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6539    1.3088    0.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8451    1.9833    0.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9947    1.2860    0.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9398   -0.0429    0.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446   -0.7197    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7078   -2.0993   -0.2908 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6185   -1.2790   -1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6097   -0.4693   -2.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9676    1.1897   -1.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5597    1.0261   -0.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8491    0.6998    1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7007   -0.8039    1.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2489    1.8483    0.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8967    3.0501    1.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9509    1.7772    0.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8483   -0.6139   -0.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7308   -2.8674    0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6555   -2.3924   -1.2947 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  2  0
  4  6  1  0
  6 11  2  0
 11 12  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
 12 23  1  0
 12 24  1  0
 10 22  1  0
  9 21  1  0
  8 20  1  0
  7 19  1  0
M  END
Download

3D SDF for NP0091996 (Kynuramine)


  Mrv0541 02241203522D          

 12 12  0  0  0  0            999 V2000
   10.9325   -5.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1076   -5.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3449   -6.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6950   -6.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9325   -8.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3449   -9.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9325   -6.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1076   -6.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3449   -7.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9325   -9.8182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6950   -7.6754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1699   -7.6754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  2  1  0  0  0  0
  2  4  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  7  8  2  0  0  0  0
  8 11  1  0  0  0  0
  9 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0091996

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCC(=O)C1=C(N)C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H12N2O/c10-6-5-9(12)7-3-1-2-4-8(7)11/h1-4H,5-6,10-11H2

> <INCHI_KEY>
QLPVTIQQFGWSQQ-UHFFFAOYSA-N

> <FORMULA>
C9H12N2O

> <MOLECULAR_WEIGHT>
164.2044

> <EXACT_MASS>
164.094963016

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
17.76518950711435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-amino-1-(2-aminophenyl)propan-1-one

> <ALOGPS_LOGP>
-0.00

> <JCHEM_LOGP>
0.6648502743333332

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.943583174391765

> <JCHEM_PKA_STRONGEST_BASIC>
9.505652963303666

> <JCHEM_POLAR_SURFACE_AREA>
69.11

> <JCHEM_REFRACTIVITY>
49.2203

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-amino-1-(2-aminophenyl)propan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0091996 (Kynuramine)

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PDB for NP0091996 (Kynuramine)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      20.407 -10.326   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.867 -10.326   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.177 -11.660   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.097 -11.660   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.407 -15.660   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.177 -16.994   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.407 -12.994   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.867 -12.994   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.177 -14.327   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      20.407 -18.327   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      18.097 -14.327   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      22.717 -14.327   0.000  0.00  0.00           O+0
CONECT    1    3    2                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    3    9    8                                                  
CONECT    8    4    7   11                                                  
CONECT    9    5    7   12                                                  
CONECT   10    6                                                            
CONECT   11    8                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0091996 (Kynuramine)
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SMILES for NP0091996 (Kynuramine)
NCCC(=O)C1=C(N)C=CC=C1
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INCHI for NP0091996 (Kynuramine)
InChI=1S/C9H12N2O/c10-6-5-9(12)7-3-1-2-4-8(7)11/h1-4H,5-6,10-11H2
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View in JSmol
Synonyms
ValueSource
DiaminopropiophenoneChEBI
3-Amino-1-(2-aminophenyl)-1-propanoneHMDB
2,3 DiaminopropiophenoneHMDB
2,3-DiaminopropiophenoneHMDB
Chemical FormulaC9H12N2O
Average Mass164.2044 Da
Monoisotopic Mass164.09496 Da
IUPAC Name3-amino-1-(2-aminophenyl)propan-1-one
Traditional Name3-amino-1-(2-aminophenyl)propan-1-one
CAS Registry NumberNot Available
SMILES
NCCC(=O)C1=C(N)C=CC=C1
InChI Identifier
InChI=1S/C9H12N2O/c10-6-5-9(12)7-3-1-2-4-8(7)11/h1-4H,5-6,10-11H2
InChI KeyQLPVTIQQFGWSQQ-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
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAlkyl-phenylketones  
Alternative Parents
Substituents
  • Alkyl-phenylketone
    • 

  • Benzoyl
    • 

  • Aryl alkyl ketone
    • 

  • Aniline or substituted anilines
    • 

  • Monocyclic benzene moiety
    • 

  • Beta-aminoketone
    • 

  • Benzenoid
    • 

  • Vinylogous amide
    • 

  • Organopnictogen compound
    • 

  • Amine
    • 

  • Primary amine
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic nitrogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP0ALOGPS
logP0.66ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)15.94ChemAxon
pKa (Strongest Basic)9.51ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.11 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.22 m³·mol⁻¹ChemAxon
Polarizability17.77 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012246  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028888  
KNApSAcK IDNot Available
Chemspider ID9311  
KEGG Compound IDNot Available
BioCyc IDCPD-7654  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9692  
PDB IDNot Available
ChEBI ID73472  
Good Scents IDNot Available
References
General References
  1. Li B, Lv X, Geng L, Qing H, Deng Y: Proteoliposome-based capillary electrophoresis for screening membrane protein inhibitors. J Chromatogr Sci. 2012 Aug;50(7):569-73. doi: 10.1093/chromsci/bms053. Epub 2012  Apr 29. [PubMed:22547660  ] 
  2. Mendelson SD, Lee N, Gorzalka BB: Intraventricular administration of l-kynurenine and kynuramine facilitates lordosis in the female rat. Eur J Pharmacol. 1987 Oct 27;142(3):447-51. doi: 10.1016/0014-2999(87)90086-0. [PubMed:3428356  ] 
  3. Matsumoto T, Suzuki O, Furuta T, Asai M, Kurokawa Y, Nimura Y, Katsumata Y, Takahashi I: A sensitive fluorometric assay for serum monoamine oxidase with kynuramine as substrate. Clin Biochem. 1985 Apr;18(2):126-9. doi: 10.1016/s0009-9120(85)80094-1. [PubMed:4017223  ] 
  4. Dial EJ, Clarke DE: Rat and human cardiac monoamine oxidase: a comparison with other tissues. Eur J Pharmacol. 1979 Oct 1;58(3):313-9. doi: 10.1016/0014-2999(79)90480-1. [PubMed:510362  ] 
  5. Massey JB, Churchich JE: Kynuramine, a fluorescent substrate and probe of plasma amine oxidase. J Biol Chem. 1977 Nov 25;252(22):8081-4. [PubMed:562342  ] 
  6. Johnson TD, Clarke DE: An alpha-adrenoceptor inhibitory action of kynuramine. Eur J Pharmacol. 1981 Jul 10;72(4):351-6. doi: 10.1016/0014-2999(81)90574-4. [PubMed:6115758  ] 
  7. Johnson TD, Clarke DE: Blood pressure and heart rate effects of kynuramine in pithed rats. Eur J Pharmacol. 1983 Feb 18;87(2-3):323-6. doi: 10.1016/0014-2999(83)90346-1. [PubMed:6132830  ] 
  8. Charlton KG, Johnson TD, Hamed AT, Clarke DE: Cardiovascular actions of kynuramine and 5-hydroxykynuramine in pithed rats. J Neural Transm. 1983;57(4):199-211. doi: 10.1007/BF01248993. [PubMed:6140297  ] 
  9. Johnson TD, Charlton KG, Clarke DE: Cardiac norepinephrine releasing action of kynuramine, an endogenous diamine derived from L-tryptophan. Life Sci. 1984 Dec 3;35(23):2303-10. doi: 10.1016/0024-3205(84)90521-6. [PubMed:6503615  ] 
  10. Charlton KG, Johnson TD, Maurice RW, Clarke DE: Kynuramine: high affinity for [3H]tryptamine binding sites. Eur J Pharmacol. 1984 Nov 27;106(3):661-4. doi: 10.1016/0014-2999(84)90076-1. [PubMed:6519183  ]