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Showing NP-Card for Putreanine (NP0087453)

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Record Information
Version1.0
Created at2022-05-11 16:50:05 UTC
Updated at2022-05-11 16:50:05 UTC
NP-MRD IDNP0087453
Secondary Accession NumbersNone
Natural Product Identification
Common NamePutreanine
DescriptionPutreanine belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom. Putreanine is a very strong basic compound (based on its pKa). Putreanine is a new amino acid isolated from mammalian and bird brain. Putreanine appears in the brain of rats 2 weeks after birth and subsequently its concentration increases for several months. Its concentration was highest in caudal regions of the brain, and the white matter of the cerebral and cerebellar cortices and the spinal cord contained more than grey matter of the corresponding areas. The concentration of this amino acid in mammalian brain is roughly 50 mmoles per g, which is comparable to the concentrations of branched amino acids, aromatic amino acids, histidine, and ornithine in the same tissue. This amino acid can be synthesized by condensation of 4-phthalimino-1-bromobutane and ethyl b-alaninate followed by add hydrolysis. It was first documented in 1969 (PMID: 5350953). Its structure represents a condensation of putrescine and b-alanine and is therefore named putreanine.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0087453 (Putreanine)


  Mrv0541 02231220332D          

 11 10  0  0  0  0            999 V2000
   10.5911  -20.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4160  -20.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8907  -18.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1786  -20.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8284  -19.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0658  -18.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3031  -18.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3537  -20.9065    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   12.6533  -19.4775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1280  -18.0491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8907  -17.3346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  2  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  7 11  2  0  0  0  0
M  CHG  1   8   1
M  END
Download

3D MOL for NP0087453 (Putreanine)

     RDKit          3D

 28 27  0  0  0  0  0  0  0  0999 V2000
   -2.6618    1.4269    0.7521 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.3436    0.3053    0.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8012   -1.0357    0.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4605   -1.3946    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3163   -0.4872    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9393   -1.0292   -0.1727 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8966    0.0281   -0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2611   -0.3326   -0.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1368    0.8491   -0.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1942    1.5762   -1.5496 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8317    1.1402    0.6209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0543    1.2875    1.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2327    2.0072   -0.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4206    2.1022    1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4459    0.4674   -0.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4097    0.3187    0.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8606   -1.2616    1.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5276   -1.7839    0.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1691   -2.4296    0.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -1.5286   -1.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4972    0.5220    0.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233   -0.4130    1.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2385   -1.8358    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5194    0.9336   -0.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9970    0.3329    1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227   -1.1685    0.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1795   -0.6865   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0597    2.0895    0.9674 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  1 12  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
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
 11 28  1  0
M  CHG  1   1   1
M  END
Download

3D SDF for NP0087453 (Putreanine)


  Mrv0541 02231220332D          

 11 10  0  0  0  0            999 V2000
   10.5911  -20.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4160  -20.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8907  -18.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1786  -20.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8284  -19.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0658  -18.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3031  -18.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3537  -20.9065    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   12.6533  -19.4775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1280  -18.0491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8907  -17.3346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  2  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  7 11  2  0  0  0  0
M  CHG  1   8   1
M  END
> <DATABASE_ID>
NP0087453

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[NH3+]CCCCNCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H16N2O2/c8-4-1-2-5-9-6-3-7(10)11/h9H,1-6,8H2,(H,10,11)/p+1

> <INCHI_KEY>
BTSHXVLJDRJCMM-UHFFFAOYSA-O

> <FORMULA>
C7H17N2O2

> <MOLECULAR_WEIGHT>
161.2221

> <EXACT_MASS>
161.129002798

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.474893165728353

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(4-azaniumylbutyl)amino]propanoic acid

> <ALOGPS_LOGP>
-2.40

> <JCHEM_LOGP>
-3.437169972228818

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.0456176610881665

> <JCHEM_PKA_STRONGEST_BASIC>
10.68879594603231

> <JCHEM_POLAR_SURFACE_AREA>
76.97

> <JCHEM_REFRACTIVITY>
54.23

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(4-ammoniobutyl)amino]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0087453 (Putreanine)

Download
PDB for NP0087453 (Putreanine)
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  C   UNK     0      19.770 -37.692   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.310 -37.692   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.929 -35.025   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.000 -39.025   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.080 -36.358   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.389 -35.025   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.699 -33.692   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      17.460 -39.025   0.000  0.00  0.00           N+1
HETATM    9  N   UNK     0      23.619 -36.358   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      28.239 -33.692   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      25.929 -32.358   0.000  0.00  0.00           O+0
CONECT    1    4    2                                                       
CONECT    2    1    5                                                       
CONECT    3    6    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    3    9                                                       
CONECT    7    3   10   11                                                  
CONECT    8    4                                                            
CONECT    9    5    6                                                       
CONECT   10    7                                                            
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

Download
3D PDB for NP0087453 (Putreanine)
Download
SMILES for NP0087453 (Putreanine)
[NH3+]CCCCNCCC(O)=O
Download
INCHI for NP0087453 (Putreanine)
InChI=1S/C7H16N2O2/c8-4-1-2-5-9-6-3-7(10)11/h9H,1-6,8H2,(H,10,11)/p+1
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View in JSmol
Synonyms
ValueSource
N-(2-Carboxyethyl)putrescineHMDB
N-(4-Aminobutyl)-3-aminopropionic acidHMDB
N-(4-Aminobutyl)-beta-alanineHMDB
3-[(4-Azaniumylbutyl)amino]propanoateHMDB
Chemical FormulaC7H17N2O2
Average Mass161.2221 Da
Monoisotopic Mass161.12900 Da
IUPAC Name3-[(4-azaniumylbutyl)amino]propanoic acid
Traditional Name3-[(4-ammoniobutyl)amino]propanoic acid
CAS Registry NumberNot Available
SMILES
[NH3+]CCCCNCCC(O)=O
InChI Identifier
InChI=1S/C7H16N2O2/c8-4-1-2-5-9-6-3-7(10)11/h9H,1-6,8H2,(H,10,11)/p+1
InChI KeyBTSHXVLJDRJCMM-UHFFFAOYSA-O
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 beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentBeta amino acids and derivatives  
Alternative Parents
Substituents
  • Beta amino acid or derivatives
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Secondary aliphatic amine
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Secondary amine
    • 

  • Amine
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxide
    • 

  • Primary aliphatic amine
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic cation
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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-2.4ALOGPS
logP-3.4ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4.05ChemAxon
pKa (Strongest Basic)10.69ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area76.97 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity54.23 m³·mol⁻¹ChemAxon
Polarizability18.47 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0006078  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023827  
KNApSAcK IDNot Available
Chemspider ID21232259  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477800  
PDB IDNot Available
ChEBI ID89478  
Good Scents IDNot Available
References
General References
  1. Kakimoto Y, Nakajima T, Kumon A, Matsuoka Y, Imaoka N, Sano I: Putreanine, N-(4-aminobutyl)-3-aminopropionic acid. An amino acid occurring uniquely in the mammalian central nervous system. J Biol Chem. 1969 Nov 10;244(21):6003-7. [PubMed:5350953  ]