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Showing NP-Card for 3-amino-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid (NP0226005)

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Record Information
Version2.0
Created at2022-09-06 04:54:42 UTC
Updated at2022-09-06 04:54:42 UTC
NP-MRD IDNP0226005
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-amino-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid
DescriptionCarcinine, also known as b-alanylhistamine, belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms. Carcinine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 3-amino-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid is found in Drosophila melanogaster. 3-amino-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid was first documented in 2019 (PMID: 30792494). Based on a literature review a small amount of articles have been published on Carcinine (PMID: 35716886) (PMID: 35435595) (PMID: 32143488) (PMID: 30693765).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0226005 (3-amino-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)


  Mrv1652309062206542D          

 13 13  0  0  0  0            999 V2000
    1.2822    5.6518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    4.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    4.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  4  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
M  END
Download

3D MOL for NP0226005 (3-amino-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)

     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
   -4.0046    0.8480   -0.2307 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0868   -0.5869   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8004   -1.0797   -0.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6121   -0.7179   -0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4675   -1.1638    1.1125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7111    0.0146   -0.6967 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4913    0.4622   -0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6577   -0.0563   -0.9284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9633    0.3620   -0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6760    1.5091   -0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8113    1.4570    0.1163 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8133    0.3275    0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6841   -0.3206    0.5318 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1911    1.2618   -0.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1151    1.1678    0.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9088   -0.8958   -1.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2816   -1.0948    0.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8406   -2.1993   -1.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7419   -0.6775   -2.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8681   -0.6562    1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5333    1.5754   -0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6031    0.2073    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4854    0.3596   -1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5833   -1.1571   -0.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3655    2.2737   -1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5806    0.0209    1.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3817   -1.2412    0.9263 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  9  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
 10 25  1  0
 12 26  1  0
 13 27  1  0
M  END
Download

3D SDF for NP0226005 (3-amino-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)


  Mrv1652309062206542D          

 13 13  0  0  0  0            999 V2000
    1.2822    5.6518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    4.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    4.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  4  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226005

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCC(O)=NCCC1=CN=CN1

> <INCHI_IDENTIFIER>
InChI=1S/C8H14N4O/c9-3-1-8(13)11-4-2-7-5-10-6-12-7/h5-6H,1-4,9H2,(H,10,12)(H,11,13)

> <INCHI_KEY>
ANRUJJLGVODXIK-UHFFFAOYSA-N

> <FORMULA>
C8H14N4O

> <MOLECULAR_WEIGHT>
182.227

> <EXACT_MASS>
182.116761087

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.744500077404755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-amino-N-[2-(1H-imidazol-5-yl)ethyl]propanimidic acid

> <JCHEM_LOGP>
-3.3676402238171024

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
12.957265062729235

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.938829818321956

> <JCHEM_PKA_STRONGEST_BASIC>
10.303908113374586

> <JCHEM_POLAR_SURFACE_AREA>
87.28999999999999

> <JCHEM_REFRACTIVITY>
50.253699999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-amino-N-[2-(3H-imidazol-4-yl)ethyl]propanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0226005 (3-amino-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)

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PDB for NP0226005 (3-amino-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)
HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  N   UNK     0       2.393  10.550   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.393   9.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   8.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   6.700   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.393   5.930   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      -0.274   5.930   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0226005 (3-amino-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)
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SMILES for NP0226005 (3-amino-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)
NCCC(O)=NCCC1=CN=CN1
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INCHI for NP0226005 (3-amino-n-[2-(3h-imidazol-4-yl)ethyl]propanimidic acid)
InChI=1S/C8H14N4O/c9-3-1-8(13)11-4-2-7-5-10-6-12-7/h5-6H,1-4,9H2,(H,10,12)(H,11,13)
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View in JSmol
Synonyms
ValueSource
beta-AlaninylhistamineChEBI
beta-Alanyl-histamineChEBI
beta-AlanylhistamineChEBI
b-AlaninylhistamineGenerator
Β-alaninylhistamineGenerator
b-Alanyl-histamineGenerator
Β-alanyl-histamineGenerator
b-AlanylhistamineGenerator
Β-alanylhistamineGenerator
Chemical FormulaC8H14N4O
Average Mass182.2270 Da
Monoisotopic Mass182.11676 Da
IUPAC Name3-amino-N-[2-(1H-imidazol-5-yl)ethyl]propanimidic acid
Traditional Name3-amino-N-[2-(3H-imidazol-4-yl)ethyl]propanimidic acid
CAS Registry NumberNot Available
SMILES
NCCC(O)=NCCC1=CN=CN1
InChI Identifier
InChI=1S/C8H14N4O/c9-3-1-8(13)11-4-2-7-5-10-6-12-7/h5-6H,1-4,9H2,(H,10,12)(H,11,13)
InChI KeyANRUJJLGVODXIK-UHFFFAOYSA-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
Drosophila melanogasterLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassAzoles  
Sub ClassImidazoles  
Direct ParentImidazoles  
Alternative Parents
Substituents
  • Imidazole
    • 

  • Heteroaromatic compound
    • 

  • Azacycle
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Carboximidic acid derivative
    • 

  • Carboximidic acid
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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-3.4ChemAxon
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)10.3ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area87.29 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity50.25 m³·mol⁻¹ChemAxon
Polarizability19.74 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0249666  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2476  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2574  
PDB IDNot Available
ChEBI ID131429  
Good Scents IDNot Available
References
General References
  1. Zhao M, Song X, Liu W, Qi F, Zhao T, Xia K, Liu Z, Zheng Y: Whole-cell biotransformation for large scale production of carcinine in Escherichia coli. J Biotechnol. 2022 Aug 10;354:45-52. doi: 10.1016/j.jbiotec.2022.06.003. Epub  2022 Jun 16. [PubMed:35716886  ] 
  2. Palmieri B, Vadala M, Urso SU, Baldini LO, Fanelli C, Morales-Medina JC, Iannitti T: A nutraceutical formulation combined with sclerofoam-assisted laser treatment ameliorates chronic venous insufficiency. Lasers Med Sci. 2022 Sep;37(7):2831-2835. doi: 10.1007/s10103-022-03549-5. Epub  2022 Apr 18. [PubMed:35435595  ] 
  3. Vistoli G, Aldini G, Fumagalli L, Dallanoce C, Angeli A, Supuran CT: Activation Effects of Carnosine- and Histidine-Containing Dipeptides on Human Carbonic Anhydrases: A Comprehensive Study. Int J Mol Sci. 2020 Mar 4;21(5):1761. doi: 10.3390/ijms21051761. [PubMed:32143488  ] 
  4. Stenesen D, Moehlman AT, Schellinger JN, Rodan AR, Kramer H: The glial sodium-potassium-2-chloride cotransporter is required for synaptic transmission in the Drosophila visual system. Sci Rep. 2019 Feb 21;9(1):2475. doi: 10.1038/s41598-019-38850-x. [PubMed:30792494  ] 
  5. Carroll L, Karton A, Radom L, Davies MJ, Pattison DI: Carnosine and Carcinine Derivatives Rapidly React with Hypochlorous Acid to Form Chloramines and Dichloramines. Chem Res Toxicol. 2019 Mar 18;32(3):513-525. doi: 10.1021/acs.chemrestox.8b00363.  Epub 2019 Feb 15. [PubMed:30693765  ] 
  6. LOTUS database [Link]