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Showing NP-Card for (1s,2s)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid (NP0246952)

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Record Information
Version2.0
Created at2022-09-07 08:35:20 UTC
Updated at2022-09-07 08:35:20 UTC
NP-MRD IDNP0246952
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,2s)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid
DescriptionCarnosadine belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. (1s,2s)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid is found in Grateloupia carnosa. (1s,2s)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid was first documented in 2020 (PMID: 32378891). Based on a literature review very few articles have been published on Carnosadine (PMID: 33974420).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0246952 ((1s,2s)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid)


  Mrv1652309072210352D          

 12 12  0  0  1  0            999 V2000
    2.0796   -2.3007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796   -1.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7941   -1.0632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -1.0632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2350    1.5646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7114    1.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627    2.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5332    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  1  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0246952 ((1s,2s)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid)

     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
    3.3088    2.4662    0.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7396    1.5755    0.0912 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0464    0.4959    0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6853   -0.6934   -0.3971 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6890    0.5532    0.4428 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6400    0.5939   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7093    0.6516    0.1192 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0061   -0.5220    1.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8083   -0.2580   -0.2744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6105   -1.1967   -1.3441 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000    0.1246   -0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5380    0.9352    0.9006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2110   -0.4287   -0.7735 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4227   -1.1233    0.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4434   -1.1400   -1.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837    0.5646    1.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7565   -0.3203   -1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8056    1.4716   -1.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9881    1.6703    0.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3811   -1.4118    0.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4551   -0.2521    1.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5170   -1.5588   -1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9874   -0.8551   -2.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6090   -1.3426   -0.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  2  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  1
 11 13  1  0
 11 12  2  0
  9  7  1  0
  4 14  1  0
  4 15  1  0
  2  1  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  1
  8 20  1  0
  8 21  1  0
 10 22  1  0
 10 23  1  0
 13 24  1  0
M  END
Download

3D SDF for NP0246952 ((1s,2s)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid)


  Mrv1652309072210352D          

 12 12  0  0  1  0            999 V2000
    2.0796   -2.3007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796   -1.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7941   -1.0632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -1.0632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2350    1.5646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7114    1.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627    2.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5332    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  1  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0246952

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=N)NC[C@@H]1C[C@@]1(N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H12N4O2/c7-5(8)10-2-3-1-6(3,9)4(11)12/h3H,1-2,9H2,(H,11,12)(H4,7,8,10)/t3-,6-/m0/s1

> <INCHI_KEY>
UKJXPTCZTCDPQL-DZSWIPIPSA-N

> <FORMULA>
C6H12N4O2

> <MOLECULAR_WEIGHT>
172.188

> <EXACT_MASS>
172.096025642

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.86015900478256

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid

> <JCHEM_LOGP>
-3.578667820087002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1476996547210194

> <JCHEM_PKA_STRONGEST_BASIC>
12.531192923616652

> <JCHEM_POLAR_SURFACE_AREA>
125.22000000000001

> <JCHEM_REFRACTIVITY>
51.928000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0246952 ((1s,2s)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid)

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PDB for NP0246952 ((1s,2s)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid)
HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  N   UNK     0       3.882  -4.295   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.882  -2.755   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       5.216  -1.985   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       2.548  -1.985   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.548  -0.445   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.215   0.325   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.325   0.325   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.445   1.659   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.439   2.921   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.328   2.921   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.677   4.316   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.862   2.786   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    8                                                       
CONECT    8    7    6    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0246952 ((1s,2s)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid)
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SMILES for NP0246952 ((1s,2s)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid)
NC(=N)NC[C@@H]1C[C@@]1(N)C(O)=O
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INCHI for NP0246952 ((1s,2s)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid)
InChI=1S/C6H12N4O2/c7-5(8)10-2-3-1-6(3,9)4(11)12/h3H,1-2,9H2,(H,11,12)(H4,7,8,10)/t3-,6-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC6H12N4O2
Average Mass172.1880 Da
Monoisotopic Mass172.09603 Da
IUPAC Name(1S,2S)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid
Traditional Name(1S,2S)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid
CAS Registry NumberNot Available
SMILES
NC(=N)NC[C@@H]1C[C@@]1(N)C(O)=O
InChI Identifier
InChI=1S/C6H12N4O2/c7-5(8)10-2-3-1-6(3,9)4(11)12/h3H,1-2,9H2,(H,11,12)(H4,7,8,10)/t3-,6-/m0/s1
InChI KeyUKJXPTCZTCDPQL-DZSWIPIPSA-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
Grateloupia carnosaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentD-alpha-amino acids  
Alternative Parents
Substituents
  • D-alpha-amino acid
    • 

  • 1-aminocyclopropane-1-carboxylic acid or derivatives
    • 

  • Cyclopropanecarboxylic acid
    • 

  • Cyclopropanecarboxylic acid or derivatives
    • 

  • Amino acid
    • 

  • Guanidine
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboximidamide
    • 

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

  • Organic 1,3-dipolar compound
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary aliphatic amine
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Primary amine
    • 

  • Amine
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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-3.6ChemAxon
pKa (Strongest Acidic)2.15ChemAxon
pKa (Strongest Basic)12.53ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area125.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.93 m³·mol⁻¹ChemAxon
Polarizability16.86 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 IDNot Available
Chemspider ID9194508  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11019326  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Matsui K, Kan Y, Kikuchi J, Matsushima K, Takemura M, Maki H, Kozono I, Ueda T, Minagawa K: Stalobacin: Discovery of Novel Lipopeptide Antibiotics with Potent Antibacterial Activity against Multidrug-Resistant Bacteria. J Med Chem. 2020 Jun 11;63(11):6090-6095. doi: 10.1021/acs.jmedchem.0c00295. Epub 2020 May 19. [PubMed:32378891  ] 
  2. Ohsawa K, Kubota J, Ochiai S, Doi T: Stereoselective Synthesis of 1-Aminocyclopropanecarboxylic Acid Carnosadines via Inter-intramolecular Double Alkylation with Optically Active 2-Methylaziridine Derivatives. J Org Chem. 2021 May 21;86(10):7304-7313. doi: 10.1021/acs.joc.1c00680. Epub 2021  May 11. [PubMed:33974420  ] 
  3. LOTUS database [Link]