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Showing NP-Card for 6-amidino-2-aminohexanoic acid (NP0301456)

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Record Information
Version2.0
Created at2022-09-10 14:25:45 UTC
Updated at2022-09-10 14:25:45 UTC
NP-MRD IDNP0301456
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-amidino-2-aminohexanoic acid
Description24185-98-6, Also known as indospicine, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 6-amidino-2-aminohexanoic acid is found in Indigofera spicata. 24185-98-6 Is a very strong basic compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0301456 (6-amidino-2-aminohexanoic acid)


  Mrv1533004171516072D          

 12 11  0  0  0  0            999 V2000
    7.2849    3.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0301456 (6-amidino-2-aminohexanoic acid)

     RDKit          3D

 27 26  0  0  0  0  0  0  0  0999 V2000
    3.1582    1.2912   -2.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7608    0.9873   -1.3514 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2679    0.1753   -0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0723   -0.2467    0.5889 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8852   -0.3333   -0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1449    0.0828    0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2911   -0.3704    0.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1116    0.1446   -0.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5274   -0.3532   -0.3868 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2993    0.1856   -1.5219 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2471   -0.0575    0.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3079    0.6156    0.7939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8561   -0.4668    2.1033 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1376   -1.2689    0.8492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6362    0.4000    1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4320    0.0560   -1.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9021   -1.4471   -0.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1521    1.1801    0.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6511   -0.4048    1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6871    0.1119    1.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133   -1.4624    0.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1780    1.2713   -0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7318   -0.1152   -1.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5161   -1.4741   -0.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6214    1.1246   -1.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6361    0.2467   -2.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7760    0.1275    2.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  9 11  1  0
 11 13  1  0
 11 12  2  0
 10 25  1  0
 10 26  1  0
  9 24  1  6
  8 22  1  0
  8 23  1  0
  7 20  1  0
  7 21  1  0
  6 18  1  0
  6 19  1  0
  5 16  1  0
  5 17  1  0
  4 14  1  0
  4 15  1  0
  2  1  1  0
 13 27  1  0
M  END
Download

3D SDF for NP0301456 (6-amidino-2-aminohexanoic acid)


  Mrv1533004171516072D          

 12 11  0  0  0  0            999 V2000
    7.2849    3.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0301456

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CCCCC(N)=N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H15N3O2/c8-5(7(11)12)3-1-2-4-6(9)10/h5H,1-4,8H2,(H3,9,10)(H,11,12)

> <INCHI_KEY>
SILQDLDAWPQMEL-UHFFFAOYSA-N

> <FORMULA>
C7H15N3O2

> <MOLECULAR_WEIGHT>
173.216

> <EXACT_MASS>
173.116426735

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.55543963408572

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6-carbamimidoylhexanoic acid

> <ALOGPS_LOGP>
-3.53

> <JCHEM_LOGP>
-2.4446660522630244

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.531897814827828

> <JCHEM_PKA_STRONGEST_BASIC>
12.880917670357626

> <JCHEM_POLAR_SURFACE_AREA>
113.19000000000001

> <JCHEM_REFRACTIVITY>
54.906

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-amidino-2-aminohexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0301456 (6-amidino-2-aminohexanoic acid)

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PDB for NP0301456 (6-amidino-2-aminohexanoic acid)
HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  N   UNK     0      13.598   6.311   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       5.596   4.771   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       6.930   2.461   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0301456 (6-amidino-2-aminohexanoic acid)
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SMILES for NP0301456 (6-amidino-2-aminohexanoic acid)
NC(CCCCC(N)=N)C(O)=O
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INCHI for NP0301456 (6-amidino-2-aminohexanoic acid)
InChI=1S/C7H15N3O2/c8-5(7(11)12)3-1-2-4-6(9)10/h5H,1-4,8H2,(H3,9,10)(H,11,12)
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View in JSmol
Synonyms
ValueSource
Indospicine, (+-)-isomerMeSH
IndospicineMeSH
6-Amidino-2-aminohexanoic acidMeSH
L-IndospicineChEMBL
2-amino-6-CarbamimidoylhexanoateGenerator
Chemical FormulaC7H15N3O2
Average Mass173.2160 Da
Monoisotopic Mass173.11643 Da
IUPAC Name2-amino-6-carbamimidoylhexanoic acid
Traditional Name6-amidino-2-aminohexanoic acid
CAS Registry NumberNot Available
SMILES
NC(CCCCC(N)=N)C(O)=O
InChI Identifier
InChI=1S/C7H15N3O2/c8-5(7(11)12)3-1-2-4-6(9)10/h5H,1-4,8H2,(H3,9,10)(H,11,12)
InChI KeySILQDLDAWPQMEL-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
Indigofera spicataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlpha amino acids  
Alternative Parents
Substituents
  • Alpha-amino acid
    • 

  • Medium-chain fatty acid
    • 

  • Amino fatty acid
    • 

  • Fatty acyl
    • 

  • Fatty acid
    • 

  • Amino acid
    • 

  • Amidine
    • 

  • Carboxylic acid amidine
    • 

  • Carboxylic acid
    • 

  • Carboximidamide
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Primary amine
    • 

  • Primary aliphatic amine
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organopnictogen compound
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • 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-3.5ALOGPS
logP-2.4ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.53ChemAxon
pKa (Strongest Basic)12.88ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area113.19 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity54.91 m³·mol⁻¹ChemAxon
Polarizability18.56 ųChemAxon
Number of Rings0ChemAxon
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4479245  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]