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Showing NP-Card for L-Indospicine (NP0050680)

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Record Information
Version2.0
Created at2022-04-27 22:01:48 UTC
Updated at2022-04-27 22:01:48 UTC
NP-MRD IDNP0050680
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Indospicine
DescriptionL-indospicine belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-indospicine 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. L-Indospicine is found in Indigofera hendecaphylla, Indigofera hirsuta and Indigofera spicata . L-Indospicine was first documented in 1988 (PMID: 3214366). Based on a literature review a small amount of articles have been published on L-indospicine (PMID: 33369767) (PMID: 27338015) (PMID: 11122512) (PMID: 21323657).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050680 (L-Indospicine)


  Mrv1652304282200012D          

 12 11  0  0  1  0            999 V2000
    4.4270    2.5559    0.0000 C   0  0  1  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 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    3.3809    0.0000 N   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
    5.8559    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
    7.2849    2.5559    0.0000 C   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 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  1  5  1  1  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
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3D MOL for NP0050680 (L-Indospicine)

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3D SDF for NP0050680 (L-Indospicine)

  Mrv1652304282200012D          

 12 11  0  0  1  0            999 V2000
    4.4270    2.5559    0.0000 C   0  0  1  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 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    3.3809    0.0000 N   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
    5.8559    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
    7.2849    2.5559    0.0000 C   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 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  1  5  1  1  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050680

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](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)/t5-/m0/s1

> <INCHI_KEY>
SILQDLDAWPQMEL-YFKPBYRVSA-N

> <FORMULA>
C7H15N3O2

> <MOLECULAR_WEIGHT>
173.216

> <EXACT_MASS>
173.116426735

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.307313424967617

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-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>
113.18999999999998

> <JCHEM_REFRACTIVITY>
54.906000000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indospicine

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0050680 (L-Indospicine)
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PDB for NP0050680 (L-Indospicine)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.596   4.771   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.930   2.461   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       8.264   6.311   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      16.266   4.771   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      14.932   2.461   0.000  0.00  0.00           N+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    1                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   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 NP0050680 (L-Indospicine)
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SMILES for NP0050680 (L-Indospicine)
N[C@@H](CCCCC(N)=N)C(O)=O
Download
INCHI for NP0050680 (L-Indospicine)
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)/t5-/m0/s1
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View in JSmol
Synonyms
ValueSource
IndospicineChEBI
Chemical FormulaC7H15N3O2
Average Mass173.2160 Da
Monoisotopic Mass173.11643 Da
IUPAC Name(2S)-2-amino-6-carbamimidoylhexanoic acid
Traditional Nameindospicine
CAS Registry NumberNot Available
SMILES
N[C@@H](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)/t5-/m0/s1
InChI KeySILQDLDAWPQMEL-YFKPBYRVSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Indigofera hendecaphyllaLOTUS Database
Indigofera hirsutaLOTUS Database
Indigofera spicataPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentL-alpha-amino acids  
Alternative Parents
Substituents
  • L-alpha-amino acid
    • 

  • Medium-chain fatty acid
    • 

  • Amino fatty acid
    • 

  • Fatty acid
    • 

  • Fatty acyl
    • 

  • Amino acid
    • 

  • Amidine
    • 

  • Carboxylic acid amidine
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboximidamide
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
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
Polarizability18.31 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 IDC00001373  
Chemspider ID97122  
KEGG Compound IDC08288  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIndospicine  
METLIN IDNot Available
PubChem Compound108010  
PDB IDNot Available
ChEBI ID6253  
Good Scents IDNot Available
References
General References
  1. Darby S, Sanchez LC, Mallicote MF, House AM, Plummer CE, Nadruz V, Benmoha RH, Roberts SM, Derendorf H, Silva-Sanchez C, Claire J, MacKay RJ: Plasma l-indospicine and 3-nitropropionic acid in ponies fed creeping indigo: Comparison with results from an episode of presumptive creeping indigo toxicosis. Equine Vet J. 2022 Jan;54(1):145-152. doi: 10.1111/evj.13415. Epub 2021 Feb 15. [PubMed:33369767  ] 
  2. Lang CS, Wong SH, Chow S, Challinor VL, Yong KW, Fletcher MT, Arthur DM, Ng JC, De Voss JJ: Synthesis of l-indospicine, [5,5,6-(2)H3]-l-indospicine and l-norindospicine. Org Biomol Chem. 2016 Jul 12;14(28):6826-32. doi: 10.1039/c6ob01187j. [PubMed:27338015  ] 
  3. Pollitt S, Hegarty MP, Pass MA: Analysis of the amino acid indospicine in biological samples by high performance liquid chromatography. Nat Toxins. 1999;7(6):233-40. doi:  10.1002/1522-7189(199911/12)7:6<233::aid-nt59>3.0.co;2-3. [PubMed:11122512  ] 
  4. FitzGerald LM, Fletcher MT, Paul AE, Mansfield CS, O'Hara AJ: Hepatotoxicosis in dogs consuming a diet of camel meat contaminated with indospicine. Aust Vet J. 2011 Mar;89(3):95-100. doi: 10.1111/j.1751-0813.2010.00684.x. [PubMed:21323657  ] 
  5. Hegarty MP, Kelly WR, McEwan D, Williams OJ, Cameron R: Hepatotoxicity to dogs of horse meat contaminated with indospicine. Aust Vet J. 1988 Nov;65(11):337-40. doi: 10.1111/j.1751-0813.1988.tb14259.x. [PubMed:3214366  ]