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Showing NP-Card for Isoalliin (NP0045368)

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Record Information
Version2.0
Created at2022-03-17 19:18:44 UTC
Updated at2022-03-17 19:18:44 UTC
NP-MRD IDNP0045368
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsoalliin
DescriptionIsoalliin 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). The process involves two stages: Elimination of 2-propenesulfenic acid from the amino acid unit (with α-aminoacrylic acid as a byproduct), and then condensation of two of the sulfenic acid molecules. Isoalliin is a very strong basic compound (based on its pKa). Outside of the human body, Isoalliin has been detected, but not quantified in, several different foods, such as cloudberries, persian limes, cloud ear fungus, caraway, and japanese walnuts. This could make isoalliin a potential biomarker for the consumption of these foods. Alliinase is responsible for catalyzing chemical reactions that produce the volatile chemicals that give these foods their flavors, odors, and tear-inducing properties. There are a range of similar enzymes that can react with the cysteine-derived sulfoxides present in different species. The PDB accession codes are 1LK9, 2HOR, and 2HOX. The systematic name of this enzyme class is S-alkyl-L-cysteine S-oxide alkyl-sulfenate-lyase (2-aminoacrylate-forming). Isoalliin is found in Allium ampeloprasum. In onions, an isomer of alliin, isoalliin, is converted to 1-propenesulfenic acid.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045368 (Isoalliin)


  Mrv0541 02241214392D          

 11 10  0  0  0  0            999 V2000
    1.6776   -0.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0674   -0.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3810   -0.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911    0.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6776    0.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6776   -0.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6776    0.8386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0674    0.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3810    0.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3047    0.4573    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3047   -0.3047    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  8  1  0  0  0  0
  4  5  2  0  0  0  0
  4 10  1  0  0  0  0
  5  6  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
M  END
Download

3D MOL for NP0045368 (Isoalliin)

     RDKit          3D

 22 21  0  0  0  0  0  0  0  0999 V2000
    2.6242    1.4155   -0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725    0.0602   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4155   -0.9661    0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7868   -0.6296    0.7984 S   0  0  0  0  0  4  0  0  0  0  0  0
    0.3782   -1.5075    1.9623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4450   -0.7504   -0.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855   -0.4388    0.1410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7920    0.8935    0.7061 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8988   -0.6384   -0.8108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405   -1.7347   -1.3903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7854    0.3815   -1.0645 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0953    2.0597   -0.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8062    1.8954    0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5346    1.4732   -0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1936   -0.0561   -0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8206   -1.9907    0.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2627   -0.0304   -1.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4675   -1.7808   -0.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9274   -1.1580    0.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8697    1.1640    1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2250    1.5555    0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3280    0.7831   -0.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  4  3  1  6
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  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
  3 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  1
  8 20  1  0
  8 21  1  0
 11 22  1  0
M  END
Download

3D SDF for NP0045368 (Isoalliin)


  Mrv0541 02241214392D          

 11 10  0  0  0  0            999 V2000
    1.6776   -0.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0674   -0.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3810   -0.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911    0.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6776    0.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6776   -0.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6776    0.8386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0674    0.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3810    0.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3047    0.4573    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3047   -0.3047    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  8  1  0  0  0  0
  4  5  2  0  0  0  0
  4 10  1  0  0  0  0
  5  6  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
M  END
> <DATABASE_ID>
NP0045368

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C/S(=O)CC(N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2-3,5H,4,7H2,1H3,(H,8,9)/b3-2-

> <INCHI_KEY>
OKYHUOHBRKWCQJ-IHWYPQMZSA-N

> <FORMULA>
C6H11NO3S

> <MOLECULAR_WEIGHT>
177.221

> <EXACT_MASS>
177.045963913

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
16.8527998402581

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-[(1Z)-prop-1-ene-1-sulfinyl]propanoic acid

> <ALOGPS_LOGP>
-1.82

> <JCHEM_LOGP>
-3.5050341615732736

> <ALOGPS_LOGS>
-0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8370753162837814

> <JCHEM_PKA_STRONGEST_BASIC>
8.437867218516812

> <JCHEM_POLAR_SURFACE_AREA>
80.38999999999999

> <JCHEM_REFRACTIVITY>
43.96339999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-[(1Z)-prop-1-ene-1-sulfinyl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0045368 (Isoalliin)

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PDB for NP0045368 (Isoalliin)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       3.132  -1.565   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.992  -0.854   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.711  -1.565   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.850   1.565   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.132   0.711   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.132  -0.854   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.132   1.565   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.992   0.711   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.711   1.423   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0      -0.569   0.854   0.000  0.00  0.00           S+0
HETATM   11  O   UNK     0      -0.569  -0.569   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2                                                            
CONECT    4    5   10                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    8                                                            
CONECT    8    2    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    4    9   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0045368 (Isoalliin)
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SMILES for NP0045368 (Isoalliin)
C\C=C/S(=O)CC(N)C(O)=O
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INCHI for NP0045368 (Isoalliin)
InChI=1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2-3,5H,4,7H2,1H3,(H,8,9)/b3-2-
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View in JSmol
Synonyms
ValueSource
3-(1-Propenylsulfinyl)alanine, 9ciHMDB
S-(1-Propenyl)cysteine sulfoxideHMDB
S-[(e)-Prop-1-enyl]-L-cysteine S-oxideHMDB
2-Amino-3-[(1Z)-prop-1-ene-1-sulfinyl]propanoateGenerator
2-Amino-3-[(1Z)-prop-1-ene-1-sulphinyl]propanoateGenerator
2-Amino-3-[(1Z)-prop-1-ene-1-sulphinyl]propanoic acidGenerator
S-(2-Propenyl)cysteine sulfoxideMeSH
IsoalliinMeSH
AlliinMeSH
Alliin, (L-ala)-(R)-isomerMeSH
Alliin, (L-ala)-isomerMeSH
PCSOMeSH
S-Allylcysteine sulfoxideMeSH
Alliin, (L-ala)-(S)-isomerMeSH
Chemical FormulaC6H11NO3S
Average Mass177.2210 Da
Monoisotopic Mass177.04596 Da
IUPAC Name2-amino-3-[(1Z)-prop-1-ene-1-sulfinyl]propanoic acid
Traditional Name2-amino-3-[(1Z)-prop-1-ene-1-sulfinyl]propanoic acid
CAS Registry Number23315-20-0
SMILES
C\C=C/S(=O)CC(N)C(O)=O
InChI Identifier
InChI=1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2-3,5H,4,7H2,1H3,(H,8,9)/b3-2-
InChI KeyOKYHUOHBRKWCQJ-IHWYPQMZSA-N
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
Allium ampeloprasumLOTUS Database
Allium cepaFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Allium fistulosumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Allium sativumFooDB
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
    • 

  • Sulfoxide
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Sulfinyl compound
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Primary amine
    • 

  • Organosulfur compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • 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-1.8ALOGPS
logP-3.5ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)1.84ChemAxon
pKa (Strongest Basic)8.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity43.96 m³·mol⁻¹ChemAxon
Polarizability16.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029441  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000549  
KNApSAcK IDC00001389  
Chemspider IDNot Available
KEGG Compound IDC08295  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlliinase  
METLIN IDNot Available
PubChem Compound6122729  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available