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Showing NP-Card for hypoglycine a (NP0287331)

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Record Information
Version2.0
Created at2022-09-09 16:21:05 UTC
Updated at2022-09-09 16:21:05 UTC
NP-MRD IDNP0287331
Secondary Accession NumbersNone
Natural Product Identification
Common Namehypoglycine a
DescriptionL-Hypoglycin A 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). L-Hypoglycin A is a very strong basic compound (based on its pKa). Outside of the human body, L-Hypoglycin A has been detected, but not quantified in, several different foods, such as banana, wild carrots, boysenberries, sourdocks, and macadamia nut (m. Tetraphylla). hypoglycine a is found in Blighia sapida and Dimocarpus longan. This could make L-hypoglycin a a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0287331 (hypoglycine a)


  Mrv0541 05061304462D          

 10 10  0  0  0  0            999 V2000
    0.2382    1.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8888   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  0  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
   -0.8888   -1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -1.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743   -1.4757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -2.3007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3178   -1.0632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  4  2  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  7  1  0  0  0  0
M  END
Download

3D MOL for NP0287331 (hypoglycine a)

     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
    2.4407    0.7762   -1.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6823   -0.1377   -1.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0483   -1.4812   -1.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8444   -0.7192   -0.2910 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5265   -0.1588   -0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6249    0.6053    1.2413 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3187   -0.2364    2.3774 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9967    1.1513    1.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4414    1.9138    0.4795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7420    0.8180    2.4836 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6976    1.7237   -1.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8615    0.6571   -2.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6815   -2.3776   -1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2192   -1.4941   -2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4426   -0.9492    0.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7955    0.5341   -0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2492   -1.0127   -0.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1194    1.4325    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7752   -1.1559    2.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7865    0.2050    3.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7811   -0.0943    2.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  6  8  1  0
  8 10  1  0
  8  9  2  0
  2  4  1  0
  7 19  1  0
  7 20  1  0
  6 18  1  6
  5 16  1  0
  5 17  1  0
  4 15  1  1
  3 13  1  0
  3 14  1  0
  1 11  1  0
  1 12  1  0
 10 21  1  0
M  END
Download

3D SDF for NP0287331 (hypoglycine a)


  Mrv0541 05061304462D          

 10 10  0  0  0  0            999 V2000
    0.2382    1.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8888   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  0  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
   -0.8888   -1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -1.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743   -1.4757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -2.3007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3178   -1.0632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  4  2  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0287331

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC1CC1=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H11NO2/c1-4-2-5(4)3-6(8)7(9)10/h5-6H,1-3,8H2,(H,9,10)

> <INCHI_KEY>
OOJZCXFXPZGUBJ-UHFFFAOYSA-N

> <FORMULA>
C7H11NO2

> <MOLECULAR_WEIGHT>
141.1677

> <EXACT_MASS>
141.078978601

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
14.815663496141738

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-(2-methylidenecyclopropyl)propanoic acid

> <ALOGPS_LOGP>
-2.23

> <JCHEM_LOGP>
-2.1110315690711

> <ALOGPS_LOGS>
-0.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5154022786939834

> <JCHEM_PKA_STRONGEST_BASIC>
9.508615782922254

> <JCHEM_POLAR_SURFACE_AREA>
63.32000000000001

> <JCHEM_REFRACTIVITY>
36.6948

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hypoglycine A

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0287331 (hypoglycine a)

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PDB for NP0287331 (hypoglycine a)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.445   3.199   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.215   0.325   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.659  -0.445   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.445   1.659   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.325   0.325   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.659  -1.985   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.993  -2.755   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.325  -2.755   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      -2.993  -4.295   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -4.327  -1.985   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    4    5                                                       
CONECT    3    5    6                                                       
CONECT    4    1    2    5                                                  
CONECT    5    2    3    4                                                  
CONECT    6    3    7    8                                                  
CONECT    7    6    9   10                                                  
CONECT    8    6                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0287331 (hypoglycine a)
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SMILES for NP0287331 (hypoglycine a)
NC(CC1CC1=C)C(O)=O
Download
INCHI for NP0287331 (hypoglycine a)
InChI=1S/C7H11NO2/c1-4-2-5(4)3-6(8)7(9)10/h5-6H,1-3,8H2,(H,9,10)
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View in JSmol
Synonyms
ValueSource
2-Amino-3-(2-methylenecyclopropyl)propionic acidChEBI
2-Amino-3-(2-methylenecyclopropyl)propionateGenerator
2-Amino-4,5-methylenehex-5-enoic acidHMDB
2-MethylenecyclopropanealanineHMDB
2-MethylenecyclopropanylalanineHMDB
2-MethyleneL-cyclopropanealanineHMDB
alpha-Amino-2-methylenecyclopropanepropanoic acidHMDB
alpha-Amino-2-methylenecyclopropanepropionic acidHMDB
alpha-Amino-beta-(2-methylenecyclopropyl)propionic acidHMDB
alpha-Aminomethylenecyclopropanepropionic acidHMDB
beta-(Methylenecyclopropyl)alanineHMDB
Hypoglycin aHMDB
Hypoglycine aHMDB
L-alpha-Amino-beta-methylenecyclopropanepropionic acidHMDB
L-HypoglycinHMDB
Hypoglycin, (S)-isomerHMDB
HypoglycinHMDB
Hypoglycin, carboxy-(14)C-labeledHMDB
2-Amino-3-(2-methylenecyclopropyl)propanoateGenerator
Chemical FormulaC7H11NO2
Average Mass141.1677 Da
Monoisotopic Mass141.07898 Da
IUPAC Name2-amino-3-(2-methylidenecyclopropyl)propanoic acid
Traditional Namehypoglycine A
CAS Registry NumberNot Available
SMILES
NC(CC1CC1=C)C(O)=O
InChI Identifier
InChI=1S/C7H11NO2/c1-4-2-5(4)3-6(8)7(9)10/h5-6H,1-3,8H2,(H,9,10)
InChI KeyOOJZCXFXPZGUBJ-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
Blighia sapidaLOTUS Database
Dimocarpus longanLOTUS 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
    • 

  • Carbocyclic fatty acid
    • 

  • Fatty acyl
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxide
    • 

  • Primary aliphatic amine
    • 

  • Organopnictogen compound
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Amine
    • 

  • 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-2.2ALOGPS
logP-2.1ChemAxon
logS-0.15ALOGPS
pKa (Strongest Acidic)2.52ChemAxon
pKa (Strongest Basic)9.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity36.69 m³·mol⁻¹ChemAxon
Polarizability14.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029427  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000529  
KNApSAcK IDC00001372  
Chemspider ID8728  
KEGG Compound IDC08287  
BioCyc IDCPD-9699  
BiGG IDNot Available
Wikipedia LinkHypoglycin A  
METLIN IDNot Available
PubChem Compound9081  
PDB IDNot Available
ChEBI ID136270  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]