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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:21 UTC

Update Date

2022-03-07 02:52:09 UTC

HMDB ID

HMDB0029428

Secondary Accession Numbers

HMDB29428

Metabolite Identification

Common Name

Hypoglycin B

Description

Hypoglycin B is found in fruits. Hypoglycin B is a biologically active component of Blighia sapida (akee apple) Hypoglycin B is a naturally occurring organic compound in the species Blighia sapida. It is particularly concentrated in the fruit of the plant especially in the seeds. Hypoglycin B is toxic if ingested and is a causative agent of Jamaican Vomiting Sickness. It is an amino acid and chemically related to lysine

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0029428
     RDKit          3D
Hypoglycin B
 37 37  0  0  0  0  0  0  0  0999 V2000
   -6.1739    0.2663   -0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0594    0.7160   -0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1040    1.8686   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8397    0.5027    0.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6474   -0.1671   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5385   -0.2918    0.7983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3538   -0.8962    0.1485 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8636   -0.1886    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9326    0.9327    0.8545 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1240   -0.6793   -0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2260    0.3029   -0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5493   -0.1342   -0.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9344   -1.4173   -0.1133 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5497    0.9121   -0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5454    0.5768    0.3515 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3947    2.2196   -0.7650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9291   -1.3596    1.7915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3259   -2.4670    1.8701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9771   -1.1276    2.6489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8450    0.9055   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4927   -0.7593   -0.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6240    2.1679   -1.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4314    2.6606    0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9001    0.4599    1.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0141   -1.2008   -0.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3304    0.3581   -1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3119    0.6638    1.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -1.7852   -0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4005   -1.6284    0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0172   -0.8845   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3710    0.3203    1.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643    1.3167   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4372   -0.1778   -1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5127   -1.4930    0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9774   -1.4519   -0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2227    2.7484   -1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6990   -1.7891    2.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
  4  2  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 16 36  1  0
 19 37  1  0
M  END


  Mrv0541 02241218102D          

 19 19  0  0  0  0            999 V2000
   -1.2784    0.3708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833    1.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1957    1.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8659    2.5158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8659    3.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1244    2.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7006    2.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1244   -0.3708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9486   -0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2784   -1.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6180   -1.2784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2784   -2.6812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417   -3.3408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6180    0.5354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    1.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4534    1.8554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 15  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029428

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H18N2O5/c1-6-4-7(6)5-9(12(18)19)14-10(15)3-2-8(13)11(16)17/h7-9H,1-5,13H2,(H,14,15)(H,16,17)(H,18,19)

> <INCHI_KEY>
UYDZYCPIQSRXKU-UHFFFAOYSA-N

> <FORMULA>
C12H18N2O5

> <MOLECULAR_WEIGHT>
270.2817

> <EXACT_MASS>
270.121571696

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
26.957477564188057

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-{[1-carboxy-2-(2-methylidenecyclopropyl)ethyl]carbamoyl}butanoic acid

> <ALOGPS_LOGP>
-2.71

> <JCHEM_LOGP>
-3.0698129223581394

> <ALOGPS_LOGS>
-1.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.9269747571332205

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.824207283225891

> <JCHEM_PKA_STRONGEST_BASIC>
9.312076923754491

> <JCHEM_POLAR_SURFACE_AREA>
129.72

> <JCHEM_REFRACTIVITY>
64.78260000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-{[1-carboxy-2-(2-methylidenecyclopropyl)ethyl]carbamoyl}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029428
     RDKit          3D
Hypoglycin B
 37 37  0  0  0  0  0  0  0  0999 V2000
   -6.1739    0.2663   -0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0594    0.7160   -0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1040    1.8686   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8397    0.5027    0.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6474   -0.1671   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5385   -0.2918    0.7983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3538   -0.8962    0.1485 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8636   -0.1886    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9326    0.9327    0.8545 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1240   -0.6793   -0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2260    0.3029   -0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5493   -0.1342   -0.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9344   -1.4173   -0.1133 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5497    0.9121   -0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5454    0.5768    0.3515 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3947    2.2196   -0.7650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9291   -1.3596    1.7915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3259   -2.4670    1.8701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9771   -1.1276    2.6489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8450    0.9055   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4927   -0.7593   -0.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6240    2.1679   -1.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4314    2.6606    0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9001    0.4599    1.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0141   -1.2008   -0.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3304    0.3581   -1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3119    0.6638    1.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -1.7852   -0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4005   -1.6284    0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0172   -0.8845   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3710    0.3203    1.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643    1.3167   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4372   -0.1778   -1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5127   -1.4930    0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9774   -1.4519   -0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2227    2.7484   -1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6990   -1.7891    2.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
  4  2  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 16 36  1  0
 19 37  1  0
M  END

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  N   UNK     0      -2.386   0.692   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.462   2.078   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.232   3.463   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.616   4.696   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.616   6.236   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.232   5.466   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.308   5.466   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.232  -0.692   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.771  -0.692   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.386  -2.079   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.462  -3.465   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.076  -3.465   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.154  -2.386   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       2.386  -5.005   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.692  -5.005   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.078  -6.236   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.154   0.999   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.076   2.078   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.846   3.463   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    6                                                       
CONECT    6    4    5    7                                                  
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    1    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15   12   14   16                                                  
CONECT   16   15                                                            
CONECT   17   18                                                            
CONECT   18    2   17   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0029428
HETATM    1  C1  UNL     1      -6.174   0.266  -0.909  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.059   0.716  -0.365  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.104   1.869  -0.119  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.840   0.503   0.434  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.647  -0.167  -0.194  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.539  -0.292   0.798  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.354  -0.896   0.148  1.00  0.00           N  
HETATM    8  C7  UNL     1       0.864  -0.189   0.235  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.933   0.933   0.854  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.124  -0.679  -0.370  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.226   0.303  -0.078  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.549  -0.134  -0.667  1.00  0.00           C  
HETATM   13  N2  UNL     1       4.934  -1.417  -0.113  1.00  0.00           N  
HETATM   14  C11 UNL     1       5.550   0.912  -0.335  1.00  0.00           C  
HETATM   15  O2  UNL     1       6.545   0.577   0.351  1.00  0.00           O  
HETATM   16  O3  UNL     1       5.395   2.220  -0.765  1.00  0.00           O  
HETATM   17  C12 UNL     1      -1.929  -1.360   1.792  1.00  0.00           C  
HETATM   18  O4  UNL     1      -1.326  -2.467   1.870  1.00  0.00           O  
HETATM   19  O5  UNL     1      -2.977  -1.128   2.649  1.00  0.00           O  
HETATM   20  H1  UNL     1      -6.845   0.905  -1.499  1.00  0.00           H  
HETATM   21  H2  UNL     1      -6.493  -0.759  -0.806  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.624   2.168  -1.097  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.431   2.661   0.563  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.900   0.460   1.523  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.014  -1.201  -0.485  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.330   0.358  -1.131  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.312   0.664   1.264  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.425  -1.785  -0.338  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.401  -1.628   0.177  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.017  -0.885  -1.454  1.00  0.00           H  
HETATM   31  H12 UNL     1       3.371   0.320   1.033  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.964   1.317  -0.389  1.00  0.00           H  
HETATM   33  H14 UNL     1       4.437  -0.178  -1.785  1.00  0.00           H  
HETATM   34  H15 UNL     1       4.513  -1.493   0.843  1.00  0.00           H  
HETATM   35  H16 UNL     1       5.977  -1.452  -0.095  1.00  0.00           H  
HETATM   36  H17 UNL     1       6.223   2.748  -1.079  1.00  0.00           H  
HETATM   37  H18 UNL     1      -3.699  -1.789   2.881  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3    4
CONECT    3    4   22   23
CONECT    4    5   24
CONECT    5    6   25   26
CONECT    6    7   17   27
CONECT    7    8   28
CONECT    8    9    9   10
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   14   33
CONECT   13   34   35
CONECT   14   15   15   16
CONECT   16   36
CONECT   17   18   18   19
CONECT   19   37
END

HMDB0029428
     RDKit          3D
Hypoglycin B
 37 37  0  0  0  0  0  0  0  0999 V2000
   -6.1739    0.2663   -0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0594    0.7160   -0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1040    1.8686   -0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8397    0.5027    0.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6474   -0.1671   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5385   -0.2918    0.7983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3538   -0.8962    0.1485 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8636   -0.1886    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9326    0.9327    0.8545 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1240   -0.6793   -0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2260    0.3029   -0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5493   -0.1342   -0.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9344   -1.4173   -0.1133 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5497    0.9121   -0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5454    0.5768    0.3515 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3947    2.2196   -0.7650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9291   -1.3596    1.7915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3259   -2.4670    1.8701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9771   -1.1276    2.6489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8450    0.9055   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4927   -0.7593   -0.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6240    2.1679   -1.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4314    2.6606    0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9001    0.4599    1.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0141   -1.2008   -0.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3304    0.3581   -1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3119    0.6638    1.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -1.7852   -0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4005   -1.6284    0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0172   -0.8845   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3710    0.3203    1.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643    1.3167   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4372   -0.1778   -1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5127   -1.4930    0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9774   -1.4519   -0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2227    2.7484   -1.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6990   -1.7891    2.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
  4  2  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 16 36  1  0
 19 37  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Hypoglycine b	HMDB
L-gamma-Glutamyl-L-hypoglycin	HMDB
N-g-Glutamyl-3-(methylenecyclopropyl)alanine, 9ci	HMDB
2-Amino-4-{[1-carboxy-2-(2-methylidenecyclopropyl)ethyl]-C-hydroxycarbonimidoyl}butanoate	Generator

Chemical Formula

C₁₂H₁₈N₂O₅

Average Molecular Weight

270.2817

Monoisotopic Molecular Weight

270.121571696

IUPAC Name

2-amino-4-{[1-carboxy-2-(2-methylidenecyclopropyl)ethyl]carbamoyl}butanoic acid

Traditional Name

2-amino-4-{[1-carboxy-2-(2-methylidenecyclopropyl)ethyl]carbamoyl}butanoic acid

CAS Registry Number

502-37-4

SMILES

NC(CCC(=O)NC(CC1CC1=C)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C12H18N2O5/c1-6-4-7(6)5-9(12(18)19)14-10(15)3-2-8(13)11(16)17/h7-9H,1-5,13H2,(H,14,15)(H,16,17)(H,18,19)

InChI Key

UYDZYCPIQSRXKU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Gamma-glutamyl alpha-amino acid
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
Carbocyclic fatty acid
Dicarboxylic acid or derivatives
Fatty amide
Fatty acyl
N-acyl-amine
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Primary aliphatic amine
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029428)

Source

Endogenous

Endogenous (HMDB: HMDB0029428)

Plant

Animal

Animal (HMDB: HMDB0029428)

Exogenous

Food

Food (HMDB: HMDB0029428)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Metabolic Pathways (HMDB: HMDB0029428)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	200 - 207 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12.1 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-3.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.82	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	64.78 m³·mol⁻¹	ChemAxon
Polarizability	26.96 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	163.51	31661259
DarkChem	[M-H]-	157.519	31661259
DeepCCS	[M+H]+	157.489	30932474
DeepCCS	[M-H]-	155.131	30932474
DeepCCS	[M-2H]-	188.017	30932474
DeepCCS	[M+Na]+	163.582	30932474
AllCCS	[M+H]+	161.3	32859911
AllCCS	[M+H-H2O]+	158.3	32859911
AllCCS	[M+NH4]+	164.2	32859911
AllCCS	[M+Na]+	165.0	32859911
AllCCS	[M-H]-	162.1	32859911
AllCCS	[M+Na-2H]-	162.4	32859911
AllCCS	[M+HCOO]-	162.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hypoglycin B	NC(CCC(=O)NC(CC1CC1=C)C(O)=O)C(O)=O	3431.7	Standard polar	33892256
Hypoglycin B	NC(CCC(=O)NC(CC1CC1=C)C(O)=O)C(O)=O	2089.8	Standard non polar	33892256
Hypoglycin B	NC(CCC(=O)NC(CC1CC1=C)C(O)=O)C(O)=O	2544.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hypoglycin B,1TMS,isomer #1	C=C1CC1CC(NC(=O)CCC(N)C(=O)O)C(=O)O[Si](C)(C)C	2312.5	Semi standard non polar	33892256
Hypoglycin B,1TMS,isomer #2	C=C1CC1CC(NC(=O)CCC(N)C(=O)O[Si](C)(C)C)C(=O)O	2303.1	Semi standard non polar	33892256
Hypoglycin B,1TMS,isomer #3	C=C1CC1CC(NC(=O)CCC(N[Si](C)(C)C)C(=O)O)C(=O)O	2398.6	Semi standard non polar	33892256
Hypoglycin B,1TMS,isomer #4	C=C1CC1CC(C(=O)O)N(C(=O)CCC(N)C(=O)O)[Si](C)(C)C	2340.9	Semi standard non polar	33892256
Hypoglycin B,2TMS,isomer #1	C=C1CC1CC(NC(=O)CCC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2281.4	Semi standard non polar	33892256
Hypoglycin B,2TMS,isomer #2	C=C1CC1CC(NC(=O)CCC(N[Si](C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C	2382.9	Semi standard non polar	33892256
Hypoglycin B,2TMS,isomer #3	C=C1CC1CC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(N)C(=O)O)[Si](C)(C)C	2317.7	Semi standard non polar	33892256
Hypoglycin B,2TMS,isomer #4	C=C1CC1CC(NC(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O	2375.9	Semi standard non polar	33892256
Hypoglycin B,2TMS,isomer #5	C=C1CC1CC(C(=O)O)N(C(=O)CCC(N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2327.6	Semi standard non polar	33892256
Hypoglycin B,2TMS,isomer #6	C=C1CC1CC(C(=O)O)N(C(=O)CCC(N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2404.9	Semi standard non polar	33892256
Hypoglycin B,2TMS,isomer #7	C=C1CC1CC(NC(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2566.2	Semi standard non polar	33892256
Hypoglycin B,3TMS,isomer #1	C=C1CC1CC(NC(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2354.5	Semi standard non polar	33892256
Hypoglycin B,3TMS,isomer #1	C=C1CC1CC(NC(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2393.7	Standard non polar	33892256
Hypoglycin B,3TMS,isomer #2	C=C1CC1CC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2291.4	Semi standard non polar	33892256
Hypoglycin B,3TMS,isomer #2	C=C1CC1CC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2378.0	Standard non polar	33892256
Hypoglycin B,3TMS,isomer #3	C=C1CC1CC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2370.5	Semi standard non polar	33892256
Hypoglycin B,3TMS,isomer #3	C=C1CC1CC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2404.7	Standard non polar	33892256
Hypoglycin B,3TMS,isomer #4	C=C1CC1CC(NC(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2563.9	Semi standard non polar	33892256
Hypoglycin B,3TMS,isomer #4	C=C1CC1CC(NC(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2446.7	Standard non polar	33892256
Hypoglycin B,3TMS,isomer #5	C=C1CC1CC(C(=O)O)N(C(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2371.0	Semi standard non polar	33892256
Hypoglycin B,3TMS,isomer #5	C=C1CC1CC(C(=O)O)N(C(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2425.3	Standard non polar	33892256
Hypoglycin B,3TMS,isomer #6	C=C1CC1CC(NC(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2545.8	Semi standard non polar	33892256
Hypoglycin B,3TMS,isomer #6	C=C1CC1CC(NC(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2433.9	Standard non polar	33892256
Hypoglycin B,3TMS,isomer #7	C=C1CC1CC(C(=O)O)N(C(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2534.5	Semi standard non polar	33892256
Hypoglycin B,3TMS,isomer #7	C=C1CC1CC(C(=O)O)N(C(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2479.5	Standard non polar	33892256
Hypoglycin B,4TMS,isomer #1	C=C1CC1CC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2345.6	Semi standard non polar	33892256
Hypoglycin B,4TMS,isomer #1	C=C1CC1CC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2472.5	Standard non polar	33892256
Hypoglycin B,4TMS,isomer #2	C=C1CC1CC(NC(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2501.6	Semi standard non polar	33892256
Hypoglycin B,4TMS,isomer #2	C=C1CC1CC(NC(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2508.0	Standard non polar	33892256
Hypoglycin B,4TMS,isomer #3	C=C1CC1CC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2526.8	Semi standard non polar	33892256
Hypoglycin B,4TMS,isomer #3	C=C1CC1CC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2539.8	Standard non polar	33892256
Hypoglycin B,4TMS,isomer #4	C=C1CC1CC(C(=O)O)N(C(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2526.2	Semi standard non polar	33892256
Hypoglycin B,4TMS,isomer #4	C=C1CC1CC(C(=O)O)N(C(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2539.5	Standard non polar	33892256
Hypoglycin B,5TMS,isomer #1	C=C1CC1CC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2511.2	Semi standard non polar	33892256
Hypoglycin B,5TMS,isomer #1	C=C1CC1CC(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2592.1	Standard non polar	33892256
Hypoglycin B,1TBDMS,isomer #1	C=C1CC1CC(NC(=O)CCC(N)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2565.5	Semi standard non polar	33892256
Hypoglycin B,1TBDMS,isomer #2	C=C1CC1CC(NC(=O)CCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2555.4	Semi standard non polar	33892256
Hypoglycin B,1TBDMS,isomer #3	C=C1CC1CC(NC(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O	2645.7	Semi standard non polar	33892256
Hypoglycin B,1TBDMS,isomer #4	C=C1CC1CC(C(=O)O)N(C(=O)CCC(N)C(=O)O)[Si](C)(C)C(C)(C)C	2604.6	Semi standard non polar	33892256
Hypoglycin B,2TBDMS,isomer #1	C=C1CC1CC(NC(=O)CCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2763.6	Semi standard non polar	33892256
Hypoglycin B,2TBDMS,isomer #2	C=C1CC1CC(NC(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2861.7	Semi standard non polar	33892256
Hypoglycin B,2TBDMS,isomer #3	C=C1CC1CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(N)C(=O)O)[Si](C)(C)C(C)(C)C	2780.1	Semi standard non polar	33892256
Hypoglycin B,2TBDMS,isomer #4	C=C1CC1CC(NC(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2853.2	Semi standard non polar	33892256
Hypoglycin B,2TBDMS,isomer #5	C=C1CC1CC(C(=O)O)N(C(=O)CCC(N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2797.0	Semi standard non polar	33892256
Hypoglycin B,2TBDMS,isomer #6	C=C1CC1CC(C(=O)O)N(C(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2886.2	Semi standard non polar	33892256
Hypoglycin B,2TBDMS,isomer #7	C=C1CC1CC(NC(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3023.6	Semi standard non polar	33892256
Hypoglycin B,3TBDMS,isomer #1	C=C1CC1CC(NC(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3014.9	Semi standard non polar	33892256
Hypoglycin B,3TBDMS,isomer #1	C=C1CC1CC(NC(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2971.4	Standard non polar	33892256
Hypoglycin B,3TBDMS,isomer #2	C=C1CC1CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2964.7	Semi standard non polar	33892256
Hypoglycin B,3TBDMS,isomer #2	C=C1CC1CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2968.9	Standard non polar	33892256
Hypoglycin B,3TBDMS,isomer #3	C=C1CC1CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3055.0	Semi standard non polar	33892256
Hypoglycin B,3TBDMS,isomer #3	C=C1CC1CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2965.5	Standard non polar	33892256
Hypoglycin B,3TBDMS,isomer #4	C=C1CC1CC(NC(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3232.8	Semi standard non polar	33892256
Hypoglycin B,3TBDMS,isomer #4	C=C1CC1CC(NC(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2995.7	Standard non polar	33892256
Hypoglycin B,3TBDMS,isomer #5	C=C1CC1CC(C(=O)O)N(C(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3045.2	Semi standard non polar	33892256
Hypoglycin B,3TBDMS,isomer #5	C=C1CC1CC(C(=O)O)N(C(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2971.0	Standard non polar	33892256
Hypoglycin B,3TBDMS,isomer #6	C=C1CC1CC(NC(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3240.2	Semi standard non polar	33892256
Hypoglycin B,3TBDMS,isomer #6	C=C1CC1CC(NC(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3002.1	Standard non polar	33892256
Hypoglycin B,3TBDMS,isomer #7	C=C1CC1CC(C(=O)O)N(C(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3226.4	Semi standard non polar	33892256
Hypoglycin B,3TBDMS,isomer #7	C=C1CC1CC(C(=O)O)N(C(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3005.0	Standard non polar	33892256
Hypoglycin B,4TBDMS,isomer #1	C=C1CC1CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3207.9	Semi standard non polar	33892256
Hypoglycin B,4TBDMS,isomer #1	C=C1CC1CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3195.4	Standard non polar	33892256
Hypoglycin B,4TBDMS,isomer #2	C=C1CC1CC(NC(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3415.4	Semi standard non polar	33892256
Hypoglycin B,4TBDMS,isomer #2	C=C1CC1CC(NC(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3228.4	Standard non polar	33892256
Hypoglycin B,4TBDMS,isomer #3	C=C1CC1CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3417.4	Semi standard non polar	33892256
Hypoglycin B,4TBDMS,isomer #3	C=C1CC1CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3227.2	Standard non polar	33892256
Hypoglycin B,4TBDMS,isomer #4	C=C1CC1CC(C(=O)O)N(C(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3424.0	Semi standard non polar	33892256
Hypoglycin B,4TBDMS,isomer #4	C=C1CC1CC(C(=O)O)N(C(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3227.2	Standard non polar	33892256
Hypoglycin B,5TBDMS,isomer #1	C=C1CC1CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3607.0	Semi standard non polar	33892256
Hypoglycin B,5TBDMS,isomer #1	C=C1CC1CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3442.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hypoglycin B GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-9230000000-abf9f2628f7c6f3bf4c1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypoglycin B GC-MS (2 TMS) - 70eV, Positive	splash10-0v4l-9114000000-381c08f28fd0085766f5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypoglycin B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypoglycin B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypoglycin B 10V, Positive-QTOF	splash10-0fi0-1390000000-264246a6ebc82408f8af	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypoglycin B 20V, Positive-QTOF	splash10-056u-6970000000-7e42820d1c0dca334653	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypoglycin B 40V, Positive-QTOF	splash10-0pb9-9200000000-81a366aa1fbda762e1d6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypoglycin B 10V, Negative-QTOF	splash10-014i-0190000000-1477a66ca40d6a5e2212	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypoglycin B 20V, Negative-QTOF	splash10-0kxu-2790000000-b364e7c8f259fffd1a10	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypoglycin B 40V, Negative-QTOF	splash10-006x-9400000000-6aab591feaaac89bc93f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypoglycin B 10V, Positive-QTOF	splash10-00di-2390000000-514b84378308aa29dab6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypoglycin B 20V, Positive-QTOF	splash10-001j-9310000000-6f7ee1b689a75066e051	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypoglycin B 40V, Positive-QTOF	splash10-001i-9000000000-8bd6d39da96e91345c65	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypoglycin B 10V, Negative-QTOF	splash10-0gbc-1490000000-d146ac33ac4dde2ed7fb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypoglycin B 20V, Negative-QTOF	splash10-00vl-4950000000-d04166d53bc496aa778d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypoglycin B 40V, Negative-QTOF	splash10-0006-9200000000-fb3a089478f48fb74cb5	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hypoglycin B

METLIN ID

Not Available

PubChem Compound

108105

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Hypoglycin B (HMDB0029428)

MOL for HMDB0029428 (Hypoglycin B)

3D MOL for HMDB0029428 (Hypoglycin B)

3D SDF for HMDB0029428 (Hypoglycin B)

3D-SDF for HMDB0029428 (Hypoglycin B)

PDB for HMDB0029428 (Hypoglycin B)

3D PDB for HMDB0029428 (Hypoglycin B)

SMILES for HMDB0029428 (Hypoglycin B)

INCHI for HMDB0029428 (Hypoglycin B)

Structure for HMDB0029428 (Hypoglycin B)

3D Structure for HMDB0029428 (Hypoglycin B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra