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Showing metabocard for (2R,2'S)-Isobuteine (HMDB0030411)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:38 UTC
Update Date2022-03-07 02:52:32 UTC
HMDB IDHMDB0030411
Secondary Accession Numbers
  • HMDB30411
Metabolite Identification
Common Name(2R,2'S)-Isobuteine
Description(2R,2'S)-Isobuteine belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on (2R,2'S)-Isobuteine.
Structure
Data?1563861981
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0030411 ((2R,2'S)-Isobuteine)


  Mrv0541 05061305132D          

 13 12  0  0  0  0            999 V2000
   -0.9355   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -0.1914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -1.0164    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13  2  1  0  0  0  0
 13  3  1  0  0  0  0
M  END
Download

3D MOL for HMDB0030411 ((2R,2'S)-Isobuteine)

HMDB0030411
     RDKit          3D
(2R,2'S)-Isobuteine
 26 25  0  0  0  0  0  0  0  0999 V2000
   -2.3727    0.7010    1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3921   -0.1016    0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1353    0.0813   -0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3385   -0.4319    0.1957 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7730   -0.1552   -0.8639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0686   -0.5602   -0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -1.9409    0.1619 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2915    0.3495    0.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4845   -0.1216    2.0785 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2858    1.7070    0.7428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5461    0.3208   -0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3483    0.7946   -1.8823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8556    0.2142   -0.2943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0294    0.0879    2.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6890    1.5703    1.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4221    1.0036    1.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5300   -1.1640    0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703    1.1530   -1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399   -0.4969   -1.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6059   -0.7310   -1.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    0.9081   -1.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8730   -0.3844   -0.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6181   -2.5489   -0.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9263   -2.1352    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6708    2.4047    1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1937   -0.5244    0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 13 26  1  0
M  END
Download

3D SDF for HMDB0030411 ((2R,2'S)-Isobuteine)


  Mrv0541 05061305132D          

 13 12  0  0  0  0            999 V2000
   -0.9355   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -0.1914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3645   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4934   -1.0164    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13  2  1  0  0  0  0
 13  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030411

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CSCC(N)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO4S/c1-4(6(9)10)2-13-3-5(8)7(11)12/h4-5H,2-3,8H2,1H3,(H,9,10)(H,11,12)

> <INCHI_KEY>
QSPWUNSFUXUUDG-UHFFFAOYSA-N

> <FORMULA>
C7H13NO4S

> <MOLECULAR_WEIGHT>
207.247

> <EXACT_MASS>
207.056528599

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
20.59806022747814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid

> <ALOGPS_LOGP>
-2.49

> <JCHEM_LOGP>
-2.307267739540217

> <ALOGPS_LOGS>
-1.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.3781447094705745

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.078315521558558

> <JCHEM_PKA_STRONGEST_BASIC>
9.14232944076914

> <JCHEM_POLAR_SURFACE_AREA>
100.62000000000002

> <JCHEM_REFRACTIVITY>
48.2823

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0030411 ((2R,2'S)-Isobuteine)

HMDB0030411
     RDKit          3D
(2R,2'S)-Isobuteine
 26 25  0  0  0  0  0  0  0  0999 V2000
   -2.3727    0.7010    1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3921   -0.1016    0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1353    0.0813   -0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3385   -0.4319    0.1957 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7730   -0.1552   -0.8639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0686   -0.5602   -0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -1.9409    0.1619 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2915    0.3495    0.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4845   -0.1216    2.0785 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2858    1.7070    0.7428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5461    0.3208   -0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3483    0.7946   -1.8823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8556    0.2142   -0.2943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0294    0.0879    2.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6890    1.5703    1.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4221    1.0036    1.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5300   -1.1640    0.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703    1.1530   -1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399   -0.4969   -1.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6059   -0.7310   -1.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    0.9081   -1.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8730   -0.3844   -0.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6181   -2.5489   -0.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9263   -2.1352    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6708    2.4047    1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1937   -0.5244    0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 13 26  1  0
M  END
Download

PDB for HMDB0030411 ((2R,2'S)-Isobuteine)

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      -1.746  -0.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.413  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.255  -2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.746  -1.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.588  -1.897   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.922  -2.667   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.588  -0.357   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      -4.414  -1.897   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -3.080  -4.207   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.256  -1.897   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.922  -4.207   0.000  0.00  0.00           O+0
HETATM   13  S   UNK     0       0.921  -1.897   0.000  0.00  0.00           S+0
CONECT    1    4                                                            
CONECT    2    4   13                                                       
CONECT    3    5   13                                                       
CONECT    4    1    2    6                                                  
CONECT    5    3    7    8                                                  
CONECT    6    4    9   10                                                  
CONECT    7    5   11   12                                                  
CONECT    8    5                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    7                                                            
CONECT   13    2    3                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for HMDB0030411 ((2R,2'S)-Isobuteine)

COMPND    HMDB0030411
HETATM    1  C1  UNL     1      -2.373   0.701   1.377  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.392  -0.102   0.087  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.135   0.081  -0.693  1.00  0.00           C  
HETATM    4  S1  UNL     1       0.338  -0.432   0.196  1.00  0.00           S  
HETATM    5  C4  UNL     1       1.773  -0.155  -0.864  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.069  -0.560  -0.197  1.00  0.00           C  
HETATM    7  N1  UNL     1       3.103  -1.941   0.162  1.00  0.00           N  
HETATM    8  C6  UNL     1       3.291   0.349   0.940  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.485  -0.122   2.078  1.00  0.00           O  
HETATM   10  O2  UNL     1       3.286   1.707   0.743  1.00  0.00           O  
HETATM   11  C7  UNL     1      -3.546   0.321  -0.738  1.00  0.00           C  
HETATM   12  O3  UNL     1      -3.348   0.795  -1.882  1.00  0.00           O  
HETATM   13  O4  UNL     1      -4.856   0.214  -0.294  1.00  0.00           O  
HETATM   14  H1  UNL     1      -2.029   0.088   2.244  1.00  0.00           H  
HETATM   15  H2  UNL     1      -1.689   1.570   1.322  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.422   1.004   1.606  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.530  -1.164   0.393  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.070   1.153  -1.002  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.240  -0.497  -1.641  1.00  0.00           H  
HETATM   20  H7  UNL     1       1.606  -0.731  -1.817  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.786   0.908  -1.151  1.00  0.00           H  
HETATM   22  H9  UNL     1       3.873  -0.384  -0.945  1.00  0.00           H  
HETATM   23  H10 UNL     1       2.618  -2.549  -0.503  1.00  0.00           H  
HETATM   24  H11 UNL     1       2.926  -2.135   1.159  1.00  0.00           H  
HETATM   25  H12 UNL     1       3.671   2.405   1.335  1.00  0.00           H  
HETATM   26  H13 UNL     1      -5.194  -0.524   0.300  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   11   17
CONECT    3    4   18   19
CONECT    4    5
CONECT    5    6   20   21
CONECT    6    7    8   22
CONECT    7   23   24
CONECT    8    9    9   10
CONECT   10   25
CONECT   11   12   12   13
CONECT   13   26
END
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SMILES for HMDB0030411 ((2R,2'S)-Isobuteine)

CC(CSCC(N)C(O)=O)C(O)=O
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INCHI for HMDB0030411 ((2R,2'S)-Isobuteine)

InChI=1S/C7H13NO4S/c1-4(6(9)10)2-13-3-5(8)7(11)12/h4-5H,2-3,8H2,1H3,(H,9,10)(H,11,12)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
S-(2-Carboxypropyl)cysteineHMDB
S-(2-Carboxypropyl)cysteine, (D)-isomerHMDB
2-Amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoateHMDB
2-Amino-3-[(2-carboxy-2-methylethyl)sulphanyl]propanoateHMDB
2-Amino-3-[(2-carboxy-2-methylethyl)sulphanyl]propanoic acidHMDB
Chemical FormulaC7H13NO4S
Average Molecular Weight207.247
Monoisotopic Molecular Weight207.056528599
IUPAC Name2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid
Traditional Name2-amino-3-[(2-carboxy-2-methylethyl)sulfanyl]propanoic acid
CAS Registry Number66512-75-2
SMILES
CC(CSCC(N)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H13NO4S/c1-4(6(9)10)2-13-3-5(8)7(11)12/h4-5H,2-3,8H2,1H3,(H,9,10)(H,11,12)
InChI KeyQSPWUNSFUXUUDG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCysteine and derivatives
Alternative Parents
Substituents
  • Cysteine or derivatives
  • Alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Amine
  • Organic nitrogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point196 - 198 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility12.5 g/LALOGPS
logP-2.5ALOGPS
logP-2.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)2.08ChemAxon
pKa (Strongest Basic)9.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity48.28 m³·mol⁻¹ChemAxon
Polarizability20.6 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.1131661259
DarkChem[M-H]-138.84231661259
DeepCCS[M+H]+141.65830932474
DeepCCS[M-H]-137.63230932474
DeepCCS[M-2H]-175.20130932474
DeepCCS[M+Na]+150.81430932474
AllCCS[M+H]+144.432859911
AllCCS[M+H-H2O]+141.032859911
AllCCS[M+NH4]+147.632859911
AllCCS[M+Na]+148.532859911
AllCCS[M-H]-143.632859911
AllCCS[M+Na-2H]-145.032859911
AllCCS[M+HCOO]-146.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. 1.81 minutes32390414
Predicted by Siyang on May 30, 202210.0551 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20228.34 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid406.5 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid845.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid295.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid40.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid170.3 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid64.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid276.5 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid257.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)732.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid621.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid58.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid868.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid175.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid180.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate511.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA382.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water381.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(2R,2'S)-IsobuteineCC(CSCC(N)C(O)=O)C(O)=O2855.0Standard polar33892256
(2R,2'S)-IsobuteineCC(CSCC(N)C(O)=O)C(O)=O1585.7Standard non polar33892256
(2R,2'S)-IsobuteineCC(CSCC(N)C(O)=O)C(O)=O1967.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(2R,2'S)-Isobuteine,1TMS,isomer #1CC(CSCC(N)C(=O)O[Si](C)(C)C)C(=O)O1838.5Semi standard non polar33892256
(2R,2'S)-Isobuteine,1TMS,isomer #2CC(CSCC(N)C(=O)O)C(=O)O[Si](C)(C)C1835.2Semi standard non polar33892256
(2R,2'S)-Isobuteine,1TMS,isomer #3CC(CSCC(N[Si](C)(C)C)C(=O)O)C(=O)O1894.7Semi standard non polar33892256
(2R,2'S)-Isobuteine,2TMS,isomer #1CC(CSCC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1879.1Semi standard non polar33892256
(2R,2'S)-Isobuteine,2TMS,isomer #2CC(CSCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O1910.0Semi standard non polar33892256
(2R,2'S)-Isobuteine,2TMS,isomer #3CC(CSCC(N[Si](C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C1924.4Semi standard non polar33892256
(2R,2'S)-Isobuteine,2TMS,isomer #4CC(CSCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2076.6Semi standard non polar33892256
(2R,2'S)-Isobuteine,3TMS,isomer #1CC(CSCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1940.8Semi standard non polar33892256
(2R,2'S)-Isobuteine,3TMS,isomer #1CC(CSCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1931.0Standard non polar33892256
(2R,2'S)-Isobuteine,3TMS,isomer #2CC(CSCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2070.0Semi standard non polar33892256
(2R,2'S)-Isobuteine,3TMS,isomer #2CC(CSCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2013.4Standard non polar33892256
(2R,2'S)-Isobuteine,3TMS,isomer #3CC(CSCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2081.5Semi standard non polar33892256
(2R,2'S)-Isobuteine,3TMS,isomer #3CC(CSCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2021.1Standard non polar33892256
(2R,2'S)-Isobuteine,4TMS,isomer #1CC(CSCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2096.2Semi standard non polar33892256
(2R,2'S)-Isobuteine,4TMS,isomer #1CC(CSCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2068.2Standard non polar33892256
(2R,2'S)-Isobuteine,1TBDMS,isomer #1CC(CSCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2107.2Semi standard non polar33892256
(2R,2'S)-Isobuteine,1TBDMS,isomer #2CC(CSCC(N)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2103.1Semi standard non polar33892256
(2R,2'S)-Isobuteine,1TBDMS,isomer #3CC(CSCC(N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O2151.1Semi standard non polar33892256
(2R,2'S)-Isobuteine,2TBDMS,isomer #1CC(CSCC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2343.7Semi standard non polar33892256
(2R,2'S)-Isobuteine,2TBDMS,isomer #2CC(CSCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2385.9Semi standard non polar33892256
(2R,2'S)-Isobuteine,2TBDMS,isomer #3CC(CSCC(N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2393.6Semi standard non polar33892256
(2R,2'S)-Isobuteine,2TBDMS,isomer #4CC(CSCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2501.2Semi standard non polar33892256
(2R,2'S)-Isobuteine,3TBDMS,isomer #1CC(CSCC(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)C2612.7Semi standard non polar33892256
(2R,2'S)-Isobuteine,3TBDMS,isomer #1CC(CSCC(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)C2538.2Standard non polar33892256
(2R,2'S)-Isobuteine,3TBDMS,isomer #2CC(CSCC(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)O2759.8Semi standard non polar33892256
(2R,2'S)-Isobuteine,3TBDMS,isomer #2CC(CSCC(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)O2611.1Standard non polar33892256
(2R,2'S)-Isobuteine,3TBDMS,isomer #3CC(CSCC(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)C2758.7Semi standard non polar33892256
(2R,2'S)-Isobuteine,3TBDMS,isomer #3CC(CSCC(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)C2613.6Standard non polar33892256
(2R,2'S)-Isobuteine,4TBDMS,isomer #1CC(CSCC(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)C2974.8Semi standard non polar33892256
(2R,2'S)-Isobuteine,4TBDMS,isomer #1CC(CSCC(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)C2815.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (2R,2'S)-Isobuteine GC-MS (Non-derivatized) - 70eV, Positivesplash10-01vx-9400000000-8a8a2eaf38f8addb05862017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (2R,2'S)-Isobuteine GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9212000000-28650ad5f3a136d2ba6a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (2R,2'S)-Isobuteine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (2R,2'S)-Isobuteine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,2'S)-Isobuteine 10V, Positive-QTOFsplash10-06rl-6920000000-467a5d7ad69ac4c5e3b02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,2'S)-Isobuteine 20V, Positive-QTOFsplash10-00du-9800000000-84418ae3835adf0e1bcb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,2'S)-Isobuteine 40V, Positive-QTOFsplash10-0076-9100000000-6f05adfb74349f5f4b382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,2'S)-Isobuteine 10V, Negative-QTOFsplash10-05g0-3930000000-988d57c96e2ceeaff7482016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,2'S)-Isobuteine 20V, Negative-QTOFsplash10-00y0-7900000000-899ea16a4ed1d77d4be22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,2'S)-Isobuteine 40V, Negative-QTOFsplash10-000i-9200000000-0a9991dfb43ebd9428062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,2'S)-Isobuteine 10V, Positive-QTOFsplash10-00di-0910000000-c4b5548724a676c0fbe12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,2'S)-Isobuteine 20V, Positive-QTOFsplash10-00di-9700000000-0f48eb5017165c0ec77b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,2'S)-Isobuteine 40V, Positive-QTOFsplash10-00di-9000000000-5d3fea24933f35dd03ea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,2'S)-Isobuteine 10V, Negative-QTOFsplash10-00ei-9700000000-85cd1359d8a7e43fd7312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,2'S)-Isobuteine 20V, Negative-QTOFsplash10-001i-9300000000-2f790882879516d6026a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,2'S)-Isobuteine 40V, Negative-QTOFsplash10-004i-9000000000-821e87a136f838fd7fd62021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002273
KNApSAcK IDNot Available
Chemspider ID13664198
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14889929
PDB IDNot Available
ChEBI ID172450
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .