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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:59:51 UTC

Update Date

2022-03-07 02:56:58 UTC

HMDB ID

HMDB0041329

Secondary Accession Numbers

HMDB41329

Metabolite Identification

Common Name

5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone

Description

5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Based on a literature review very few articles have been published on 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone.

Structure

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

HMDB0041329
     RDKit          3D
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone
 37 38  0  0  0  0  0  0  0  0999 V2000
   -3.8244   -1.0444   -1.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7566   -0.3372    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0093   -0.5132    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4839    1.1373   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1897    1.2280   -0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834    1.8715   -1.9729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0469    0.5091   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711   -0.5070    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3265   -1.1832    1.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0015   -0.8795    0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3059    0.1259   -0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711    0.4537   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9372    1.3845   -1.1130 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7649   -0.2736    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394    0.0136    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1459   -0.7379    0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9127    0.1731    1.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432    0.8261   -0.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5184    1.8780   -1.5035 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6775   -0.8601    0.8820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8318   -1.5511   -1.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9871   -0.3457   -2.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5652   -1.8819   -1.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8208   -0.8127    0.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2803    0.4203    1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9044   -1.3010    1.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5065    1.6850    0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3285    1.4658   -0.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5615   -1.9988    1.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7338   -1.5021    1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6264   -1.0865    0.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2240    0.8212   -0.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7050   -1.5315    1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7713   -1.2517   -0.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6381    1.0981    1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3035    1.7153   -2.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9131    2.7927   -1.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 11 18  2  0
 18 19  1  0
  8 20  1  0
 20  2  1  0
 18  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
M  END


  Mrv0541 05061312352D          

 20 21  0  0  0  0            999 V2000
    5.0993    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690   -0.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  9  5  1  0  0  0  0
 10  4  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 13 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14  9  2  0  0  0  0
 14 13  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  8  1  0  0  0  0
 16 14  1  0  0  0  0
 17  7  1  0  0  0  0
 18 10  2  0  0  0  0
 19 11  2  0  0  0  0
 20 12  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041329

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)CC(=O)C2=C(O1)C=CC(C(=O)\C=C\CO)=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C15H17NO4/c1-15(2)8-11(19)13-12(20-15)6-5-9(14(13)16)10(18)4-3-7-17/h3-6,17H,7-8,16H2,1-2H3/b4-3+

> <INCHI_KEY>
FQWVFPQMOJOLSZ-ONEGZZNKSA-N

> <FORMULA>
C15H17NO4

> <MOLECULAR_WEIGHT>
275.2998

> <EXACT_MASS>
275.115758037

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.465032858939956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-amino-6-[(2E)-4-hydroxybut-2-enoyl]-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
1.8995939306666667

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.571978406172846

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.861605520308895

> <JCHEM_PKA_STRONGEST_BASIC>
0.6337320953942218

> <JCHEM_POLAR_SURFACE_AREA>
89.62

> <JCHEM_REFRACTIVITY>
77.32039999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-amino-6-[(2E)-4-hydroxybut-2-enoyl]-2,2-dimethyl-3H-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041329
     RDKit          3D
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone
 37 38  0  0  0  0  0  0  0  0999 V2000
   -3.8244   -1.0444   -1.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7566   -0.3372    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0093   -0.5132    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4839    1.1373   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1897    1.2280   -0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834    1.8715   -1.9729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0469    0.5091   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711   -0.5070    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3265   -1.1832    1.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0015   -0.8795    0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3059    0.1259   -0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711    0.4537   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9372    1.3845   -1.1130 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7649   -0.2736    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394    0.0136    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1459   -0.7379    0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9127    0.1731    1.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432    0.8261   -0.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5184    1.8780   -1.5035 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6775   -0.8601    0.8820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8318   -1.5511   -1.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9871   -0.3457   -2.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5652   -1.8819   -1.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8208   -0.8127    0.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2803    0.4203    1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9044   -1.3010    1.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5065    1.6850    0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3285    1.4658   -0.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5615   -1.9988    1.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7338   -1.5021    1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6264   -1.0865    0.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2240    0.8212   -0.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7050   -1.5315    1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7713   -1.2517   -0.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6381    1.0981    1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3035    1.7153   -2.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9131    2.7927   -1.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 11 18  2  0
 18 19  1  0
  8 20  1  0
 20  2  1  0
 18  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
M  END

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       9.519   0.267   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.529  -1.447   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       4.001   3.850   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3    4    7                                                       
CONECT    4    3   10                                                       
CONECT    5    6    9                                                       
CONECT    6    5   12                                                       
CONECT    7    3   17                                                       
CONECT    8   11   15                                                       
CONECT    9    5   10   14                                                  
CONECT   10    4    9   18                                                  
CONECT   11    8   13   19                                                  
CONECT   12    6   13   20                                                  
CONECT   13   11   12   14                                                  
CONECT   14    9   13   16                                                  
CONECT   15    1    2    8   20                                             
CONECT   16   14                                                            
CONECT   17    7                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0041329
HETATM    1  C1  UNL     1      -3.824  -1.044  -1.242  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.757  -0.337   0.101  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.009  -0.513   0.898  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.484   1.137  -0.221  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.190   1.228  -0.911  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.983   1.872  -1.973  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.047   0.509  -0.311  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.371  -0.507   0.563  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.326  -1.183   1.127  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.002  -0.879   0.850  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.306   0.126  -0.014  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.671   0.454  -0.313  1.00  0.00           C  
HETATM   13  O2  UNL     1       2.937   1.385  -1.113  1.00  0.00           O  
HETATM   14  C12 UNL     1       3.765  -0.274   0.295  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.039   0.014   0.032  1.00  0.00           C  
HETATM   16  C14 UNL     1       6.146  -0.738   0.660  1.00  0.00           C  
HETATM   17  O3  UNL     1       6.913   0.173   1.387  1.00  0.00           O  
HETATM   18  C15 UNL     1       0.243   0.826  -0.599  1.00  0.00           C  
HETATM   19  N1  UNL     1       0.518   1.878  -1.503  1.00  0.00           N  
HETATM   20  O4  UNL     1      -2.677  -0.860   0.882  1.00  0.00           O  
HETATM   21  H1  UNL     1      -2.832  -1.551  -1.385  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.987  -0.346  -2.066  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.565  -1.882  -1.225  1.00  0.00           H  
HETATM   24  H4  UNL     1      -5.821  -0.813   0.186  1.00  0.00           H  
HETATM   25  H5  UNL     1      -5.280   0.420   1.427  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.904  -1.301   1.689  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.507   1.685   0.752  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.329   1.466  -0.845  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.561  -1.999   1.828  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.734  -1.502   1.373  1.00  0.00           H  
HETATM   31  H11 UNL     1       3.626  -1.087   0.992  1.00  0.00           H  
HETATM   32  H12 UNL     1       5.224   0.821  -0.661  1.00  0.00           H  
HETATM   33  H13 UNL     1       5.705  -1.531   1.295  1.00  0.00           H  
HETATM   34  H14 UNL     1       6.771  -1.252  -0.103  1.00  0.00           H  
HETATM   35  H15 UNL     1       6.638   1.098   1.231  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.304   1.715  -2.520  1.00  0.00           H  
HETATM   37  H17 UNL     1       0.913   2.793  -1.247  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4   20
CONECT    3   24   25   26
CONECT    4    5   27   28
CONECT    5    6    6    7
CONECT    7    8    8   18
CONECT    8    9   20
CONECT    9   10   10   29
CONECT   10   11   30
CONECT   11   12   18   18
CONECT   12   13   13   14
CONECT   14   15   15   31
CONECT   15   16   32
CONECT   16   17   33   34
CONECT   17   35
CONECT   18   19
CONECT   19   36   37
END

HMDB0041329
     RDKit          3D
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone
 37 38  0  0  0  0  0  0  0  0999 V2000
   -3.8244   -1.0444   -1.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7566   -0.3372    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0093   -0.5132    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4839    1.1373   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1897    1.2280   -0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834    1.8715   -1.9729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0469    0.5091   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711   -0.5070    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3265   -1.1832    1.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0015   -0.8795    0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3059    0.1259   -0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711    0.4537   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9372    1.3845   -1.1130 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7649   -0.2736    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394    0.0136    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1459   -0.7379    0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9127    0.1731    1.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432    0.8261   -0.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5184    1.8780   -1.5035 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6775   -0.8601    0.8820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8318   -1.5511   -1.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9871   -0.3457   -2.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5652   -1.8819   -1.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8208   -0.8127    0.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2803    0.4203    1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9044   -1.3010    1.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5065    1.6850    0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3285    1.4658   -0.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5615   -1.9988    1.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7338   -1.5021    1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6264   -1.0865    0.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2240    0.8212   -0.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7050   -1.5315    1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7713   -1.2517   -0.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6381    1.0981    1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3035    1.7153   -2.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9131    2.7927   -1.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 11 18  2  0
 18 19  1  0
  8 20  1  0
 20  2  1  0
 18  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₇NO₄

Average Molecular Weight

275.2998

Monoisotopic Molecular Weight

275.115758037

IUPAC Name

5-amino-6-[(2E)-4-hydroxybut-2-enoyl]-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

5-amino-6-[(2E)-4-hydroxybut-2-enoyl]-2,2-dimethyl-3H-1-benzopyran-4-one

CAS Registry Number

162287-97-0

SMILES

CC1(C)CC(=O)C2=C(O1)C=CC(C(=O)\C=C\CO)=C2N

InChI Identifier

InChI=1S/C15H17NO4/c1-15(2)8-11(19)13-12(20-15)6-5-9(14(13)16)10(18)4-3-7-17/h3-6,17H,7-8,16H2,1-2H3/b4-3+

InChI Key

FQWVFPQMOJOLSZ-ONEGZZNKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
Chromone
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Benzenoid
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Vinylogous amide
Ketone
Ether
Oxacycle
Organic oxide
Organopnictogen compound
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041329)
Cytoplasm (HMDB: HMDB0041329)

Source

Exogenous

Food

Food (HMDB: HMDB0041329)

Not Available

Nutrient (HMDB: HMDB0041329)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	0.18 g/L	ALOGPS
logP	2.24	ALOGPS
logP	1.9	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	14.86	ChemAxon
pKa (Strongest Basic)	0.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.62 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	77.32 m³·mol⁻¹	ChemAxon
Polarizability	29.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DeepCCS	[M+H]+	164.26	30932474
DeepCCS	[M-H]-	161.902	30932474
DeepCCS	[M-2H]-	195.153	30932474
DeepCCS	[M+Na]+	170.381	30932474
AllCCS	[M+H]+	164.0	32859911
AllCCS	[M+H-H2O]+	160.4	32859911
AllCCS	[M+NH4]+	167.4	32859911
AllCCS	[M+Na]+	168.3	32859911
AllCCS	[M-H]-	167.7	32859911
AllCCS	[M+Na-2H]-	167.8	32859911
AllCCS	[M+HCOO]-	168.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone	CC1(C)CC(=O)C2=C(O1)C=CC(C(=O)\C=C\CO)=C2N	3811.9	Standard polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone	CC1(C)CC(=O)C2=C(O1)C=CC(C(=O)\C=C\CO)=C2N	2524.0	Standard non polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone	CC1(C)CC(=O)C2=C(O1)C=CC(C(=O)\C=C\CO)=C2N	2559.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone,1TMS,isomer #1	CC1(C)CC(=O)C2=C(C=CC(C(=O)/C=C/CO[Si](C)(C)C)=C2N)O1	2556.8	Semi standard non polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone,1TMS,isomer #2	CC1(C)CC(=O)C2=C(C=CC(C(=O)/C=C/CO)=C2N[Si](C)(C)C)O1	2533.1	Semi standard non polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone,2TMS,isomer #1	CC1(C)CC(=O)C2=C(C=CC(C(=O)/C=C/CO[Si](C)(C)C)=C2N[Si](C)(C)C)O1	2597.7	Semi standard non polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone,2TMS,isomer #1	CC1(C)CC(=O)C2=C(C=CC(C(=O)/C=C/CO[Si](C)(C)C)=C2N[Si](C)(C)C)O1	2623.7	Standard non polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone,2TMS,isomer #2	CC1(C)CC(=O)C2=C(C=CC(C(=O)/C=C/CO)=C2N([Si](C)(C)C)[Si](C)(C)C)O1	2434.1	Semi standard non polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone,2TMS,isomer #2	CC1(C)CC(=O)C2=C(C=CC(C(=O)/C=C/CO)=C2N([Si](C)(C)C)[Si](C)(C)C)O1	2648.4	Standard non polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone,3TMS,isomer #1	CC1(C)CC(=O)C2=C(C=CC(C(=O)/C=C/CO[Si](C)(C)C)=C2N([Si](C)(C)C)[Si](C)(C)C)O1	2525.7	Semi standard non polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone,3TMS,isomer #1	CC1(C)CC(=O)C2=C(C=CC(C(=O)/C=C/CO[Si](C)(C)C)=C2N([Si](C)(C)C)[Si](C)(C)C)O1	2675.6	Standard non polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone,1TBDMS,isomer #1	CC1(C)CC(=O)C2=C(C=CC(C(=O)/C=C/CO[Si](C)(C)C(C)(C)C)=C2N)O1	2802.3	Semi standard non polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone,1TBDMS,isomer #2	CC1(C)CC(=O)C2=C(C=CC(C(=O)/C=C/CO)=C2N[Si](C)(C)C(C)(C)C)O1	2786.2	Semi standard non polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone,2TBDMS,isomer #1	CC1(C)CC(=O)C2=C(C=CC(C(=O)/C=C/CO[Si](C)(C)C(C)(C)C)=C2N[Si](C)(C)C(C)(C)C)O1	3057.9	Semi standard non polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone,2TBDMS,isomer #1	CC1(C)CC(=O)C2=C(C=CC(C(=O)/C=C/CO[Si](C)(C)C(C)(C)C)=C2N[Si](C)(C)C(C)(C)C)O1	3050.3	Standard non polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone,2TBDMS,isomer #2	CC1(C)CC(=O)C2=C(C=CC(C(=O)/C=C/CO)=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O1	2942.8	Semi standard non polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone,2TBDMS,isomer #2	CC1(C)CC(=O)C2=C(C=CC(C(=O)/C=C/CO)=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O1	3085.1	Standard non polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone,3TBDMS,isomer #1	CC1(C)CC(=O)C2=C(C=CC(C(=O)/C=C/CO[Si](C)(C)C(C)(C)C)=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O1	3206.3	Semi standard non polar	33892256
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone,3TBDMS,isomer #1	CC1(C)CC(=O)C2=C(C=CC(C(=O)/C=C/CO[Si](C)(C)C(C)(C)C)=C2N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O1	3304.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1190000000-4d77bfe7d832595c0614	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone GC-MS (1 TMS) - 70eV, Positive	splash10-00gi-9243000000-3d5d368291fcd17faa60	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone 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 - 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone 10V, Positive-QTOF	splash10-0a6r-1090000000-fd5305d8ddcc473809c7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone 20V, Positive-QTOF	splash10-052f-3090000000-be2f6a250733144747a3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone 40V, Positive-QTOF	splash10-0a4i-9220000000-11849690e678f4daa60c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone 10V, Negative-QTOF	splash10-00di-0090000000-7ba0128ecf797a8c5338	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone 20V, Negative-QTOF	splash10-0abc-2290000000-3eb237bd9eaf7517116c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone 40V, Negative-QTOF	splash10-05fu-6920000000-cd62c03d8a4bb2a9acbb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone 10V, Negative-QTOF	splash10-00e9-0090000000-49a1a8577078e46f5104	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone 20V, Negative-QTOF	splash10-0006-0980000000-064aed188f6606536a4a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone 40V, Negative-QTOF	splash10-00fr-1950000000-21926900970b3507a882	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone 10V, Positive-QTOF	splash10-004i-0090000000-e44492a9d92cb07b078d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone 20V, Positive-QTOF	splash10-00o3-0190000000-2bb5427a7075f99aa06f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone 40V, Positive-QTOF	splash10-00fr-1920000000-cf0cb04775a97399b998	2021-09-25	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

FDB021252

KNApSAcK ID

C00055099

Chemspider ID

30777559

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15225569

PDB ID

Not Available

ChEBI ID

174629

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 5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone (HMDB0041329)

MOL for HMDB0041329 (5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone)

3D MOL for HMDB0041329 (5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone)

3D SDF for HMDB0041329 (5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone)

3D-SDF for HMDB0041329 (5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone)

PDB for HMDB0041329 (5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone)

3D PDB for HMDB0041329 (5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone)

SMILES for HMDB0041329 (5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone)

INCHI for HMDB0041329 (5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone)

Structure for HMDB0041329 (5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone)

3D Structure for HMDB0041329 (5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra