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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:18:11 UTC

Update Date

2022-03-07 02:56:00 UTC

HMDB ID

HMDB0038956

Secondary Accession Numbers

HMDB38956

Metabolite Identification

Common Name

Avenalumin III

Description

Avenalumin III belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom). Avenalumin III has been detected, but not quantified in, a few different foods, such as breakfast cereal, cereals and cereal products, and oats (Avena sativa). This could make avenalumin III a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Avenalumin III.

Structure

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

HMDB0038956
     RDKit          3D
Avenalumin III
 35 37  0  0  0  0  0  0  0  0999 V2000
   -5.3888   -1.9416    0.3326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1698   -1.5974    0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2039   -2.4707    0.3056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9067   -2.1538    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333   -3.2336    0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3646   -3.1278    0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9831   -1.8222    0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3028   -1.7299    0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0027   -0.4793   -0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802    0.7413   -0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0986    1.9225   -0.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4665    1.9165   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1966    3.0993   -0.4940 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1097    0.6945   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3781   -0.4787   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6546   -0.8581    0.1047 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5919    0.0985    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2972    1.4370   -0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3014    2.3953   -0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6450    2.0420   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9346    0.7010    0.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9344   -0.2451    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987   -4.2796    0.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9907   -4.0333    0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4164   -0.9344    0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8597   -2.6620    0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3041    0.8210   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5763    2.8545   -0.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4859    3.5995    0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1821    0.6360   -0.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8915   -1.4334   -0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2619    1.7527   -0.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0855    3.4415   -0.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4050    2.8084   -0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9767    0.4213    0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  4 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 15  9  1  0
 22 17  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END


  Mrv0541 05061310452D          

 22 24  0  0  0  0            999 V2000
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    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
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    2.1434   -1.2375    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
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  1  1  0  0  0  0
  5  1  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13  5  1  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15  6  2  0  0  0  0
 16  7  2  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  2  0  0  0  0
 20 14  1  0  0  0  0
 21 18  2  0  0  0  0
 22 17  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038956

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(\C=C\C=C/C2=NC3=CC=CC=C3C(=O)O2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H13NO3/c20-14-11-9-13(10-12-14)5-1-4-8-17-19-16-7-3-2-6-15(16)18(21)22-17/h1-12,20H/b5-1+,8-4-

> <INCHI_KEY>
ASJBOIQMTVOWBG-UJURIKRHSA-N

> <FORMULA>
C18H13NO3

> <MOLECULAR_WEIGHT>
291.3007

> <EXACT_MASS>
291.089543287

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.935924236536824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1Z,3E)-4-(4-hydroxyphenyl)buta-1,3-dien-1-yl]-4H-3,1-benzoxazin-4-one

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
4.085683431333333

> <ALOGPS_LOGS>
-5.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.506709127746532

> <JCHEM_PKA_STRONGEST_BASIC>
1.2613956890493574

> <JCHEM_POLAR_SURFACE_AREA>
58.89

> <JCHEM_REFRACTIVITY>
88.1558

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.59e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1Z,3E)-4-(4-hydroxyphenyl)buta-1,3-dien-1-yl]-3,1-benzoxazin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038956
     RDKit          3D
Avenalumin III
 35 37  0  0  0  0  0  0  0  0999 V2000
   -5.3888   -1.9416    0.3326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1698   -1.5974    0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2039   -2.4707    0.3056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9067   -2.1538    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333   -3.2336    0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3646   -3.1278    0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9831   -1.8222    0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3028   -1.7299    0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0027   -0.4793   -0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802    0.7413   -0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0986    1.9225   -0.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4665    1.9165   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1966    3.0993   -0.4940 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1097    0.6945   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3781   -0.4787   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6546   -0.8581    0.1047 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5919    0.0985    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2972    1.4370   -0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3014    2.3953   -0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6450    2.0420   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9346    0.7010    0.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9344   -0.2451    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987   -4.2796    0.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9907   -4.0333    0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4164   -0.9344    0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8597   -2.6620    0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3041    0.8210   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5763    2.8545   -0.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4859    3.5995    0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1821    0.6360   -0.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8915   -1.4334   -0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2619    1.7527   -0.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0855    3.4415   -0.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4050    2.8084   -0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9767    0.4213    0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  4 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 15  9  1  0
 22 17  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  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       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   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       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    4    5                                                       
CONECT    2    3    6                                                       
CONECT    3    2    7                                                       
CONECT    4    1    8                                                       
CONECT    5    1   13                                                       
CONECT    6    2   15                                                       
CONECT    7    3   16                                                       
CONECT    8    4   17                                                       
CONECT    9   11   13                                                       
CONECT   10   12   13                                                       
CONECT   11    9   14                                                       
CONECT   12   10   14                                                       
CONECT   13    5    9   10                                                  
CONECT   14   11   12   20                                                  
CONECT   15    6   16   18                                                  
CONECT   16    7   15   19                                                  
CONECT   17    8   19   22                                                  
CONECT   18   15   21   22                                                  
CONECT   19   16   17                                                       
CONECT   20   14                                                            
CONECT   21   18                                                            
CONECT   22   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0038956
HETATM    1  O1  UNL     1      -5.389  -1.942   0.333  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.170  -1.597   0.259  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.204  -2.471   0.306  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.907  -2.154   0.232  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.933  -3.234   0.297  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.365  -3.128   0.242  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.983  -1.822   0.102  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.303  -1.730   0.048  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.003  -0.479  -0.091  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.380   0.741  -0.181  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.099   1.922  -0.314  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.467   1.916  -0.361  1.00  0.00           C  
HETATM   13  O3  UNL     1       5.197   3.099  -0.494  1.00  0.00           O  
HETATM   14  C11 UNL     1       5.110   0.694  -0.271  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.378  -0.479  -0.138  1.00  0.00           C  
HETATM   16  N1  UNL     1      -1.655  -0.858   0.105  1.00  0.00           N  
HETATM   17  C13 UNL     1      -2.592   0.098   0.050  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.297   1.437  -0.083  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.301   2.395  -0.136  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.645   2.042  -0.057  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.935   0.701   0.075  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.934  -0.245   0.127  1.00  0.00           C  
HETATM   23  H1  UNL     1      -1.299  -4.280   0.405  1.00  0.00           H  
HETATM   24  H2  UNL     1       0.991  -4.033   0.304  1.00  0.00           H  
HETATM   25  H3  UNL     1       0.416  -0.934   0.040  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.860  -2.662   0.114  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.304   0.821  -0.151  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.576   2.855  -0.381  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.486   3.600   0.344  1.00  0.00           H  
HETATM   30  H8  UNL     1       6.182   0.636  -0.303  1.00  0.00           H  
HETATM   31  H9  UNL     1       4.891  -1.433  -0.069  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.262   1.753  -0.148  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.085   3.441  -0.239  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.405   2.808  -0.101  1.00  0.00           H  
HETATM   35  H13 UNL     1      -5.977   0.421   0.137  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   22
CONECT    3    4
CONECT    4    5   16   16
CONECT    5    6    6   23
CONECT    6    7   24
CONECT    7    8    8   25
CONECT    8    9   26
CONECT    9   10   10   15
CONECT   10   11   27
CONECT   11   12   12   28
CONECT   12   13   14
CONECT   13   29
CONECT   14   15   15   30
CONECT   15   31
CONECT   16   17
CONECT   17   18   18   22
CONECT   18   19   32
CONECT   19   20   20   33
CONECT   20   21   34
CONECT   21   22   22   35
END

HMDB0038956
     RDKit          3D
Avenalumin III
 35 37  0  0  0  0  0  0  0  0999 V2000
   -5.3888   -1.9416    0.3326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1698   -1.5974    0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2039   -2.4707    0.3056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9067   -2.1538    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333   -3.2336    0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3646   -3.1278    0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9831   -1.8222    0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3028   -1.7299    0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0027   -0.4793   -0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802    0.7413   -0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0986    1.9225   -0.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4665    1.9165   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1966    3.0993   -0.4940 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1097    0.6945   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3781   -0.4787   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6546   -0.8581    0.1047 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5919    0.0985    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2972    1.4370   -0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3014    2.3953   -0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6450    2.0420   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9346    0.7010    0.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9344   -0.2451    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987   -4.2796    0.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9907   -4.0333    0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4164   -0.9344    0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8597   -2.6620    0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3041    0.8210   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5763    2.8545   -0.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4859    3.5995    0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1821    0.6360   -0.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8915   -1.4334   -0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2619    1.7527   -0.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0855    3.4415   -0.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4050    2.8084   -0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9767    0.4213    0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  4 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  2  1  0
 15  9  1  0
 22 17  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-[4-(4-Hydroxyphenyl)-1,3-butadienyl]-4H-3,1-benzoxazin-4-one, 9ci	HMDB

Chemical Formula

C₁₈H₁₃NO₃

Average Molecular Weight

291.3007

Monoisotopic Molecular Weight

291.089543287

IUPAC Name

2-[(1Z,3E)-4-(4-hydroxyphenyl)buta-1,3-dien-1-yl]-4H-3,1-benzoxazin-4-one

Traditional Name

2-[(1Z,3E)-4-(4-hydroxyphenyl)buta-1,3-dien-1-yl]-3,1-benzoxazin-4-one

CAS Registry Number

78214-15-0

SMILES

OC1=CC=C(\C=C\C=C/C2=NC3=CC=CC=C3C(=O)O2)C=C1

InChI Identifier

InChI=1S/C18H13NO3/c20-14-11-9-13(10-12-14)5-1-4-8-17-19-16-7-3-2-6-15(16)18(21)22-17/h1-12,20H/b5-1+,8-4-

InChI Key

ASJBOIQMTVOWBG-UJURIKRHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazines

Sub Class

Not Available

Direct Parent

Benzoxazines

Alternative Parents

Substituents

Benzoxazine
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0038956)

Cellular substructure

Membrane (HMDB: HMDB0038956)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038956)

Source

Exogenous

Food

Food (HMDB: HMDB0038956)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Oat (FooDB: FOOD00022)

Cereals and cereal products (FooDB: FOOD00858)

Endogenous

Plant

Poaceae (HMDB: HMDB0038956)

Not Available

Nutrient (HMDB: HMDB0038956)

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	0.0026 g/L	ALOGPS
logP	4.08	ALOGPS
logP	4.09	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.51	ChemAxon
pKa (Strongest Basic)	1.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	58.89 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	88.16 m³·mol⁻¹	ChemAxon
Polarizability	30.94 Å³	ChemAxon
Number of Rings	3	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]+	172.578	30932474
DeepCCS	[M-H]-	170.22	30932474
DeepCCS	[M-2H]-	204.021	30932474
DeepCCS	[M+Na]+	179.277	30932474
AllCCS	[M+H]+	168.9	32859911
AllCCS	[M+H-H2O]+	165.2	32859911
AllCCS	[M+NH4]+	172.3	32859911
AllCCS	[M+Na]+	173.3	32859911
AllCCS	[M-H]-	170.7	32859911
AllCCS	[M+Na-2H]-	169.7	32859911
AllCCS	[M+HCOO]-	168.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Avenalumin III	OC1=CC=C(\C=C\C=C/C2=NC3=CC=CC=C3C(=O)O2)C=C1	4436.3	Standard polar	33892256
Avenalumin III	OC1=CC=C(\C=C\C=C/C2=NC3=CC=CC=C3C(=O)O2)C=C1	2981.1	Standard non polar	33892256
Avenalumin III	OC1=CC=C(\C=C\C=C/C2=NC3=CC=CC=C3C(=O)O2)C=C1	3339.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Avenalumin III,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C=C\C2=NC3=CC=CC=C3C(=O)O2)C=C1	3199.6	Semi standard non polar	33892256
Avenalumin III,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C=C\C2=NC3=CC=CC=C3C(=O)O2)C=C1	3478.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Avenalumin III GC-MS (Non-derivatized) - 70eV, Positive	splash10-02mi-0890000000-3481d27ea7efc60d8ab2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Avenalumin III GC-MS (1 TMS) - 70eV, Positive	splash10-00di-6968000000-8424384b9e94e4acd8b2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Avenalumin III GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Avenalumin III 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 - Avenalumin III 10V, Positive-QTOF	splash10-0006-0290000000-6034aa8d091a9e01cfe5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenalumin III 20V, Positive-QTOF	splash10-000y-0960000000-61d491da964f95408181	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenalumin III 40V, Positive-QTOF	splash10-0zpi-3900000000-ae022f070328e0ca6ee2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenalumin III 10V, Negative-QTOF	splash10-0006-0090000000-da71ae91bfd69479a11a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenalumin III 20V, Negative-QTOF	splash10-0007-0290000000-9c404951c4c0ef53e321	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenalumin III 40V, Negative-QTOF	splash10-014l-4910000000-60766b31d04c8c4d1921	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenalumin III 10V, Positive-QTOF	splash10-0006-0090000000-d8d3847b52a192ffffa9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenalumin III 20V, Positive-QTOF	splash10-0006-0090000000-a15dab3437e437d5988f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenalumin III 40V, Positive-QTOF	splash10-0g30-1950000000-9885a8320652f821648e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenalumin III 10V, Negative-QTOF	splash10-0006-0090000000-5e6545f8266c53863c25	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenalumin III 20V, Negative-QTOF	splash10-0006-0190000000-f2838ad7bf171fd3823f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenalumin III 40V, Negative-QTOF	splash10-006x-1790000000-d0324b119d4049f76773	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB018439

KNApSAcK ID

C00054951

Chemspider ID

30777309

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

137199995

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 Avenalumin III (HMDB0038956)

MOL for HMDB0038956 (Avenalumin III)

3D MOL for HMDB0038956 (Avenalumin III)

3D SDF for HMDB0038956 (Avenalumin III)

3D-SDF for HMDB0038956 (Avenalumin III)

PDB for HMDB0038956 (Avenalumin III)

3D PDB for HMDB0038956 (Avenalumin III)

SMILES for HMDB0038956 (Avenalumin III)

INCHI for HMDB0038956 (Avenalumin III)

Structure for HMDB0038956 (Avenalumin III)

3D Structure for HMDB0038956 (Avenalumin III)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra