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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 18:10:10 UTC

Update Date

2022-09-22 18:34:25 UTC

HMDB ID

HMDB0033435

Secondary Accession Numbers

HMDB33435

Metabolite Identification

Common Name

(±)-Aegeline

Description

(±)-Aegeline, also known as aegeline, belongs to the class of organic compounds known as cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid (±)-Aegeline has been detected, but not quantified in, fruits. This could make (±)-aegeline a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (±)-Aegeline.

Structure

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

HMDB0033435
     RDKit          3D
(±)-Aegeline
 41 42  0  0  0  0  0  0  0  0999 V2000
   -7.8768    0.3109    0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0003    0.1531   -0.9557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6326   -0.0407   -0.7905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1255   -0.0778    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7557   -0.2722    0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9301   -0.4229   -0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4824   -0.6269   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0165   -1.6703   -1.0574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6685    0.5813   -0.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487    0.4266   -0.3700 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3357    0.1452    0.8695 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5704    0.0240    1.8615 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7611   -0.0174    1.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6502    0.0870    0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0597   -0.0763    0.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9322    0.0488   -0.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2742   -0.0926   -0.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7794   -0.3688    0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9577   -0.5045    1.8111 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5725   -0.3504    1.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4717   -0.3801   -1.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8418   -0.1870   -1.9109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4540    1.0326    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8284    0.7675   -0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0823   -0.6384    0.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7426    0.0366    1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3175   -0.3081    1.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2415   -0.9386    0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6974   -1.9551   -1.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0032    1.4673    0.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8697    0.8187   -1.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786    0.5313   -1.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1154   -0.2347    2.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3081    0.3088   -0.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5567    0.2670   -1.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9715    0.0027   -1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8465   -0.4928    0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3381   -0.7176    2.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9704   -0.4659    2.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8456   -0.4955   -2.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2431   -0.1572   -2.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21 22  2  0
 22  3  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
M  END


  Mrv0541 02241208252D          

 22 23  0  0  0  0            999 V2000
   -3.2151   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6441   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 15  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033435

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C=C1)C(O)CNC(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO3/c1-22-16-10-8-15(9-11-16)17(20)13-19-18(21)12-7-14-5-3-2-4-6-14/h2-12,17,20H,13H2,1H3,(H,19,21)/b12-7+

> <INCHI_KEY>
QRFDENJATPJOKG-KPKJPENVSA-N

> <FORMULA>
C18H19NO3

> <MOLECULAR_WEIGHT>
297.3484

> <EXACT_MASS>
297.136493479

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.93848098462312

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenylprop-2-enamide

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.4892866216666674

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.802109999059446

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.091318957998404

> <JCHEM_PKA_STRONGEST_BASIC>
1.108336137606204

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
86.81710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenylprop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033435
     RDKit          3D
(±)-Aegeline
 41 42  0  0  0  0  0  0  0  0999 V2000
   -7.8768    0.3109    0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0003    0.1531   -0.9557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6326   -0.0407   -0.7905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1255   -0.0778    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7557   -0.2722    0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9301   -0.4229   -0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4824   -0.6269   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0165   -1.6703   -1.0574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6685    0.5813   -0.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487    0.4266   -0.3700 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3357    0.1452    0.8695 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5704    0.0240    1.8615 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7611   -0.0174    1.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6502    0.0870    0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0597   -0.0763    0.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9322    0.0488   -0.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2742   -0.0926   -0.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7794   -0.3688    0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9577   -0.5045    1.8111 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5725   -0.3504    1.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4717   -0.3801   -1.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8418   -0.1870   -1.9109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4540    1.0326    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8284    0.7675   -0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0823   -0.6384    0.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7426    0.0366    1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3175   -0.3081    1.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2415   -0.9386    0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6974   -1.9551   -1.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0032    1.4673    0.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8697    0.8187   -1.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786    0.5313   -1.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1154   -0.2347    2.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3081    0.3088   -0.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5567    0.2670   -1.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9715    0.0027   -1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8465   -0.4928    0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3381   -0.7176    2.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9704   -0.4659    2.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8456   -0.4955   -2.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2431   -0.1572   -2.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21 22  2  0
 22  3  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.002  -0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.002  -1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.668  -2.695   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.334  -1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.334  -0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.668   0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.001   0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.001   1.925   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       0.667   0.385   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.001  -0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.334   0.385   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.001  -1.925   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.668  -0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.002   0.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.335  -0.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.669   0.385   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.669   1.925   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.335   2.695   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.002   1.925   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -7.335  -2.695   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.669  -1.925   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7   10                                                       
CONECT    9    7                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   14                                                       
CONECT   13   11                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21    2   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0033435
HETATM    1  C1  UNL     1      -7.877   0.311   0.131  1.00  0.00           C  
HETATM    2  O1  UNL     1      -7.000   0.153  -0.956  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.633  -0.041  -0.791  1.00  0.00           C  
HETATM    4  C3  UNL     1      -5.126  -0.078   0.498  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.756  -0.272   0.647  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.930  -0.423  -0.446  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.482  -0.627  -0.222  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.016  -1.670  -1.057  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.668   0.581  -0.569  1.00  0.00           C  
HETATM   10  N1  UNL     1       0.749   0.427  -0.370  1.00  0.00           N  
HETATM   11  C8  UNL     1       1.336   0.145   0.870  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.570   0.024   1.862  1.00  0.00           O  
HETATM   13  C9  UNL     1       2.761  -0.017   1.097  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.650   0.087   0.139  1.00  0.00           C  
HETATM   15  C11 UNL     1       5.060  -0.076   0.377  1.00  0.00           C  
HETATM   16  C12 UNL     1       5.932   0.049  -0.684  1.00  0.00           C  
HETATM   17  C13 UNL     1       7.274  -0.093  -0.533  1.00  0.00           C  
HETATM   18  C14 UNL     1       7.779  -0.369   0.716  1.00  0.00           C  
HETATM   19  C15 UNL     1       6.958  -0.505   1.811  1.00  0.00           C  
HETATM   20  C16 UNL     1       5.572  -0.350   1.611  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.472  -0.380  -1.713  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.842  -0.187  -1.911  1.00  0.00           C  
HETATM   23  H1  UNL     1      -7.454   1.033   0.890  1.00  0.00           H  
HETATM   24  H2  UNL     1      -8.828   0.768  -0.195  1.00  0.00           H  
HETATM   25  H3  UNL     1      -8.082  -0.638   0.669  1.00  0.00           H  
HETATM   26  H4  UNL     1      -5.743   0.037   1.380  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.318  -0.308   1.627  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.241  -0.939   0.797  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.697  -1.955  -1.689  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.003   1.467   0.006  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.870   0.819  -1.632  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.379   0.531  -1.205  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.115  -0.235   2.099  1.00  0.00           H  
HETATM   34  H12 UNL     1       3.308   0.309  -0.893  1.00  0.00           H  
HETATM   35  H13 UNL     1       5.557   0.267  -1.681  1.00  0.00           H  
HETATM   36  H14 UNL     1       7.972   0.003  -1.356  1.00  0.00           H  
HETATM   37  H15 UNL     1       8.847  -0.493   0.898  1.00  0.00           H  
HETATM   38  H16 UNL     1       7.338  -0.718   2.779  1.00  0.00           H  
HETATM   39  H17 UNL     1       4.970  -0.466   2.499  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.846  -0.496  -2.583  1.00  0.00           H  
HETATM   41  H19 UNL     1      -5.243  -0.157  -2.916  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7   21
CONECT    7    8    9   28
CONECT    8   29
CONECT    9   10   30   31
CONECT   10   11   32
CONECT   11   12   12   13
CONECT   13   14   14   33
CONECT   14   15   34
CONECT   15   16   16   20
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   18   19   37
CONECT   19   20   20   38
CONECT   20   39
CONECT   21   22   22   40
CONECT   22   41
END

HMDB0033435
     RDKit          3D
(±)-Aegeline
 41 42  0  0  0  0  0  0  0  0999 V2000
   -7.8768    0.3109    0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0003    0.1531   -0.9557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6326   -0.0407   -0.7905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1255   -0.0778    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7557   -0.2722    0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9301   -0.4229   -0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4824   -0.6269   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0165   -1.6703   -1.0574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6685    0.5813   -0.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487    0.4266   -0.3700 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3357    0.1452    0.8695 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5704    0.0240    1.8615 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7611   -0.0174    1.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6502    0.0870    0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0597   -0.0763    0.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9322    0.0488   -0.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2742   -0.0926   -0.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7794   -0.3688    0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9577   -0.5045    1.8111 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5725   -0.3504    1.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4717   -0.3801   -1.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8418   -0.1870   -1.9109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4540    1.0326    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8284    0.7675   -0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0823   -0.6384    0.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7426    0.0366    1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3175   -0.3081    1.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2415   -0.9386    0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6974   -1.9551   -1.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0032    1.4673    0.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8697    0.8187   -1.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786    0.5313   -1.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1154   -0.2347    2.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3081    0.3088   -0.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5567    0.2670   -1.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9715    0.0027   -1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8465   -0.4928    0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3381   -0.7176    2.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9704   -0.4659    2.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8456   -0.4955   -2.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2431   -0.1572   -2.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21 22  2  0
 22  3  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Aegeline	HMDB
N-(2-Hydroxy-2(4-methoxyphenyl)ethyl)-3-phenyl-2-propenamide	HMDB
(2E)-N-[2-Hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenylprop-2-enimidate	HMDB

Chemical Formula

C₁₈H₁₉NO₃

Average Molecular Weight

297.3484

Monoisotopic Molecular Weight

297.136493479

IUPAC Name

(2E)-N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenylprop-2-enamide

Traditional Name

(2E)-N-[2-hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenylprop-2-enamide

CAS Registry Number

37791-13-2

SMILES

COC1=CC=C(C=C1)C(O)CNC(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H19NO3/c1-22-16-10-8-15(9-11-16)17(20)13-19-18(21)12-7-14-5-3-2-4-6-14/h2-12,17,20H,13H2,1H3,(H,19,21)/b12-7+

InChI Key

QRFDENJATPJOKG-KPKJPENVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid amides

Direct Parent

Cinnamic acid amides

Alternative Parents

Substituents

Cinnamic acid amide
Anisole
Phenol ether
Styrene
Methoxybenzene
Phenoxy compound
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Ether
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033435)
Cytoplasm (HMDB: HMDB0033435)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033435)

Source

Exogenous

Exogenous (HMDB: HMDB0033435)

Food

Food (HMDB: HMDB0033435)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0033435)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033435)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	176 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	2.48	ALOGPS
logP	2.49	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	1.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	86.82 m³·mol⁻¹	ChemAxon
Polarizability	32.94 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]+	169.845	30932474
DeepCCS	[M-H]-	167.487	30932474
DeepCCS	[M-2H]-	200.893	30932474
DeepCCS	[M+Na]+	176.12	30932474
AllCCS	[M+H]+	172.9	32859911
AllCCS	[M+H-H2O]+	169.5	32859911
AllCCS	[M+NH4]+	176.2	32859911
AllCCS	[M+Na]+	177.1	32859911
AllCCS	[M-H]-	175.1	32859911
AllCCS	[M+Na-2H]-	175.0	32859911
AllCCS	[M+HCOO]-	175.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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. Predicted by Afia on May 17, 2022.	6.97 minutes	32390414
Predicted by Siyang on May 30, 2022	13.3854 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.16 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2348.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	330.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	186.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	190.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	155.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	510.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	600.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	88.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1229.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	475.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1373.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	342.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	379.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	279.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	158.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-Aegeline	COC1=CC=C(C=C1)C(O)CNC(=O)\C=C\C1=CC=CC=C1	3955.8	Standard polar	33892256
(??)-Aegeline	COC1=CC=C(C=C1)C(O)CNC(=O)\C=C\C1=CC=CC=C1	2478.5	Standard non polar	33892256
(??)-Aegeline	COC1=CC=C(C=C1)C(O)CNC(=O)\C=C\C1=CC=CC=C1	2988.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(??)-Aegeline,1TMS,isomer #1	COC1=CC=C(C(CNC(=O)/C=C/C2=CC=CC=C2)O[Si](C)(C)C)C=C1	2841.9	Semi standard non polar	33892256
(??)-Aegeline,1TMS,isomer #2	COC1=CC=C(C(O)CN(C(=O)/C=C/C2=CC=CC=C2)[Si](C)(C)C)C=C1	2829.6	Semi standard non polar	33892256
(±)-Aegeline,2TMS,isomer #1	COC1=CC=C(C(CN(C(=O)/C=C/C2=CC=CC=C2)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2791.3	Semi standard non polar	33892256
(±)-Aegeline,2TMS,isomer #1	COC1=CC=C(C(CN(C(=O)/C=C/C2=CC=CC=C2)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2549.3	Standard non polar	33892256
(??)-Aegeline,1TBDMS,isomer #1	COC1=CC=C(C(CNC(=O)/C=C/C2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)C=C1	3109.4	Semi standard non polar	33892256
(??)-Aegeline,1TBDMS,isomer #2	COC1=CC=C(C(O)CN(C(=O)/C=C/C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1	3068.3	Semi standard non polar	33892256
(±)-Aegeline,2TBDMS,isomer #1	COC1=CC=C(C(CN(C(=O)/C=C/C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	3254.9	Semi standard non polar	33892256
(±)-Aegeline,2TBDMS,isomer #1	COC1=CC=C(C(CN(C(=O)/C=C/C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	2991.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Aegeline GC-MS (Non-derivatized) - 70eV, Positive	splash10-001r-1910000000-633878445dce08738375	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Aegeline GC-MS (1 TMS) - 70eV, Positive	splash10-0ff0-5931000000-c6c10b6edd7272ffa2ab	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Aegeline 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-Aegeline , positive-QTOF	splash10-0f89-0900000000-4d557981266b31d04b42	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (±)-Aegeline , positive-QTOF	splash10-0ue9-0900000000-0b319c3793f21b0b4423	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Aegeline 10V, Positive-QTOF	splash10-00ls-0970000000-836f8f28f565fd62efd2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Aegeline 20V, Positive-QTOF	splash10-00l2-0910000000-de537485ed72ae9f3dae	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Aegeline 40V, Positive-QTOF	splash10-0f7t-0900000000-8eee608fa7e5e4688195	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Aegeline 10V, Negative-QTOF	splash10-0002-0390000000-42b16adcb965e754fb7f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Aegeline 20V, Negative-QTOF	splash10-002b-1950000000-e25d0adca22cf688ec38	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Aegeline 40V, Negative-QTOF	splash10-0006-5900000000-6397133471ec8dfe82c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Aegeline 10V, Negative-QTOF	splash10-0002-0190000000-872a22a5097454ff3493	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Aegeline 20V, Negative-QTOF	splash10-0f97-4950000000-e7d04767984589f291c6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Aegeline 40V, Negative-QTOF	splash10-0w4l-7950000000-1f2cb789088ad05307cb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Aegeline 10V, Positive-QTOF	splash10-001i-0920000000-5c98a88f3b31cf384ee7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Aegeline 20V, Positive-QTOF	splash10-0udi-0900000000-34f40e51b77000b52256	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Aegeline 40V, Positive-QTOF	splash10-0udi-1900000000-a61e2784575df8e72ca7	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB011473

KNApSAcK ID

Not Available

Chemspider ID

10296259

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15558419

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 (±)-Aegeline (HMDB0033435)

MOL for HMDB0033435 ((±)-Aegeline)

3D MOL for HMDB0033435 ((±)-Aegeline)

3D SDF for HMDB0033435 ((±)-Aegeline)

3D-SDF for HMDB0033435 ((±)-Aegeline)

PDB for HMDB0033435 ((±)-Aegeline)

3D PDB for HMDB0033435 ((±)-Aegeline)

SMILES for HMDB0033435 ((±)-Aegeline)

INCHI for HMDB0033435 ((±)-Aegeline)

Structure for HMDB0033435 ((±)-Aegeline)

3D Structure for HMDB0033435 ((±)-Aegeline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra