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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:01:56 UTC

Update Date

2022-03-07 02:53:40 UTC

HMDB ID

HMDB0033318

Secondary Accession Numbers

HMDB33318

Metabolite Identification

Common Name

Isoamericanin A

Description

Isoamericanin A belongs to the class of organic compounds known as phenylbenzo-1,4-dioxanes. These are benzo-1,3-dioxanes having a phenyl group attached to the 1,4-dioxane moiety. Isoamericanin A has been detected, but not quantified in, american pokeweeds (Phytolacca americana) and fruits. This could make isoamericanin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isoamericanin A.

Structure

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

HMDB0033318
     RDKit          3D
Isoamericanin A
 40 42  0  0  0  0  0  0  0  0999 V2000
   -6.8406    2.0045    1.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7665    1.3808    0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3257    1.7621   -0.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3207    1.2595   -1.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4478    0.2180   -0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7657   -0.7524    0.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7510   -1.6245    0.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4699   -1.5153    0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1378   -0.5379   -0.8130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1091    0.2999   -1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1767   -0.4973   -1.2563 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2703   -1.0491   -0.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2116    0.0553   -0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4596    0.9234   -1.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3145    1.9820   -1.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9577    2.2008    0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8079    3.2874    0.1086 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7236    1.3542    1.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3546    1.5616    2.2931 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8454    0.2863    0.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9055   -1.8994    0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7418   -3.1618    0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0891   -2.9103    0.7475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4556   -2.3704    0.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3958    0.6925    1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9328    2.5767   -1.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1173    1.6955   -2.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7713   -0.9126    0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0291   -2.3935    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8413    1.0721   -1.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7985   -1.7068   -1.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9850    0.8019   -2.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5100    2.6599   -2.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3406    3.5940    0.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9820    2.3373    2.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6777   -0.3606    1.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9444   -1.4040    1.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5529   -3.6909   -0.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3629   -3.8528    1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4658   -3.3659    1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 10  5  1  0
 20 13  1  0
 24  8  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
M  END

  Mrv0541 02241215502D          

 24 26  0  0  0  0            999 V2000
   -0.3574   -1.4444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    0.2047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2131    1.4430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999    0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852   -0.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706    0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852    2.2675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4999    2.2675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4999    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131    0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4999   -0.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4999   -1.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -1.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706   -1.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706   -0.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852    0.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706   -1.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706   -2.2675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  0  0  0  0
  2  3  1  0  0  0  0
  2 23  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4 21  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 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
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033318

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1OC2=CC=C(\C=C/C=O)C=C2OC1C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c19-7-1-2-11-3-6-15-16(8-11)24-18(17(10-20)23-15)12-4-5-13(21)14(22)9-12/h1-9,17-18,20-22H,10H2/b2-1-

> <INCHI_KEY>
SDDXIQONGFZHJH-UPHRSURJSA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.316

> <EXACT_MASS>
328.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
33.27290430292089

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-[3-(3,4-dihydroxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
2.037377135

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.653886057272587

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.20726426659798

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9904140632676404

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
87.29899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-[3-(3,4-dihydroxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033318
     RDKit          3D
Isoamericanin A
 40 42  0  0  0  0  0  0  0  0999 V2000
   -6.8406    2.0045    1.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7665    1.3808    0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3257    1.7621   -0.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3207    1.2595   -1.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4478    0.2180   -0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7657   -0.7524    0.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7510   -1.6245    0.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4699   -1.5153    0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1378   -0.5379   -0.8130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1091    0.2999   -1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1767   -0.4973   -1.2563 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2703   -1.0491   -0.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2116    0.0553   -0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4596    0.9234   -1.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3145    1.9820   -1.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9577    2.2008    0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8079    3.2874    0.1086 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7236    1.3542    1.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3546    1.5616    2.2931 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8454    0.2863    0.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9055   -1.8994    0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7418   -3.1618    0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0891   -2.9103    0.7475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4556   -2.3704    0.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3958    0.6925    1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9328    2.5767   -1.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1173    1.6955   -2.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7713   -0.9126    0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0291   -2.3935    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8413    1.0721   -1.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7985   -1.7068   -1.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9850    0.8019   -2.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5100    2.6599   -2.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3406    3.5940    0.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9820    2.3373    2.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6777   -0.3606    1.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9444   -1.4040    1.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5529   -3.6909   -0.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3629   -3.8528    1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4658   -3.3659    1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 10  5  1  0
 20 13  1  0
 24  8  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  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  O   UNK     0      -0.667  -2.696   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.667  -1.927   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.667  -0.387   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.667   0.382   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.998   2.694   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.666   1.924   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.666   0.382   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.332  -0.387   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.998   0.382   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.998   1.924   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.332   2.694   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.332   4.233   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -4.666   4.233   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.666   2.694   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.998   1.924   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.998   0.382   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.666  -0.387   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.666  -1.927   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.332  -2.696   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.998  -1.927   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.998  -0.387   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.332   0.382   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.998  -2.696   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.998  -4.233   0.000  0.00  0.00           O+0
CONECT    1    2   20                                                       
CONECT    2    1    3   23                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3   21                                                       
CONECT    5    6                                                            
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    3    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11    6   10   12                                                  
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20    1   19   21                                                  
CONECT   21    4   20   22                                                  
CONECT   22   17   21                                                       
CONECT   23    2   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0033318
HETATM    1  O1  UNL     1      -6.841   2.004   1.138  1.00  0.00           O  
HETATM    2  C1  UNL     1      -5.767   1.381   0.731  1.00  0.00           C  
HETATM    3  C2  UNL     1      -5.326   1.762  -0.566  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.321   1.259  -1.183  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.448   0.218  -0.728  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.766  -0.752   0.179  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.751  -1.625   0.596  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.470  -1.515   0.109  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.138  -0.538  -0.813  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.109   0.300  -1.213  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.177  -0.497  -1.256  1.00  0.00           O  
HETATM   12  C10 UNL     1       1.270  -1.049  -0.554  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.212   0.055  -0.279  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.460   0.923  -1.327  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.315   1.982  -1.188  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.958   2.201   0.036  1.00  0.00           C  
HETATM   17  O3  UNL     1       4.808   3.287   0.109  1.00  0.00           O  
HETATM   18  C15 UNL     1       3.724   1.354   1.078  1.00  0.00           C  
HETATM   19  O4  UNL     1       4.355   1.562   2.293  1.00  0.00           O  
HETATM   20  C16 UNL     1       2.845   0.286   0.898  1.00  0.00           C  
HETATM   21  C17 UNL     1       0.905  -1.899   0.602  1.00  0.00           C  
HETATM   22  C18 UNL     1       1.742  -3.162   0.659  1.00  0.00           C  
HETATM   23  O5  UNL     1       3.089  -2.910   0.748  1.00  0.00           O  
HETATM   24  O6  UNL     1      -0.456  -2.370   0.512  1.00  0.00           O  
HETATM   25  H1  UNL     1      -5.396   0.693   1.441  1.00  0.00           H  
HETATM   26  H2  UNL     1      -5.933   2.577  -1.063  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.117   1.695  -2.203  1.00  0.00           H  
HETATM   28  H4  UNL     1      -4.771  -0.913   0.531  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.029  -2.393   1.327  1.00  0.00           H  
HETATM   30  H6  UNL     1      -1.841   1.072  -1.942  1.00  0.00           H  
HETATM   31  H7  UNL     1       1.799  -1.707  -1.308  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.985   0.802  -2.307  1.00  0.00           H  
HETATM   33  H9  UNL     1       3.510   2.660  -2.002  1.00  0.00           H  
HETATM   34  H10 UNL     1       5.341   3.594   0.879  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.982   2.337   2.397  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.678  -0.361   1.719  1.00  0.00           H  
HETATM   37  H13 UNL     1       0.944  -1.404   1.594  1.00  0.00           H  
HETATM   38  H14 UNL     1       1.553  -3.691  -0.319  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.363  -3.853   1.435  1.00  0.00           H  
HETATM   40  H16 UNL     1       3.466  -3.366   1.537  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   25
CONECT    3    4    4   26
CONECT    4    5   27
CONECT    5    6    6   10
CONECT    6    7   28
CONECT    7    8    8   29
CONECT    8    9   24
CONECT    9   10   10   11
CONECT   10   30
CONECT   11   12
CONECT   12   13   21   31
CONECT   13   14   14   20
CONECT   14   15   32
CONECT   15   16   16   33
CONECT   16   17   18
CONECT   17   34
CONECT   18   19   20   20
CONECT   19   35
CONECT   20   36
CONECT   21   22   24   37
CONECT   22   23   38   39
CONECT   23   40
END

HMDB0033318
     RDKit          3D
Isoamericanin A
 40 42  0  0  0  0  0  0  0  0999 V2000
   -6.8406    2.0045    1.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7665    1.3808    0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3257    1.7621   -0.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3207    1.2595   -1.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4478    0.2180   -0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7657   -0.7524    0.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7510   -1.6245    0.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4699   -1.5153    0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1378   -0.5379   -0.8130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1091    0.2999   -1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1767   -0.4973   -1.2563 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2703   -1.0491   -0.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2116    0.0553   -0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4596    0.9234   -1.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3145    1.9820   -1.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9577    2.2008    0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8079    3.2874    0.1086 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7236    1.3542    1.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3546    1.5616    2.2931 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8454    0.2863    0.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9055   -1.8994    0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7418   -3.1618    0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0891   -2.9103    0.7475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4556   -2.3704    0.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3958    0.6925    1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9328    2.5767   -1.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1173    1.6955   -2.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7713   -0.9126    0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0291   -2.3935    1.3268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8413    1.0721   -1.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7985   -1.7068   -1.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9850    0.8019   -2.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5100    2.6599   -2.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3406    3.5940    0.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9820    2.3373    2.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6777   -0.3606    1.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9444   -1.4040    1.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5529   -3.6909   -0.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3629   -3.8528    1.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4658   -3.3659    1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 10  5  1  0
 20 13  1  0
 24  8  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isoamericanin a	MeSH

Chemical Formula

C₁₈H₁₆O₆

Average Molecular Weight

328.316

Monoisotopic Molecular Weight

328.094688244

IUPAC Name

(2Z)-3-[3-(3,4-dihydroxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal

Traditional Name

(2Z)-3-[3-(3,4-dihydroxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal

CAS Registry Number

109063-85-6

SMILES

OCC1OC2=CC=C(\C=C/C=O)C=C2OC1C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C18H16O6/c19-7-1-2-11-3-6-15-16(8-11)24-18(17(10-20)23-15)12-4-5-13(21)14(22)9-12/h1-9,17-18,20-22H,10H2/b2-1-

InChI Key

SDDXIQONGFZHJH-UPHRSURJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbenzo-1,4-dioxanes. These are benzo-1,3-dioxanes having a phenyl group attached to the 1,4-dioxane moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxanes

Sub Class

Phenylbenzodioxanes

Direct Parent

Phenylbenzo-1,4-dioxanes

Alternative Parents

Substituents

2-phenylbenzo-1,4-dioxane
Benzo-1,4-dioxane
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Para-dioxin
Benzenoid
Enal
Alpha,beta-unsaturated aldehyde
Ether
Oxacycle
Aldehyde
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Organic oxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033318)
Cell membrane (HMDB: HMDB0033318)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033318)

Source

Exogenous

Exogenous (HMDB: HMDB0033318)

Food

Food (HMDB: HMDB0033318)

Vegetable

Shoot vegetable

American pokeweed (FooDB: FOOD00437)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0033318)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033318)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	177 - 178 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5447 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.044 g/L	ALOGPS
logP	2.89	ALOGPS
logP	2.04	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	87.3 m³·mol⁻¹	ChemAxon
Polarizability	33.27 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]+	177.961	30932474
DeepCCS	[M-H]-	175.603	30932474
DeepCCS	[M-2H]-	209.416	30932474
DeepCCS	[M+Na]+	184.643	30932474
AllCCS	[M+H]+	176.5	32859911
AllCCS	[M+H-H2O]+	173.4	32859911
AllCCS	[M+NH4]+	179.4	32859911
AllCCS	[M+Na]+	180.2	32859911
AllCCS	[M-H]-	177.2	32859911
AllCCS	[M+Na-2H]-	176.7	32859911
AllCCS	[M+HCOO]-	176.3	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.	4.43 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9336 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.92 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1831.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	221.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	149.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	158.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	93.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	502.6 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	421.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	125.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	903.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	394.2 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	1215.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	290.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	299.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	346.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	164.4 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	29.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoamericanin A	OCC1OC2=CC=C(\C=C/C=O)C=C2OC1C1=CC=C(O)C(O)=C1	4324.9	Standard polar	33892256
Isoamericanin A	OCC1OC2=CC=C(\C=C/C=O)C=C2OC1C1=CC=C(O)C(O)=C1	3178.0	Standard non polar	33892256
Isoamericanin A	OCC1OC2=CC=C(\C=C/C=O)C=C2OC1C1=CC=C(O)C(O)=C1	3353.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoamericanin A,1TMS,isomer #1	C[Si](C)(C)OCC1OC2=CC=C(/C=C\C=O)C=C2OC1C1=CC=C(O)C(O)=C1	3260.7	Semi standard non polar	33892256
Isoamericanin A,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2OC3=CC(/C=C\C=O)=CC=C3OC2CO)C=C1O	3288.8	Semi standard non polar	33892256
Isoamericanin A,1TMS,isomer #3	C[Si](C)(C)OC1=CC(C2OC3=CC(/C=C\C=O)=CC=C3OC2CO)=CC=C1O	3266.9	Semi standard non polar	33892256
Isoamericanin A,2TMS,isomer #1	C[Si](C)(C)OCC1OC2=CC=C(/C=C\C=O)C=C2OC1C1=CC=C(O[Si](C)(C)C)C(O)=C1	3249.9	Semi standard non polar	33892256
Isoamericanin A,2TMS,isomer #2	C[Si](C)(C)OCC1OC2=CC=C(/C=C\C=O)C=C2OC1C1=CC=C(O)C(O[Si](C)(C)C)=C1	3233.6	Semi standard non polar	33892256
Isoamericanin A,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2OC3=CC(/C=C\C=O)=CC=C3OC2CO)C=C1O[Si](C)(C)C	3302.0	Semi standard non polar	33892256
Isoamericanin A,3TMS,isomer #1	C[Si](C)(C)OCC1OC2=CC=C(/C=C\C=O)C=C2OC1C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	3241.0	Semi standard non polar	33892256
Isoamericanin A,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC2=CC=C(/C=C\C=O)C=C2OC1C1=CC=C(O)C(O)=C1	3558.4	Semi standard non polar	33892256
Isoamericanin A,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(/C=C\C=O)=CC=C3OC2CO)C=C1O	3592.4	Semi standard non polar	33892256
Isoamericanin A,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(C2OC3=CC(/C=C\C=O)=CC=C3OC2CO)=CC=C1O	3568.9	Semi standard non polar	33892256
Isoamericanin A,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC2=CC=C(/C=C\C=O)C=C2OC1C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	3788.6	Semi standard non polar	33892256
Isoamericanin A,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC2=CC=C(/C=C\C=O)C=C2OC1C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	3763.4	Semi standard non polar	33892256
Isoamericanin A,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(/C=C\C=O)=CC=C3OC2CO)C=C1O[Si](C)(C)C(C)(C)C	3808.4	Semi standard non polar	33892256
Isoamericanin A,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC2=CC=C(/C=C\C=O)C=C2OC1C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	3943.9	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 - Isoamericanin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2693000000-66d1edc0a17c90839940	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoamericanin A GC-MS (3 TMS) - 70eV, Positive	splash10-00b9-9040680000-e5113852ae59de6281d4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoamericanin A 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 - Isoamericanin A 10V, Positive-QTOF	splash10-01t9-0639000000-bdcaed3256d2a2712124	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamericanin A 20V, Positive-QTOF	splash10-01p9-0593000000-71c518b95edab8cb6335	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamericanin A 40V, Positive-QTOF	splash10-0ac1-1900000000-91e2689548f33398fdd0	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamericanin A 10V, Negative-QTOF	splash10-004i-0009000000-b1e71a74aece0f05d985	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamericanin A 20V, Negative-QTOF	splash10-056s-1869000000-81182327e7021850590d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamericanin A 40V, Negative-QTOF	splash10-0002-1910000000-3da21e76ceff6e6fa566	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamericanin A 10V, Positive-QTOF	splash10-004i-0019000000-212b987615244dafe14c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamericanin A 20V, Positive-QTOF	splash10-02p0-0976000000-27b5b702638b80062634	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamericanin A 40V, Positive-QTOF	splash10-00dj-2961000000-0a10ad365c6299c2763e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamericanin A 10V, Negative-QTOF	splash10-004i-0049000000-b41050958a13b4d4a85c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamericanin A 20V, Negative-QTOF	splash10-014j-0591000000-ba02ccfc480397d100b1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoamericanin A 40V, Negative-QTOF	splash10-00lr-3961000000-49c8a2f7d521229ee65b	2021-09-25	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

FDB011344

KNApSAcK ID

C00031889

Chemspider ID

35013584

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751409

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1834751

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 Isoamericanin A (HMDB0033318)

MOL for HMDB0033318 (Isoamericanin A)

3D MOL for HMDB0033318 (Isoamericanin A)

3D SDF for HMDB0033318 (Isoamericanin A)

3D-SDF for HMDB0033318 (Isoamericanin A)

PDB for HMDB0033318 (Isoamericanin A)

3D PDB for HMDB0033318 (Isoamericanin A)

SMILES for HMDB0033318 (Isoamericanin A)

INCHI for HMDB0033318 (Isoamericanin A)

Structure for HMDB0033318 (Isoamericanin A)

3D Structure for HMDB0033318 (Isoamericanin A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra