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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:12:56 UTC

Update Date

2021-09-26 22:58:06 UTC

HMDB ID

HMDB0248043

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one

Description

(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one, also known as aflatoxin R, belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. Based on a literature review very few articles have been published on (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). (3s,7r)-16-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0248044
     RDKit          3D
Aflatoxicol
 37 41  0  0  0  0  0  0  0  0999 V2000
    1.0820    3.6215    1.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392    2.2984    0.8335 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1903    1.5521    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0784    2.1261    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1628    1.3690   -0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9694    0.1005   -0.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6756   -0.4478   -0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5010   -1.6492   -0.9768 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6874   -2.1961   -1.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8225   -3.3607   -1.4433 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8060   -1.5152   -0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6787   -0.2327   -0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3999    0.2816   -0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9652    0.2659    0.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8043   -0.9665    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2404   -1.9307   -0.5047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8748   -1.7425   -1.7301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665   -0.4762   -0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5587   -1.7573   -0.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3395   -1.5075    0.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6222   -0.1466    0.8802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2721    0.4913   -0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5179    1.6579   -0.1460 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549    4.1271    1.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441    4.1558    0.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5639    3.5765    2.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2967    3.1119    0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4444    0.7763   -0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0361    0.8671    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8824   -0.7977    0.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5678   -1.3515    1.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3218   -2.9539   -0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5825   -2.4351   -1.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3796   -0.5452   -2.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1980   -2.7357   -0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6962   -2.2661    1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1542    0.6350   -0.9885 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
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  6 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 13  3  1  0
 22 18  1  0
 23  5  1  0
 13  7  2  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 22 37  1  0
M  END


  Mrv0541 02241212362D          

 23 27  0  0  0  0            999 V2000
    6.9148    2.6273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0258    1.8098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3733    1.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4843    0.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2478    0.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3589   -0.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1706   -0.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5613   -0.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9910    0.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5289   -1.5329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7064   -1.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8174   -1.9651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9429   -0.8350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8319   -0.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0684    0.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3252   -0.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345   -0.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1227   -0.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0117    0.1748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7549    0.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    1.2596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9574    1.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6098    1.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  7 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  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  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248043

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2C3=C(C(O)CC3)C(=O)OC2=C2C3C=COC3OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8-9,17-18H,2-3H2,1H3

> <INCHI_KEY>
WYIWLDSPNDMZIT-UHFFFAOYSA-N

> <FORMULA>
C17H14O6

> <MOLECULAR_WEIGHT>
314.2895

> <EXACT_MASS>
314.07903818

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.945331535994015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1,4,9,11,13(17)-pentaen-18-one

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
1.0208531973333332

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.279687483824581

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1138646945751267

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
79.40740000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1,4,9,11,13(17)-pentaen-18-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248044
     RDKit          3D
Aflatoxicol
 37 41  0  0  0  0  0  0  0  0999 V2000
    1.0820    3.6215    1.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392    2.2984    0.8335 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1903    1.5521    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0784    2.1261    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1628    1.3690   -0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9694    0.1005   -0.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6756   -0.4478   -0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5010   -1.6492   -0.9768 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6874   -2.1961   -1.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8225   -3.3607   -1.4433 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8060   -1.5152   -0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6787   -0.2327   -0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3999    0.2816   -0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9652    0.2659    0.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8043   -0.9665    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2404   -1.9307   -0.5047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8748   -1.7425   -1.7301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665   -0.4762   -0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5587   -1.7573   -0.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3395   -1.5075    0.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6222   -0.1466    0.8802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2721    0.4913   -0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5179    1.6579   -0.1460 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549    4.1271    1.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441    4.1558    0.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5639    3.5765    2.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2967    3.1119    0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4444    0.7763   -0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0361    0.8671    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8824   -0.7977    0.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5678   -1.3515    1.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3218   -2.9539   -0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5825   -2.4351   -1.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3796   -0.5452   -2.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1980   -2.7357   -0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6962   -2.2661    1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1542    0.6350   -0.9885 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
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  6 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 13  3  1  0
 22 18  1  0
 23  5  1  0
 13  7  2  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 22 37  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      12.908   4.904   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      13.115   3.378   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.897   2.436   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.104   0.910   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.529   0.326   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.737  -1.200   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.252  -1.474   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.981  -0.118   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.917   0.995   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      15.921  -2.861   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.519  -2.142   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.726  -3.668   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      11.093  -1.559   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.886  -0.033   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.461   0.551   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.074  -0.118   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.344  -1.474   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.829  -1.200   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.622   0.326   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.009   0.995   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.738   2.351   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.254   2.077   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.472   3.019   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    7                                                            
CONECT   11    6   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    4   15                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   15   23                                                  
CONECT   23   22    3                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0248043
HETATM    1  C1  UNL     1      -1.370   3.716   0.549  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.421   2.322   0.321  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.326   1.551   0.063  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.945   2.132   0.013  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.041   1.317  -0.253  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.890  -0.039  -0.463  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.630  -0.598  -0.410  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.459  -1.886  -0.607  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.714  -2.463  -0.567  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.859  -3.695  -0.757  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.846  -1.686  -0.303  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.752  -0.332  -0.087  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.486   0.202  -0.145  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.071   0.207   0.155  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.900  -0.989   0.571  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.271  -2.129  -0.208  1.00  0.00           C  
HETATM   17  O4  UNL     1      -3.424  -3.288   0.513  1.00  0.00           O  
HETATM   18  C14 UNL     1       3.216  -0.622  -0.716  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.837  -1.216   0.467  1.00  0.00           C  
HETATM   20  C16 UNL     1       5.047  -0.702   0.609  1.00  0.00           C  
HETATM   21  O5  UNL     1       5.302   0.222  -0.414  1.00  0.00           O  
HETATM   22  C17 UNL     1       4.076   0.575  -1.020  1.00  0.00           C  
HETATM   23  O6  UNL     1       3.408   1.616  -0.362  1.00  0.00           O  
HETATM   24  H1  UNL     1      -2.415   4.122   0.427  1.00  0.00           H  
HETATM   25  H2  UNL     1      -0.689   4.157  -0.191  1.00  0.00           H  
HETATM   26  H3  UNL     1      -1.053   3.945   1.605  1.00  0.00           H  
HETATM   27  H4  UNL     1       1.063   3.176   0.174  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.544   0.600  -0.768  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.147   0.917   1.003  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.777  -1.194   1.664  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.974  -0.868   0.354  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.748  -2.156  -1.187  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.722  -3.469   1.163  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.236  -1.288  -1.608  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.425  -1.956   1.148  1.00  0.00           H  
HETATM   36  H13 UNL     1       5.783  -0.914   1.374  1.00  0.00           H  
HETATM   37  H14 UNL     1       4.150   0.713  -2.106  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   27
CONECT    5    6    6   23
CONECT    6    7   18
CONECT    7    8   13   13
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   16
CONECT   12   13   14
CONECT   14   15   28   29
CONECT   15   16   30   31
CONECT   16   17   32
CONECT   17   33
CONECT   18   19   22   34
CONECT   19   20   20   35
CONECT   20   21   36
CONECT   21   22
CONECT   22   23   37
END

HMDB0248044
     RDKit          3D
Aflatoxicol
 37 41  0  0  0  0  0  0  0  0999 V2000
    1.0820    3.6215    1.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392    2.2984    0.8335 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1903    1.5521    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0784    2.1261    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1628    1.3690   -0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9694    0.1005   -0.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6756   -0.4478   -0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5010   -1.6492   -0.9768 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6874   -2.1961   -1.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8225   -3.3607   -1.4433 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8060   -1.5152   -0.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6787   -0.2327   -0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3999    0.2816   -0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9652    0.2659    0.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8043   -0.9665    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2404   -1.9307   -0.5047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8748   -1.7425   -1.7301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665   -0.4762   -0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5587   -1.7573   -0.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3395   -1.5075    0.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6222   -0.1466    0.8802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2721    0.4913   -0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5179    1.6579   -0.1460 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549    4.1271    1.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441    4.1558    0.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5639    3.5765    2.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2967    3.1119    0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4444    0.7763   -0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0361    0.8671    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8824   -0.7977    0.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5678   -1.3515    1.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3218   -2.9539   -0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5825   -2.4351   -1.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3796   -0.5452   -2.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1980   -2.7357   -0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6962   -2.2661    1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1542    0.6350   -0.9885 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
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  6 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 13  3  1  0
 22 18  1  0
 23  5  1  0
 13  7  2  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 22 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Aflatoxicol, (1R-(1alpha,6aalpha,9aalpha))-isomer	HMDB
Aflatoxin R	HMDB

Chemical Formula

C₁₇H₁₄O₆

Average Molecular Weight

314.2895

Monoisotopic Molecular Weight

314.07903818

IUPAC Name

16-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1,4,9,11,13(17)-pentaen-18-one

Traditional Name

16-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1,4,9,11,13(17)-pentaen-18-one

CAS Registry Number

Not Available

SMILES

COC1=C2C3=C(C(O)CC3)C(=O)OC2=C2C3C=COC3OC2=C1

InChI Identifier

InChI=1S/C17H14O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8-9,17-18H,2-3H2,1H3

InChI Key

WYIWLDSPNDMZIT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Angular furanocoumarins

Alternative Parents

Substituents

Angular furanocoumarin
Benzopyran
1-benzopyran
Coumaran
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Dihydrofuran
Secondary alcohol
Lactone
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

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
logP	1.19	ALOGPS
logP	1.02	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.28	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.41 m³·mol⁻¹	ChemAxon
Polarizability	30.95 Å³	ChemAxon
Number of Rings	5	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]+	172.575	30932474
DeepCCS	[M-H]-	170.217	30932474
DeepCCS	[M-2H]-	203.756	30932474
DeepCCS	[M+Na]+	178.983	30932474
AllCCS	[M+H]+	171.2	32859911
AllCCS	[M+H-H2O]+	168.0	32859911
AllCCS	[M+NH4]+	174.2	32859911
AllCCS	[M+Na]+	175.0	32859911
AllCCS	[M-H]-	172.2	32859911
AllCCS	[M+Na-2H]-	171.3	32859911
AllCCS	[M+HCOO]-	170.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	12.5823 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.62 minutes	32390414

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C)CC1)C1C=COC1O2	2945.1	Semi standard non polar	33892256
(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C)CC1)C1C=COC1O2	2811.1	Standard non polar	33892256
(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C)CC1)C1C=COC1O2	4009.7	Standard polar	33892256
(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TBDMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C(C)(C)C)CC1)C1C=COC1O2	3170.7	Semi standard non polar	33892256
(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TBDMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C(C)(C)C)CC1)C1C=COC1O2	3050.6	Standard non polar	33892256
(3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one,1TBDMS,isomer #1	COC1=CC2=C(C3=C1C1=C(C(=O)O3)C(O[Si](C)(C)C(C)(C)C)CC1)C1C=COC1O2	4064.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ds-0090000000-3383a3871ef632b3b597	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 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 - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 10V, Positive-QTOF	splash10-00kb-0095000000-71c58c811fa86c4f350f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 20V, Positive-QTOF	splash10-00kb-0092000000-25d664ddf6f71729d9c9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 40V, Positive-QTOF	splash10-07xs-2390000000-d8e7c756bedcdafe8d00	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 10V, Negative-QTOF	splash10-03di-0059000000-7536a2ca78d64e601ad7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 20V, Negative-QTOF	splash10-03dj-0094000000-bdac8584ca3c38da05b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 40V, Negative-QTOF	splash10-0gb9-3190000000-f6139c8985207a374eaa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 10V, Negative-QTOF	splash10-03di-0009000000-7c7169b7540bc9455826	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 20V, Negative-QTOF	splash10-03di-0039000000-cf442be2c6395255469f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 40V, Negative-QTOF	splash10-03xs-0292000000-729af1d7e1ce8cc5d258	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 10V, Positive-QTOF	splash10-014i-0029000000-c8d393f9a78874956ee0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 20V, Positive-QTOF	splash10-014i-0029000000-c8d393f9a78874956ee0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one 40V, Positive-QTOF	splash10-0a4i-0090000000-6efb3590dae7ff13062b	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

546073

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

628754

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one (HMDB0248043)

MOL for HMDB0248043 ((3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one)

3D MOL for HMDB0248043 ((3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one)

3D SDF for HMDB0248043 ((3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one)

3D-SDF for HMDB0248043 ((3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one)

PDB for HMDB0248043 ((3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one)

3D PDB for HMDB0248043 ((3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one)

SMILES for HMDB0248043 ((3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one)

INCHI for HMDB0248043 ((3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one)

Structure for HMDB0248043 ((3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one)

3D Structure for HMDB0248043 ((3S,7R)-16-Hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra