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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 02:01:42 UTC

Update Date

2021-09-26 22:58:57 UTC

HMDB ID

HMDB0248599

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Aristolochic acid B

Description

Aristolochic acid B, also known as aristolochate b, belongs to the class of organic compounds known as aristolochic acids and derivatives. These are organic heterocyclic compounds with a structure characterized by a nitrophenanthro[3,4-d][1,3]dioxole ring system substituted at position 5, 6, and 8 by a carboxyl group (or a derivative thereof), a nitro group, and a methoxy group, respectively. Based on a literature review a significant number of articles have been published on Aristolochic acid B. This compound has been identified in human blood as reported by (PMID: 31557052 ). Aristolochic acid b is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Aristolochic acid B 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

HMDB0248599
     RDKit          3D
Aristolochic acid B
 32 35  0  0  0  0  0  0  0  0999 V2000
    3.4258   -1.4576    1.0207 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4268   -0.7314   -0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4923   -0.7177   -0.8757 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1841    0.0417   -0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3448    1.4269   -0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815    2.2705   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0145    1.7895   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1646    0.4214   -0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9262   -0.4715   -0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7427   -1.8281   -0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6985   -2.8344   -0.2496 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.5084   -2.8158   -1.1668 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6326   -3.9951    0.4909 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.5564   -2.3531    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009   -1.4865    0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8760   -2.0505    0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9429   -1.1845    0.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7906    0.1746    0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5160    0.7389    0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4379   -0.1169    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7852    2.9096   -0.0568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0211    4.0864    0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2634    3.6830   -0.2801 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4967   -1.0301   -1.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3588    1.7876   -0.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -3.4358    0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0028   -3.1318    0.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391   -1.6030    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6092    0.8873    0.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137    1.7958    0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517    4.3136    1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3455    4.9170   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 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
  7 21  1  0
 21 22  1  0
 22 23  1  0
  9  4  1  0
 20 15  1  0
 23  6  1  0
 20  8  1  0
  3 24  1  0
  5 25  1  0
 14 26  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
 22 31  1  0
 22 32  1  0
M  CHG  2  11   1  13  -1
M  END

  Mrv1533004241508492D          

 23 26  0  0  0  0            999 V2000
   -0.7857   -5.2288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0531   -4.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6418   -5.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0155   -4.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105   -3.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6729   -2.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2601   -2.1770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8906   -1.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0749   -1.5629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0597   -2.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7546   -2.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4871   -2.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5247   -1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2573   -1.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9522   -1.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9146   -2.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1821   -2.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445   -3.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4119   -4.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7170   -3.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3743   -4.9144    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.0048   -5.6520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0692   -5.3591    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  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
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  4 20  2  0  0  0  0
 11 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  CHG  2  21   1  23  -1
M  END
> <DATABASE_ID>
HMDB0248599

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=C2C(=CC3=CC=CC=C3C2=C2OCOC2=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H9NO6/c18-16(19)10-6-12-15(23-7-22-12)14-9-4-2-1-3-8(9)5-11(13(10)14)17(20)21/h1-6H,7H2,(H,18,19)

> <INCHI_KEY>
MEEXETVZNQYRSP-UHFFFAOYSA-N

> <FORMULA>
C16H9NO6

> <MOLECULAR_WEIGHT>
311.249

> <EXACT_MASS>
311.042987014

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
29.269654858368018

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-nitro-14,16-dioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylic acid

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
3.1729998943333326

> <ALOGPS_LOGS>
-3.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1532842309843785

> <JCHEM_PKA_STRONGEST_BASIC>
-4.773598551393984

> <JCHEM_POLAR_SURFACE_AREA>
98.9

> <JCHEM_REFRACTIVITY>
78.30199999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aristolochic acid II

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248599
     RDKit          3D
Aristolochic acid B
 32 35  0  0  0  0  0  0  0  0999 V2000
    3.4258   -1.4576    1.0207 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4268   -0.7314   -0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4923   -0.7177   -0.8757 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1841    0.0417   -0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3448    1.4269   -0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815    2.2705   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0145    1.7895   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1646    0.4214   -0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9262   -0.4715   -0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7427   -1.8281   -0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6985   -2.8344   -0.2496 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.5084   -2.8158   -1.1668 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6326   -3.9951    0.4909 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.5564   -2.3531    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009   -1.4865    0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8760   -2.0505    0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9429   -1.1845    0.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7906    0.1746    0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5160    0.7389    0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4379   -0.1169    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7852    2.9096   -0.0568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0211    4.0864    0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2634    3.6830   -0.2801 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4967   -1.0301   -1.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3588    1.7876   -0.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -3.4358    0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0028   -3.1318    0.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391   -1.6030    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6092    0.8873    0.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137    1.7958    0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517    4.3136    1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3455    4.9170   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 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
  7 21  1  0
 21 22  1  0
 22 23  1  0
  9  4  1  0
 20 15  1  0
 23  6  1  0
 20  8  1  0
  3 24  1  0
  5 25  1  0
 14 26  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
 22 31  1  0
 22 32  1  0
M  CHG  2  11   1  13  -1
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0      -1.467  -9.760   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.099  -9.052   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.198  -9.882   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.029  -7.514   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.326  -6.684   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.256  -5.145   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.352  -4.064   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.662  -2.687   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.140  -2.917   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.111  -4.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.409  -5.267   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.776  -4.558   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.846  -3.020   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.214  -2.312   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.511  -3.142   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.441  -4.680   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.073  -5.388   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.003  -6.927   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.636  -7.635   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.338  -6.805   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       2.565  -9.174   0.000  0.00  0.00           N+1
HETATM   22  O   UNK     0       1.876 -10.550   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.863 -10.004   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19    4   11                                                  
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0248599
HETATM    1  O1  UNL     1       3.426  -1.458   1.021  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.427  -0.731  -0.044  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.492  -0.718  -0.876  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.184   0.042  -0.242  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.345   1.427  -0.309  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.281   2.271  -0.234  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.014   1.789  -0.092  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.165   0.421  -0.033  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.926  -0.472  -0.112  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.743  -1.828  -0.050  1.00  0.00           C  
HETATM   11  N1  UNL     1       1.699  -2.834  -0.250  1.00  0.00           N1+
HETATM   12  O3  UNL     1       2.508  -2.816  -1.167  1.00  0.00           O  
HETATM   13  O4  UNL     1       1.633  -3.995   0.491  1.00  0.00           O1-
HETATM   14  C9  UNL     1      -0.556  -2.353   0.117  1.00  0.00           C  
HETATM   15  C10 UNL     1      -1.601  -1.486   0.200  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.876  -2.050   0.367  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.943  -1.185   0.454  1.00  0.00           C  
HETATM   18  C13 UNL     1      -3.791   0.175   0.379  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.516   0.739   0.212  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.438  -0.117   0.127  1.00  0.00           C  
HETATM   21  O5  UNL     1      -0.785   2.910  -0.057  1.00  0.00           O  
HETATM   22  C16 UNL     1      -0.021   4.086   0.138  1.00  0.00           C  
HETATM   23  O6  UNL     1       1.263   3.683  -0.280  1.00  0.00           O  
HETATM   24  H1  UNL     1       4.497  -1.030  -1.843  1.00  0.00           H  
HETATM   25  H2  UNL     1       3.359   1.788  -0.426  1.00  0.00           H  
HETATM   26  H3  UNL     1      -0.714  -3.436   0.177  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.003  -3.132   0.427  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.939  -1.603   0.580  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.609   0.887   0.441  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.414   1.796   0.162  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.052   4.314   1.228  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.345   4.917  -0.508  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   24
CONECT    4    5    5    9
CONECT    5    6   25
CONECT    6    7    7   23
CONECT    7    8   21
CONECT    8    9    9   20
CONECT    9   10
CONECT   10   11   14   14
CONECT   11   12   12   13
CONECT   14   15   26
CONECT   15   16   16   20
CONECT   16   17   27
CONECT   17   18   18   28
CONECT   18   19   29
CONECT   19   20   20   30
CONECT   21   22
CONECT   22   23   31   32
END

HMDB0248599
     RDKit          3D
Aristolochic acid B
 32 35  0  0  0  0  0  0  0  0999 V2000
    3.4258   -1.4576    1.0207 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4268   -0.7314   -0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4923   -0.7177   -0.8757 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1841    0.0417   -0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3448    1.4269   -0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815    2.2705   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0145    1.7895   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1646    0.4214   -0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9262   -0.4715   -0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7427   -1.8281   -0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6985   -2.8344   -0.2496 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.5084   -2.8158   -1.1668 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6326   -3.9951    0.4909 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.5564   -2.3531    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009   -1.4865    0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8760   -2.0505    0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9429   -1.1845    0.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7906    0.1746    0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5160    0.7389    0.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4379   -0.1169    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7852    2.9096   -0.0568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0211    4.0864    0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2634    3.6830   -0.2801 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4967   -1.0301   -1.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3588    1.7876   -0.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -3.4358    0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0028   -3.1318    0.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391   -1.6030    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6092    0.8873    0.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137    1.7958    0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517    4.3136    1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3455    4.9170   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 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
  7 21  1  0
 21 22  1  0
 22 23  1  0
  9  4  1  0
 20 15  1  0
 23  6  1  0
 20  8  1  0
  3 24  1  0
  5 25  1  0
 14 26  1  0
 16 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
 22 31  1  0
 22 32  1  0
M  CHG  2  11   1  13  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Aristolochate b	Generator
Aristolochate II	Generator
Aristolochic acid b	MeSH
6-Nitrophenanthro(3,4-D)-3-dioxole-5-carboxylic acid	MeSH
9-Nitro-14,16-dioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(10),2,4,6,8,11,13(17)-heptaene-11-carboxylate	Generator
9-Nitro-14,16-dioxatetracyclo[8.7.0.0,.0,]heptadeca-1(10),2,4,6,8,11,13(17)-heptaene-11-carboxylate	Generator

Chemical Formula

C₁₆H₉NO₆

Average Molecular Weight

311.249

Monoisotopic Molecular Weight

311.042987014

IUPAC Name

9-nitro-14,16-dioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylic acid

Traditional Name

aristolochic acid II

CAS Registry Number

Not Available

SMILES

OC(=O)C1=C2C(=CC3=CC=CC=C3C2=C2OCOC2=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C16H9NO6/c18-16(19)10-6-12-15(23-7-22-12)14-9-4-2-1-3-8(9)5-11(13(10)14)17(20)21/h1-6H,7H2,(H,18,19)

InChI Key

MEEXETVZNQYRSP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aristolochic acids and derivatives. These are organic heterocyclic compounds with a structure characterized by a nitrophenanthro[3,4-d][1,3]dioxole ring system substituted at position 5, 6, and 8 by a carboxyl group (or a derivative thereof), a nitro group, and a methoxy group, respectively.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Aristolochic acids and derivatives

Direct Parent

Aristolochic acids and derivatives

Alternative Parents

Substituents

Aristolochic acid or derivatives
1-naphthalenecarboxylic acid
1-naphthalenecarboxylic acid or derivatives
1-nitronaphthalene
2-nitronaphthalene
Naphthalene
Benzodioxole
Nitroaromatic compound
C-nitro compound
Organic nitro compound
Acetal
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Organic oxoazanium
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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	2.68	ALOGPS
logP	3.17	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.15	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	98.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.3 m³·mol⁻¹	ChemAxon
Polarizability	29.27 Å³	ChemAxon
Number of Rings	4	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]+	162.533	30932474
DeepCCS	[M-H]-	160.175	30932474
DeepCCS	[M-2H]-	193.213	30932474
DeepCCS	[M+Na]+	168.927	30932474
AllCCS	[M+H]+	167.3	32859911
AllCCS	[M+H-H2O]+	163.8	32859911
AllCCS	[M+NH4]+	170.6	32859911
AllCCS	[M+Na]+	171.5	32859911
AllCCS	[M-H]-	167.3	32859911
AllCCS	[M+Na-2H]-	165.9	32859911
AllCCS	[M+HCOO]-	164.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aristolochic acid B	OC(=O)C1=C2C(=CC3=CC=CC=C3C2=C2OCOC2=C1)[N+]([O-])=O	4269.4	Standard polar	33892256
Aristolochic acid B	OC(=O)C1=C2C(=CC3=CC=CC=C3C2=C2OCOC2=C1)[N+]([O-])=O	2668.6	Standard non polar	33892256
Aristolochic acid B	OC(=O)C1=C2C(=CC3=CC=CC=C3C2=C2OCOC2=C1)[N+]([O-])=O	3168.4	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 - Aristolochic acid B GC-MS (Non-derivatized) - 70eV, Positive	splash10-03xr-7098000000-ebfaf7169878dd222dba	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aristolochic acid B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aristolochic acid B GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aristolochic acid B GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aristolochic acid B 10V, Positive-QTOF	splash10-03di-0039000000-c0bade36c107e25b592c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aristolochic acid B 10V, Positive-QTOF	splash10-03yi-0595000000-4052e43d62308e0ded5a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aristolochic acid B 6V, Positive-QTOF	splash10-0a7i-0960000000-0b0f25793af6e6cfc6cf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aristolochic acid B 6V, Positive-QTOF	splash10-0zgi-0961000000-0b98498eaf56c51b659f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aristolochic acid B 30V, Positive-QTOF	splash10-0fk9-0890000000-296fb102d2029f3224a1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aristolochic acid B 50V, Positive-QTOF	splash10-004r-0900000000-2ebcf087f87218761749	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aristolochic acid B 6V, Positive-QTOF	splash10-004r-0900000000-20cdbeecc30301641112	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aristolochic acid B 30V, Positive-QTOF	splash10-00l6-0930000000-58d2550f800097426a02	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aristolochic acid B 50V, Positive-QTOF	splash10-0gw0-0900000000-6167ebcc76049e2e22a6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aristolochic acid B 10V, Positive-QTOF	splash10-03di-0069000000-3b07f17a2df4f5fd425b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aristolochic acid B 10V, Positive-QTOF	splash10-0gb9-0291000000-b53f05eba45bd9439b66	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aristolochic acid B 10V, Positive-QTOF	splash10-0zgi-0961000000-7a72484f2649c21b74f4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aristolochic acid B 10V, Positive-QTOF	splash10-03di-0079000000-d3c1f5e1ca56aedea4d4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aristolochic acid B 50V, Positive-QTOF	splash10-0udi-0900000000-46f177df77f6a744f491	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aristolochic acid B 30V, Positive-QTOF	splash10-0a7i-0960000000-fb364f1eae3dac8adac9	2021-09-20	HMDB team, MONA	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

C00021671

Chemspider ID

97250

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Aristolochic acid

METLIN ID

Not Available

PubChem Compound

108168

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 Aristolochic acid B (HMDB0248599)

MOL for HMDB0248599 (Aristolochic acid B)

3D MOL for HMDB0248599 (Aristolochic acid B)

3D SDF for HMDB0248599 (Aristolochic acid B)

3D-SDF for HMDB0248599 (Aristolochic acid B)

PDB for HMDB0248599 (Aristolochic acid B)

3D PDB for HMDB0248599 (Aristolochic acid B)

SMILES for HMDB0248599 (Aristolochic acid B)

INCHI for HMDB0248599 (Aristolochic acid B)

Structure for HMDB0248599 (Aristolochic acid B)

3D Structure for HMDB0248599 (Aristolochic acid B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra