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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 02:01:39 UTC

Update Date

2021-09-26 22:58:57 UTC

HMDB ID

HMDB0248598

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Aristolochic acid

Description

aristolochic acid 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. aristolochic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on aristolochic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Aristolochic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Aristolochic acid 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


  Mrv0541 08291401172D          

 25 28  0  0  0  0            999 V2000
    4.9832    1.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984    2.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659    1.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5933    1.9024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7856   -0.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0693    0.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2495    2.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1283    1.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232    0.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256   -0.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530   -0.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557    1.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317    0.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581   -0.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3957    0.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008    1.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880   -1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0154   -1.3290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2829   -1.7085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1446   -1.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6459   -2.0666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7104   -1.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2506    0.6337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190    1.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5662    2.0225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  2  0  0  0  0
  9  8  1  0  0  0  0
 10  6  2  0  0  0  0
 11  5  1  0  0  0  0
 12  4  2  0  0  0  0
 12  9  1  0  0  0  0
 13  6  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  2  0  0  0  0
 15  8  2  0  0  0  0
 15 14  1  0  0  0  0
 16 13  2  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 17  2  0  0  0  0
 20 17  1  0  0  0  0
 21 18  2  0  0  0  0
 22 18  2  0  0  0  0
 23  1  1  0  0  0  0
 23 12  1  0  0  0  0
 24  7  1  0  0  0  0
 24 13  1  0  0  0  0
 25  7  1  0  0  0  0
 25 16  1  0  0  0  0
M  END

HMDB0248598
     RDKit          3D
Aristolochic acid
 36 39  0  0  0  0  0  0  0  0999 V2000
    4.8874   -1.6153    0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4904   -1.6734    0.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7836   -0.4709    0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    0.7325    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7341    1.9116    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3534    1.9343    0.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7061    0.7370   -0.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4072   -0.4678    0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7922   -1.6647   -0.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5978   -1.7193   -0.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0579   -3.0061   -0.6456 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.5553   -3.9950    0.0144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9955   -3.3235   -1.5545 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2981   -0.5577   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6488   -0.5925   -0.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5178   -1.7437   -0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4870   -1.8751   -1.2362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3551   -2.6535    0.5801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3609    0.6099   -0.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7005    1.7943   -0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3386    1.8699   -0.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6349    0.6799   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0729    3.2272   -0.1914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2485    3.8380    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2234    3.1120   -0.4883 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3690   -1.0541   -0.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3601   -2.5910    0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1128   -1.0472    1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5085    0.6920    0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2594    2.8563    0.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9015    2.8981    0.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3349   -2.6116   -0.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1380   -3.2228    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4226    0.5616   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4714    3.5156    1.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3077    4.9149    0.1506 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
  8  3  1  0
 22 14  1  0
 22  7  1  0
 25 20  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  9 32  1  0
 18 33  1  0
 19 34  1  0
 24 35  1  0
 24 36  1  0
M  CHG  2  11   1  13  -1
M  END


  Mrv0541 08291401172D          

 25 28  0  0  0  0            999 V2000
    4.9832    1.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984    2.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659    1.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5933    1.9024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7856   -0.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0693    0.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2495    2.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1283    1.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232    0.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256   -0.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530   -0.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557    1.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317    0.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581   -0.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3957    0.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008    1.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880   -1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0154   -1.3290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2829   -1.7085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1446   -1.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6459   -2.0666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7104   -1.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2506    0.6337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190    1.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5662    2.0225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  2  0  0  0  0
  9  8  1  0  0  0  0
 10  6  2  0  0  0  0
 11  5  1  0  0  0  0
 12  4  2  0  0  0  0
 12  9  1  0  0  0  0
 13  6  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  2  0  0  0  0
 15  8  2  0  0  0  0
 15 14  1  0  0  0  0
 16 13  2  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 17  2  0  0  0  0
 20 17  1  0  0  0  0
 21 18  2  0  0  0  0
 22 18  2  0  0  0  0
 23  1  1  0  0  0  0
 23 12  1  0  0  0  0
 24  7  1  0  0  0  0
 24 13  1  0  0  0  0
 25  7  1  0  0  0  0
 25 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248598

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=CC2=C3C4=C(OCO4)C=C(C(O)=O)C3=C(C=C12)N(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H11NO7/c1-23-12-4-2-3-8-9(12)5-11(18(21)22)14-10(17(19)20)6-13-16(15(8)14)25-7-24-13/h2-6H,7H2,1H3,(H,19,20)

> <INCHI_KEY>
BBFQZRXNYIEMAW-UHFFFAOYSA-N

> <FORMULA>
C17H11NO7

> <MOLECULAR_WEIGHT>
341.2717

> <EXACT_MASS>
341.053551711

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
32.27237509052989

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-methoxy-9-nitro-14,16-dioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1,3,5,7,9,11,13(17)-heptaene-11-carboxylic acid

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
3.0153286286666665

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.324096413497671

> <JCHEM_PKA_STRONGEST_BASIC>
-4.508673132643244

> <JCHEM_POLAR_SURFACE_AREA>
110.81000000000002

> <JCHEM_REFRACTIVITY>
85.76939999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
birthwort

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248598
     RDKit          3D
Aristolochic acid
 36 39  0  0  0  0  0  0  0  0999 V2000
    4.8874   -1.6153    0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4904   -1.6734    0.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7836   -0.4709    0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    0.7325    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7341    1.9116    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3534    1.9343    0.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7061    0.7370   -0.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4072   -0.4678    0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7922   -1.6647   -0.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5978   -1.7193   -0.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0579   -3.0061   -0.6456 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.5553   -3.9950    0.0144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9955   -3.3235   -1.5545 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2981   -0.5577   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6488   -0.5925   -0.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5178   -1.7437   -0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4870   -1.8751   -1.2362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3551   -2.6535    0.5801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3609    0.6099   -0.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7005    1.7943   -0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3386    1.8699   -0.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6349    0.6799   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0729    3.2272   -0.1914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2485    3.8380    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2234    3.1120   -0.4883 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3690   -1.0541   -0.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3601   -2.5910    0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1128   -1.0472    1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5085    0.6920    0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2594    2.8563    0.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9015    2.8981    0.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3349   -2.6116   -0.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1380   -3.2228    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4226    0.5616   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4714    3.5156    1.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3077    4.9149    0.1506 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
  8  3  1  0
 22 14  1  0
 22  7  1  0
 25 20  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  9 32  1  0
 18 33  1  0
 19 34  1  0
 24 35  1  0
 24 36  1  0
M  CHG  2  11   1  13  -1
M  END

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0       9.302   1.891   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.410   4.381   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.043   3.673   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.708   3.551   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.200  -0.234   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.129   0.009   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.466   4.006   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.973   2.134   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.270   1.304   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.168  -0.821   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.832  -0.942   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.637   2.013   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.059   1.548   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.535  -0.112   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.605   1.426   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.308   2.256   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.098  -2.359   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.762  -2.481   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       2.395  -3.189   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.270  -3.068   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.072  -3.858   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.059  -3.311   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.935   1.183   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.156   2.629   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.057   3.775   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2    3    4                                                       
CONECT    3    2    8                                                       
CONECT    4    2   12                                                       
CONECT    5    9   11                                                       
CONECT    6   10   13                                                       
CONECT    7   24   25                                                       
CONECT    8    3    9   15                                                  
CONECT    9    5    8   12                                                  
CONECT   10    6   14   17                                                  
CONECT   11    5   14   18                                                  
CONECT   12    4    9   23                                                  
CONECT   13    6   16   24                                                  
CONECT   14   10   11   15                                                  
CONECT   15    8   14   16                                                  
CONECT   16   13   15   25                                                  
CONECT   17   10   19   20                                                  
CONECT   18   11   21   22                                                  
CONECT   19   17                                                            
CONECT   20   17                                                            
CONECT   21   18                                                            
CONECT   22   18                                                            
CONECT   23    1   12                                                       
CONECT   24    7   13                                                       
CONECT   25    7   16                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0248598
HETATM    1  C1  UNL     1       4.887  -1.615   0.572  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.490  -1.673   0.340  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.784  -0.471   0.269  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.432   0.732   0.421  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.734   1.912   0.350  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.353   1.934   0.123  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.706   0.737  -0.029  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.407  -0.468   0.041  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.792  -1.665  -0.116  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.598  -1.719  -0.356  1.00  0.00           C  
HETATM   11  N1  UNL     1      -1.058  -3.006  -0.646  1.00  0.00           N1+
HETATM   12  O2  UNL     1      -0.555  -3.995   0.014  1.00  0.00           O  
HETATM   13  O3  UNL     1      -1.995  -3.323  -1.554  1.00  0.00           O1-
HETATM   14  C10 UNL     1      -1.298  -0.558  -0.411  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.649  -0.592  -0.578  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.518  -1.744  -0.411  1.00  0.00           C  
HETATM   17  O4  UNL     1      -4.487  -1.875  -1.236  1.00  0.00           O  
HETATM   18  O5  UNL     1      -3.355  -2.654   0.580  1.00  0.00           O  
HETATM   19  C13 UNL     1      -3.361   0.610  -0.620  1.00  0.00           C  
HETATM   20  C14 UNL     1      -2.701   1.794  -0.479  1.00  0.00           C  
HETATM   21  C15 UNL     1      -1.339   1.870  -0.291  1.00  0.00           C  
HETATM   22  C16 UNL     1      -0.635   0.680  -0.251  1.00  0.00           C  
HETATM   23  O6  UNL     1      -1.073   3.227  -0.191  1.00  0.00           O  
HETATM   24  C17 UNL     1      -2.249   3.838   0.290  1.00  0.00           C  
HETATM   25  O7  UNL     1      -3.223   3.112  -0.488  1.00  0.00           O  
HETATM   26  H1  UNL     1       5.369  -1.054  -0.254  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.360  -2.591   0.645  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.113  -1.047   1.523  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.508   0.692   0.596  1.00  0.00           H  
HETATM   30  H5  UNL     1       3.259   2.856   0.471  1.00  0.00           H  
HETATM   31  H6  UNL     1       0.901   2.898   0.085  1.00  0.00           H  
HETATM   32  H7  UNL     1       1.335  -2.612  -0.064  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.138  -3.223   0.925  1.00  0.00           H  
HETATM   34  H9  UNL     1      -4.423   0.562  -0.765  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.471   3.516   1.345  1.00  0.00           H  
HETATM   36  H11 UNL     1      -2.308   4.915   0.151  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   29
CONECT    5    6    6   30
CONECT    6    7   31
CONECT    7    8    8   22
CONECT    8    9
CONECT    9   10   10   32
CONECT   10   11   14
CONECT   11   12   12   13
CONECT   14   15   15   22
CONECT   15   16   19
CONECT   16   17   17   18
CONECT   18   33
CONECT   19   20   20   34
CONECT   20   21   25
CONECT   21   22   22   23
CONECT   23   24
CONECT   24   25   35   36
END

HMDB0248598
     RDKit          3D
Aristolochic acid
 36 39  0  0  0  0  0  0  0  0999 V2000
    4.8874   -1.6153    0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4904   -1.6734    0.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7836   -0.4709    0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    0.7325    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7341    1.9116    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3534    1.9343    0.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7061    0.7370   -0.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4072   -0.4678    0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7922   -1.6647   -0.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5978   -1.7193   -0.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0579   -3.0061   -0.6456 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.5553   -3.9950    0.0144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9955   -3.3235   -1.5545 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2981   -0.5577   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6488   -0.5925   -0.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5178   -1.7437   -0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4870   -1.8751   -1.2362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3551   -2.6535    0.5801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3609    0.6099   -0.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7005    1.7943   -0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3386    1.8699   -0.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6349    0.6799   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0729    3.2272   -0.1914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2485    3.8380    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2234    3.1120   -0.4883 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3690   -1.0541   -0.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3601   -2.5910    0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1128   -1.0472    1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5085    0.6920    0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2594    2.8563    0.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9015    2.8981    0.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3349   -2.6116   -0.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1380   -3.2228    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4226    0.5616   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4714    3.5156    1.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3077    4.9149    0.1506 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
  8  3  1  0
 22 14  1  0
 22  7  1  0
 25 20  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  9 32  1  0
 18 33  1  0
 19 34  1  0
 24 35  1  0
 24 36  1  0
M  CHG  2  11   1  13  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4-Methylenedioxy-8-methoxy-10-nitro-1-phenanthrenecarboxylic acid	ChEBI
8-Methoxy-6-nitrophenanthol (3,4-D) 1,3-dioxole-5-carboxylic acid	ChEBI
Aristolochic acid a	ChEBI
Aristolochic acid I	ChEBI
Aristolochic acid-I	ChEBI
Aristolochin	ChEBI
3,4-Methylenedioxy-8-methoxy-10-nitro-1-phenanthrenecarboxylate	Generator
8-Methoxy-6-nitrophenanthol (3,4-D) 1,3-dioxole-5-carboxylate	Generator
Aristolochate a	Generator
Aristolochate I	Generator
Aristolochate-I	Generator
Aristolochate	Generator
Aristolochic acid I, sodium salt	MeSH
8-Methoxy-6-nitrophenanthro(3,4-D)-1,3-dioxole-5-carboxylic acid	MeSH
Tardolyt	MeSH
Sodium aristolochate	MeSH

Chemical Formula

C₁₇H₁₁NO₇

Average Molecular Weight

341.2717

Monoisotopic Molecular Weight

341.053551711

IUPAC Name

6-methoxy-9-nitro-14,16-dioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]heptadeca-1,3,5,7,9,11,13(17)-heptaene-11-carboxylic acid

Traditional Name

birthwort

CAS Registry Number

Not Available

SMILES

COC1=CC=CC2=C3C4=C(OCO4)C=C(C(O)=O)C3=C(C=C12)N(=O)=O

InChI Identifier

InChI=1S/C17H11NO7/c1-23-12-4-2-3-8-9(12)5-11(18(21)22)14-10(17(19)20)6-13-16(15(8)14)25-7-24-13/h2-6H,7H2,1H3,(H,19,20)

InChI Key

BBFQZRXNYIEMAW-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
Anisole
Alkyl aryl ether
Organic nitro compound
C-nitro compound
Acetal
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

C-nitro compound (CHEBI:2825 )
monocarboxylic acid (CHEBI:2825 )
cyclic acetal (CHEBI:2825 )
phenanthrenes (CHEBI:2825 )
Isoquinoline alkaloids (C08469 )

Ontology

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	2.69	ALOGPS
logP	3.02	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	110.81 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.77 m³·mol⁻¹	ChemAxon
Polarizability	32.27 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-2H]-	212.32	30932474
DeepCCS	[M+Na]+	188.462	30932474
AllCCS	[M+H]+	175.0	32859911
AllCCS	[M+H-H2O]+	171.7	32859911
AllCCS	[M+NH4]+	178.0	32859911
AllCCS	[M+Na]+	178.9	32859911
AllCCS	[M-H]-	175.7	32859911
AllCCS	[M+Na-2H]-	174.5	32859911
AllCCS	[M+HCOO]-	173.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aristolochic acid	COC1=CC=CC2=C3C4=C(OCO4)C=C(C(O)=O)C3=C(C=C12)N(=O)=O	4534.0	Standard polar	33892256
Aristolochic acid	COC1=CC=CC2=C3C4=C(OCO4)C=C(C(O)=O)C3=C(C=C12)N(=O)=O	2934.7	Standard non polar	33892256
Aristolochic acid	COC1=CC=CC2=C3C4=C(OCO4)C=C(C(O)=O)C3=C(C=C12)N(=O)=O	3397.3	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 GC-MS (Non-derivatized) - 70eV, Positive	splash10-01oy-3097000000-da70a568598192c4149d	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aristolochic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aristolochic acid 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 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolochic acid 10V, Positive-QTOF	splash10-0006-0009000000-192503bd944b4098f295	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolochic acid 20V, Positive-QTOF	splash10-0006-0019000000-36268a06fdb878508480	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolochic acid 40V, Positive-QTOF	splash10-022d-0059000000-e1c393e1f4dcf97ab02c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolochic acid 10V, Negative-QTOF	splash10-0006-0009000000-ec56c61ed56ce4fdd6d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolochic acid 20V, Negative-QTOF	splash10-0006-0009000000-0f6cf8b2fee975ef3311	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolochic acid 40V, Negative-QTOF	splash10-0016-2093000000-237334dcb4e6c37619ae	2016-08-03	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

C00001526

Chemspider ID

2149

KEGG Compound ID

C08469

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Aristolochic_acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

2825

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 (HMDB0248598)

MOL for HMDB0248598 (Aristolochic acid)

3D MOL for HMDB0248598 (Aristolochic acid)

3D SDF for HMDB0248598 (Aristolochic acid)

3D-SDF for HMDB0248598 (Aristolochic acid)

PDB for HMDB0248598 (Aristolochic acid)

3D PDB for HMDB0248598 (Aristolochic acid)

SMILES for HMDB0248598 (Aristolochic acid)

INCHI for HMDB0248598 (Aristolochic acid)

Structure for HMDB0248598 (Aristolochic acid)

3D Structure for HMDB0248598 (Aristolochic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra