NP-MRD: Showing NP-Card for aristolochic acid iv (NP0201320)

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Record Information

Version

2.0

Created at

2022-09-04 20:20:38 UTC

Updated at

2022-09-04 20:20:38 UTC

NP-MRD ID

NP0201320

Secondary Accession Numbers

None

Natural Product Identification

Common Name

aristolochic acid iv

Description

Aristolochic acid IV, also known as aristolochate IV, 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 iv is found in Aristolochia argentina, Aristolochia cucurbitifolia, Aristolochia manshuriensis, Aristolochia rigida and Aristolochia zollingeriana. Aristolochic acid IV is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191523152D          

 27 30  0  0  0  0            999 V2000
    2.0501   -2.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7827   -2.4733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203   -1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1254   -1.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1630   -0.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4680    0.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355   -0.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8955   -0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9331    0.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6656    1.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3606    0.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0931    1.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7880    0.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7504   -0.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3377   -0.7105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9681   -1.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1524   -1.3246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179   -0.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3229   -0.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5904   -0.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1307    1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358    2.4064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8632    2.3413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7032    2.0269    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.0728    2.7645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0083    2.4716    0.0000 O   0  5  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  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 21  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 10 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  CHG  2  25   1  27  -1
M  END

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
   -4.6381    2.6819    0.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3715    2.2977    0.0926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6804    1.1676    0.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1747   -0.1430    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3045   -1.1963    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6252   -2.4384    0.1407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9550   -3.6909    0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9110   -0.9336   -0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0885   -2.0098   -0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3087   -1.7540   -0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0622   -2.9376    0.0526 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.9716   -2.9637    0.8992 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6725   -4.1295   -0.5118 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.7964   -0.5084   -0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1395   -0.2567   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1350   -1.2861   -0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8623   -2.1033   -1.6068 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2919   -1.3935    0.0362 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6009    1.0451   -0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7226    2.0692   -0.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3622    1.8904   -0.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9312    0.6084   -0.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323    0.3514   -0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2994    1.3904   -0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158    3.1512   -0.5153 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8012    4.0989   -0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9913    3.4413   -0.6407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3938    2.4766   -0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9849    2.2721    1.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6042    3.8284    0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2409   -0.2565    0.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4484   -4.1894    1.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6346   -4.3672   -0.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0155   -4.0363    0.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4388   -3.0188   -0.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5120   -2.1779    0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6770    1.2076   -0.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9478    2.3961   -0.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242    5.0517   -0.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9109    4.3653    0.7987 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  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
 10 14  1  0
 14 15  2  0
 15 19  1  0
 19 20  2  0
 20 27  1  0
 27 26  1  0
 26 25  1  0
 25 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 15 16  1  0
 16 18  1  0
 16 17  2  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
 24  3  1  0
 23  8  1  0
 22 14  1  0
 21 20  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  7 32  1  0
  7 33  1  0
  7 34  1  0
  9 35  1  0
 19 37  1  0
 26 39  1  0
 26 40  1  0
 24 38  1  0
 18 36  1  0
M  CHG  2  11   1  13  -1
M  END


  Mrv1533004191523152D          

 27 30  0  0  0  0            999 V2000
    2.0501   -2.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7827   -2.4733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8203   -1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1254   -1.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1630   -0.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4680    0.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355   -0.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8955   -0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9331    0.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6656    1.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3606    0.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0931    1.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7880    0.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7504   -0.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3377   -0.7105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9681   -1.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1524   -1.3246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179   -0.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3229   -0.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5904   -0.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1307    1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358    2.4064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8632    2.3413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7032    2.0269    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.0728    2.7645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0083    2.4716    0.0000 O   0  5  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  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 21  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 10 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  CHG  2  25   1  27  -1
M  END
> <DATABASE_ID>
NP0201320

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C=C(C3=C(C=C4OCOC4=C3C2=C1)C(O)=O)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H13NO8/c1-24-8-3-10-9(13(4-8)25-2)5-12(19(22)23)15-11(18(20)21)6-14-17(16(10)15)27-7-26-14/h3-6H,7H2,1-2H3,(H,20,21)

> <INCHI_KEY>
GYBINMVKWZEICQ-UHFFFAOYSA-N

> <FORMULA>
C18H13NO8

> <MOLECULAR_WEIGHT>
371.301

> <EXACT_MASS>
371.064116383

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
35.35156278394831

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,6-dimethoxy-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>
2.67

> <JCHEM_LOGP>
2.8576573630000004

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1526602643620594

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3468949109323205

> <JCHEM_POLAR_SURFACE_AREA>
117.36000000000001

> <JCHEM_REFRACTIVITY>
91.22839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,6-dimethoxy-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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       3.827  -5.325   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.194  -4.617   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.265  -3.078   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.967  -2.248   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.038  -0.710   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.740   0.120   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.373  -0.588   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.405  -0.002   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.475   1.537   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.843   2.245   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.140   1.415   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.507   2.124   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.804   1.294   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.734  -0.245   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.830  -1.326   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.141  -2.703   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.618  -2.473   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.367  -0.953   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.069  -0.123   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.702  -0.832   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.632  -2.370   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.577   3.662   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.280   4.492   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.945   4.370   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       6.913   3.784   0.000  0.00  0.00           N+1
HETATM   26  O   UNK     0       7.603   5.160   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.616   4.614   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   25                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   11   20                                                  
CONECT   20   19    8   21                                                  
CONECT   21   20    3                                                       
CONECT   22   12   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   10   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

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Synonyms

Value	Source
Aristolochate IV	Generator

Chemical Formula

C₁₈H₁₃NO₈

Average Mass

371.3010 Da

Monoisotopic Mass

371.06412 Da

IUPAC Name

4,6-dimethoxy-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

4,6-dimethoxy-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

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C2C=C(C3=C(C=C4OCOC4=C3C2=C1)C(O)=O)[N+]([O-])=O

InChI Identifier

InChI=1S/C18H13NO8/c1-24-8-3-10-9(13(4-8)25-2)5-12(19(22)23)15-11(18(20)21)6-14-17(16(10)15)27-7-26-14/h3-6H,7H2,1-2H3,(H,20,21)

InChI Key

GYBINMVKWZEICQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aristolochia argentina	LOTUS Database	35616633
Aristolochia cucurbitifolia	LOTUS Database	35616633
Aristolochia manshuriensis	LOTUS Database	35616633
Aristolochia rigida	LOTUS Database	35616633
Aristolochia zollingeriana	LOTUS Database	35616633

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

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	2.67	ALOGPS
logP	2.86	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.15	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	117.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.23 m³·mol⁻¹	ChemAxon
Polarizability	35.35 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

167493

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for aristolochic acid iv (NP0201320)

MOL for NP0201320 (aristolochic acid iv)

3D MOL for NP0201320 (aristolochic acid iv)

3D SDF for NP0201320 (aristolochic acid iv)

3D-SDF for NP0201320 (aristolochic acid iv)

PDB for NP0201320 (aristolochic acid iv)

3D PDB for NP0201320 (aristolochic acid iv)

SMILES for NP0201320 (aristolochic acid iv)

INCHI for NP0201320 (aristolochic acid iv)

Structure for NP0201320 (aristolochic acid iv)

3D Structure for NP0201320 (aristolochic acid iv)