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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:54:32 UTC

Update Date

2021-09-26 23:06:42 UTC

HMDB ID

HMDB0253461

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Indirubin-3'-monoxime

Description

INDIRUBIN-3'-MONOXIME, also known as indirubin 3'-oxime, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. Based on a literature review very few articles have been published on INDIRUBIN-3'-MONOXIME. This compound has been identified in human blood as reported by (PMID: 31557052 ). Indirubin-3'-monoxime is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Indirubin-3'-monoxime 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

HMDB0253461
     RDKit          3D
Indirubin-3'-monoxime
 32 35  0  0  0  0  0  0  0  0999 V2000
    0.3023    1.3527   -3.0640 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457    0.3951   -2.2983 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050    0.2744   -1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4438   -0.1075    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8914   -0.5504    0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1075   -1.4112    1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681   -1.9648    2.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3934   -1.6067    1.9008 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0510   -0.8874    0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4021   -0.7089    0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8876    0.1080   -0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951    0.7680   -1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6302    0.5828   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367   -0.2246    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427   -0.0970    0.9761 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6518    0.2682    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9807    0.4294    0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9460    0.8267   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    1.0709   -1.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2512    0.9130   -1.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2797    0.5101   -0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6142   -2.5866    1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8268   -2.1973    2.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0898   -1.2377    1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9528    0.2084   -0.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3045    1.4161   -1.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9497    1.1232   -1.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828   -0.3465    1.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2660    0.2375    1.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9926    0.9550    0.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2786    1.3861   -2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9314    1.1012   -2.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  4 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  3  1  0
 14  5  1  0
 21 16  1  0
 14  9  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
M  END


  Mrv1652309112113542D          

 21 24  0  0  0  0            999 V2000
   -1.0977   -2.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8823   -2.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0538   -1.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4407   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4846   -2.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6561   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4407   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4012    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    1.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
  7 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  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253461

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C(C2=C(N=O)C3=CC=CC=C3N2)C2=CC=CC=C2N1

> <INCHI_IDENTIFIER>
InChI=1S/C16H11N3O2/c20-16-13(9-5-1-3-7-11(9)18-16)15-14(19-21)10-6-2-4-8-12(10)17-15/h1-8,17-18,20H

> <INCHI_KEY>
FQCPPVRJPILDIK-UHFFFAOYSA-N

> <FORMULA>
C16H11N3O2

> <MOLECULAR_WEIGHT>
277.283

> <EXACT_MASS>
277.085126606

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.78218165665794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-nitroso-1H,1'H-[2,3'-biindole]-2'-ol

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
3.601430038333333

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.835344547566502

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.319182068557714

> <JCHEM_PKA_STRONGEST_BASIC>
-0.12023541001920812

> <JCHEM_POLAR_SURFACE_AREA>
81.23999999999998

> <JCHEM_REFRACTIVITY>
80.05230000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-nitroso-1H,1'H-[2,3'-biindole]-2'-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253461
     RDKit          3D
Indirubin-3'-monoxime
 32 35  0  0  0  0  0  0  0  0999 V2000
    0.3023    1.3527   -3.0640 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457    0.3951   -2.2983 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050    0.2744   -1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4438   -0.1075    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8914   -0.5504    0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1075   -1.4112    1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681   -1.9648    2.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3934   -1.6067    1.9008 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0510   -0.8874    0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4021   -0.7089    0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8876    0.1080   -0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951    0.7680   -1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6302    0.5828   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367   -0.2246    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427   -0.0970    0.9761 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6518    0.2682    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9807    0.4294    0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9460    0.8267   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    1.0709   -1.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2512    0.9130   -1.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2797    0.5101   -0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6142   -2.5866    1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8268   -2.1973    2.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0898   -1.2377    1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9528    0.2084   -0.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3045    1.4161   -1.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9497    1.1232   -1.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828   -0.3465    1.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2660    0.2375    1.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9926    0.9550    0.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2786    1.3861   -2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9314    1.1012   -2.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  4 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  3  1  0
 14  5  1  0
 21 16  1  0
 14  9  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -2.049  -5.086   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.514  -4.610   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.834  -3.103   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.689  -2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.225  -2.549   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.905  -4.055   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.225  -0.057   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -2.689  -0.533   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      -0.749   1.408   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.126  -2.549   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       1.650   1.408   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       2.680   2.552   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8                                                            
CONECT   11    7   12   19                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   11                                                       
CONECT   20   12   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0253461
HETATM    1  O1  UNL     1       0.302   1.353  -3.064  1.00  0.00           O  
HETATM    2  N1  UNL     1       0.246   0.395  -2.298  1.00  0.00           N  
HETATM    3  C1  UNL     1       0.905   0.274  -1.063  1.00  0.00           C  
HETATM    4  C2  UNL     1       0.444  -0.107   0.163  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.891  -0.550   0.597  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.108  -1.411   1.684  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.068  -1.965   2.410  1.00  0.00           O  
HETATM    8  N2  UNL     1      -2.393  -1.607   1.901  1.00  0.00           N  
HETATM    9  C5  UNL     1      -3.051  -0.887   0.975  1.00  0.00           C  
HETATM   10  C6  UNL     1      -4.402  -0.709   0.745  1.00  0.00           C  
HETATM   11  C7  UNL     1      -4.888   0.108  -0.266  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.995   0.768  -1.073  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.630   0.583  -0.837  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.137  -0.225   0.158  1.00  0.00           C  
HETATM   15  N3  UNL     1       1.543  -0.097   0.976  1.00  0.00           N  
HETATM   16  C11 UNL     1       2.652   0.268   0.332  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.981   0.429   0.707  1.00  0.00           C  
HETATM   18  C13 UNL     1       4.946   0.827  -0.179  1.00  0.00           C  
HETATM   19  C14 UNL     1       4.572   1.071  -1.482  1.00  0.00           C  
HETATM   20  C15 UNL     1       3.251   0.913  -1.864  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.280   0.510  -0.960  1.00  0.00           C  
HETATM   22  H1  UNL     1       0.614  -2.587   1.956  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.827  -2.197   2.638  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.090  -1.238   1.394  1.00  0.00           H  
HETATM   25  H4  UNL     1      -5.953   0.208  -0.398  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.305   1.416  -1.873  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.950   1.123  -1.445  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.483  -0.347   1.981  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.266   0.238   1.723  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.993   0.955   0.111  1.00  0.00           H  
HETATM   31  H10 UNL     1       5.279   1.386  -2.231  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.931   1.101  -2.893  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   15
CONECT    5    6    6   14
CONECT    6    7    8
CONECT    7   22
CONECT    8    9   23
CONECT    9   10   10   14
CONECT   10   11   24
CONECT   11   12   12   25
CONECT   12   13   26
CONECT   13   14   14   27
CONECT   15   16   28
CONECT   16   17   17   21
CONECT   17   18   29
CONECT   18   19   19   30
CONECT   19   20   31
CONECT   20   21   21   32
END

HMDB0253461
     RDKit          3D
Indirubin-3'-monoxime
 32 35  0  0  0  0  0  0  0  0999 V2000
    0.3023    1.3527   -3.0640 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457    0.3951   -2.2983 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050    0.2744   -1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4438   -0.1075    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8914   -0.5504    0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1075   -1.4112    1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681   -1.9648    2.4098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3934   -1.6067    1.9008 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0510   -0.8874    0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4021   -0.7089    0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8876    0.1080   -0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951    0.7680   -1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6302    0.5828   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367   -0.2246    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427   -0.0970    0.9761 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6518    0.2682    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9807    0.4294    0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9460    0.8267   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    1.0709   -1.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2512    0.9130   -1.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2797    0.5101   -0.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6142   -2.5866    1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8268   -2.1973    2.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0898   -1.2377    1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9528    0.2084   -0.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3045    1.4161   -1.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9497    1.1232   -1.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828   -0.3465    1.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2660    0.2375    1.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9926    0.9550    0.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2786    1.3861   -2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9314    1.1012   -2.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  4 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  3  1  0
 14  5  1  0
 21 16  1  0
 14  9  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Indirubin 3'-oxime	MeSH

Chemical Formula

C₁₆H₁₁N₃O₂

Average Molecular Weight

277.283

Monoisotopic Molecular Weight

277.085126606

IUPAC Name

3-nitroso-1H,1'H-[2,3'-biindole]-2'-ol

Traditional Name

3-nitroso-1H,1'H-[2,3'-biindole]-2'-ol

CAS Registry Number

Not Available

SMILES

OC1=C(C2=C(N=O)C3=CC=CC=C3N2)C2=CC=CC=C2N1

InChI Identifier

InChI=1S/C16H11N3O2/c20-16-13(9-5-1-3-7-11(9)18-16)15-14(19-21)10-6-2-4-8-12(10)17-15/h1-8,17-18,20H

InChI Key

FQCPPVRJPILDIK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Hydroxyindoles

Direct Parent

Hydroxyindoles

Alternative Parents

Substituents

Hydroxyindole
Indole
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Azacycle
C-nitroso compound
Organic nitroso compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organic anion
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)

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	3.64	ALOGPS
logP	3.6	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.32	ChemAxon
pKa (Strongest Basic)	-0.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	81.24 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.05 m³·mol⁻¹	ChemAxon
Polarizability	28.78 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]+	164.354	30932474
DeepCCS	[M-H]-	161.996	30932474
DeepCCS	[M-2H]-	194.883	30932474
DeepCCS	[M+Na]+	170.447	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Indirubin-3'-monoxime	OC1=C(C2=C(N=O)C3=CC=CC=C3N2)C2=CC=CC=C2N1	3614.8	Standard polar	33892256
Indirubin-3'-monoxime	OC1=C(C2=C(N=O)C3=CC=CC=C3N2)C2=CC=CC=C2N1	2992.8	Standard non polar	33892256
Indirubin-3'-monoxime	OC1=C(C2=C(N=O)C3=CC=CC=C3N2)C2=CC=CC=C2N1	3205.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Indirubin-3'-monoxime,2TMS,isomer #1	C[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3[NH]2)C2=CC=CC=C2N1[Si](C)(C)C	2777.0	Semi standard non polar	33892256
Indirubin-3'-monoxime,2TMS,isomer #1	C[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3[NH]2)C2=CC=CC=C2N1[Si](C)(C)C	2763.0	Standard non polar	33892256
Indirubin-3'-monoxime,2TMS,isomer #1	C[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3[NH]2)C2=CC=CC=C2N1[Si](C)(C)C	3380.7	Standard polar	33892256
Indirubin-3'-monoxime,2TMS,isomer #2	C[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C)C2=CC=CC=C2[NH]1	2826.9	Semi standard non polar	33892256
Indirubin-3'-monoxime,2TMS,isomer #2	C[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C)C2=CC=CC=C2[NH]1	2723.6	Standard non polar	33892256
Indirubin-3'-monoxime,2TMS,isomer #2	C[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C)C2=CC=CC=C2[NH]1	3344.3	Standard polar	33892256
Indirubin-3'-monoxime,2TMS,isomer #3	C[Si](C)(C)N1C(O)=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C)C2=CC=CC=C21	2912.9	Semi standard non polar	33892256
Indirubin-3'-monoxime,2TMS,isomer #3	C[Si](C)(C)N1C(O)=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C)C2=CC=CC=C21	2765.2	Standard non polar	33892256
Indirubin-3'-monoxime,2TMS,isomer #3	C[Si](C)(C)N1C(O)=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C)C2=CC=CC=C21	3340.8	Standard polar	33892256
Indirubin-3'-monoxime,3TMS,isomer #1	C[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C)C2=CC=CC=C2N1[Si](C)(C)C	2895.8	Semi standard non polar	33892256
Indirubin-3'-monoxime,3TMS,isomer #1	C[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C)C2=CC=CC=C2N1[Si](C)(C)C	2784.7	Standard non polar	33892256
Indirubin-3'-monoxime,3TMS,isomer #1	C[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C)C2=CC=CC=C2N1[Si](C)(C)C	3095.1	Standard polar	33892256
Indirubin-3'-monoxime,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3[NH]2)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C	3142.8	Semi standard non polar	33892256
Indirubin-3'-monoxime,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3[NH]2)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C	3157.2	Standard non polar	33892256
Indirubin-3'-monoxime,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3[NH]2)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C	3538.5	Standard polar	33892256
Indirubin-3'-monoxime,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C(C)(C)C)C2=CC=CC=C2[NH]1	3165.3	Semi standard non polar	33892256
Indirubin-3'-monoxime,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C(C)(C)C)C2=CC=CC=C2[NH]1	3107.8	Standard non polar	33892256
Indirubin-3'-monoxime,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C(C)(C)C)C2=CC=CC=C2[NH]1	3490.4	Standard polar	33892256
Indirubin-3'-monoxime,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(O)=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	3174.7	Semi standard non polar	33892256
Indirubin-3'-monoxime,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(O)=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	3137.1	Standard non polar	33892256
Indirubin-3'-monoxime,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(O)=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C(C)(C)C)C2=CC=CC=C21	3459.9	Standard polar	33892256
Indirubin-3'-monoxime,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C(C)(C)C)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C	3314.8	Semi standard non polar	33892256
Indirubin-3'-monoxime,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C(C)(C)C)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C	3346.0	Standard non polar	33892256
Indirubin-3'-monoxime,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C2=C(N=O)C3=CC=CC=C3N2[Si](C)(C)C(C)(C)C)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C	3366.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Indirubin-3'-monoxime GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-0190000000-8b788807bc41eb27d93e	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indirubin-3'-monoxime GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indirubin-3'-monoxime GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indirubin-3'-monoxime GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indirubin-3'-monoxime GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indirubin-3'-monoxime GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indirubin-3'-monoxime GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indirubin-3'-monoxime GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	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 - Indirubin-3'-monoxime 10V, Positive-QTOF	splash10-004i-0090000000-c740ea935b307aaf5d3b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indirubin-3'-monoxime 20V, Positive-QTOF	splash10-03fr-0090000000-92687fdf0965b575b380	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indirubin-3'-monoxime 40V, Positive-QTOF	splash10-03e9-0090000000-2213646e74ca6d39e049	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indirubin-3'-monoxime 10V, Negative-QTOF	splash10-004i-0090000000-f30e90eade37550d9819	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indirubin-3'-monoxime 20V, Negative-QTOF	splash10-004i-0090000000-d5cf84591cb04dab2a5c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indirubin-3'-monoxime 40V, Negative-QTOF	splash10-0a4i-0930000000-7d97ce030739e49581e5	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

23207173

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3707

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 Indirubin-3'-monoxime (HMDB0253461)

MOL for HMDB0253461 (Indirubin-3'-monoxime)

3D MOL for HMDB0253461 (Indirubin-3'-monoxime)

3D SDF for HMDB0253461 (Indirubin-3'-monoxime)

3D-SDF for HMDB0253461 (Indirubin-3'-monoxime)

PDB for HMDB0253461 (Indirubin-3'-monoxime)

3D PDB for HMDB0253461 (Indirubin-3'-monoxime)

SMILES for HMDB0253461 (Indirubin-3'-monoxime)

INCHI for HMDB0253461 (Indirubin-3'-monoxime)

Structure for HMDB0253461 (Indirubin-3'-monoxime)

3D Structure for HMDB0253461 (Indirubin-3'-monoxime)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra