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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:25:22 UTC

Update Date

2021-09-26 23:02:57 UTC

HMDB ID

HMDB0251118

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Diacerein

Description

Diacerein, also known as zondar, belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system. Diacerein is a drug which is used for the treatment of osteoarthritis affecting the hip or knee [l780]. Based on a literature review a significant number of articles have been published on Diacerein. This compound has been identified in human blood as reported by (PMID: 31557052 ). Diacerein is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Diacerein 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


  Mrv1533004251507472D          

 27 29  0  0  0  0            999 V2000
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 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  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 16 21  2  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  5 24  1  0  0  0  0
  9 24  2  0  0  0  0
 14 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  END

HMDB0251118
     RDKit          3D
Diacerein
 39 41  0  0  0  0  0  0  0  0999 V2000
   -3.6344    3.1465   -0.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3097    1.7152   -0.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1326    1.2882   -1.7760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831    0.7837    0.4260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8788   -0.5572    0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8619   -1.5061   -0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5881   -2.8343   -0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2703   -3.2251   -0.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2414   -2.3308   -0.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5737   -1.0023    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4569   -0.0880    0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7302    1.1388    0.5715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9369   -0.5161    0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9678    0.3807    0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561    1.7138    0.7556 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5245    2.6469   -0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1894    4.0402    0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6906    2.2923   -1.4508 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2607   -0.0972    0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5731   -1.4158    0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9483   -1.8933    0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1966   -3.1037   -0.0212 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0169   -1.0330    0.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5390   -2.3071    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2290   -1.8426    0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1466   -2.7760   -0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4381   -3.9908   -0.3403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8077    3.7038    0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9604    3.5881   -1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5353    3.2127    0.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8927   -1.1495    0.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4260   -3.4889   -0.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0396   -4.2595   -0.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4211    4.2229    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7549    4.7834   -0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801    4.1494   -0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0473    0.6292    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1457   -0.6630    1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7604   -3.3557   -0.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  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
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 14 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 10  5  1  0
 25 13  1  0
 26  9  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 19 37  1  0
 23 38  1  0
 24 39  1  0
M  END


  Mrv1533004251507472D          

 27 29  0  0  0  0            999 V2000
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 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  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 16 21  2  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  5 24  1  0  0  0  0
  9 24  2  0  0  0  0
 14 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251118

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1=CC=CC2=C1C(=O)C1=C(OC(C)=O)C=C(C=C1C2=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H12O8/c1-8(20)26-13-5-3-4-11-15(13)18(23)16-12(17(11)22)6-10(19(24)25)7-14(16)27-9(2)21/h3-7H,1-2H3,(H,24,25)

> <INCHI_KEY>
TYNLGDBUJLVSMA-UHFFFAOYSA-N

> <FORMULA>
C19H12O8

> <MOLECULAR_WEIGHT>
368.297

> <EXACT_MASS>
368.053217346

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
35.36938536794496

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5-bis(acetyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
1.7908109313333331

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3730348946098694

> <JCHEM_PKA_STRONGEST_BASIC>
-6.7556645440589325

> <JCHEM_POLAR_SURFACE_AREA>
124.04

> <JCHEM_REFRACTIVITY>
90.67199999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diacerein

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251118
     RDKit          3D
Diacerein
 39 41  0  0  0  0  0  0  0  0999 V2000
   -3.6344    3.1465   -0.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3097    1.7152   -0.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1326    1.2882   -1.7760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831    0.7837    0.4260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8788   -0.5572    0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8619   -1.5061   -0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5881   -2.8343   -0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2703   -3.2251   -0.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2414   -2.3308   -0.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5737   -1.0023    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4569   -0.0880    0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7302    1.1388    0.5715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9369   -0.5161    0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9678    0.3807    0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561    1.7138    0.7556 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5245    2.6469   -0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1894    4.0402    0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6906    2.2923   -1.4508 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2607   -0.0972    0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5731   -1.4158    0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9483   -1.8933    0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1966   -3.1037   -0.0212 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0169   -1.0330    0.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5390   -2.3071    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2290   -1.8426    0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1466   -2.7760   -0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4381   -3.9908   -0.3403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8077    3.7038    0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9604    3.5881   -1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5353    3.2127    0.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8927   -1.1495    0.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4260   -3.4889   -0.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0396   -4.2595   -0.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4211    4.2229    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7549    4.7834   -0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801    4.1494   -0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0473    0.6292    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1457   -0.6630    1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7604   -3.3557   -0.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  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
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 14 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 10  5  1  0
 25 13  1  0
 26  9  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 19 37  1  0
 23 38  1  0
 24 39  1  0
M  END

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   24                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   12   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    5    9                                                  
CONECT   25   14   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0251118
HETATM    1  C1  UNL     1      -3.634   3.147  -0.335  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.310   1.715  -0.587  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.133   1.288  -1.776  1.00  0.00           O  
HETATM    4  O2  UNL     1      -3.183   0.784   0.426  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.879  -0.557   0.188  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.862  -1.506  -0.020  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.588  -2.834  -0.257  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.270  -3.225  -0.287  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.241  -2.331  -0.088  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.574  -1.002   0.148  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.457  -0.088   0.353  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.730   1.139   0.572  1.00  0.00           O  
HETATM   13  C10 UNL     1       0.937  -0.516   0.319  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.968   0.381   0.519  1.00  0.00           C  
HETATM   15  O4  UNL     1       1.656   1.714   0.756  1.00  0.00           O  
HETATM   16  C12 UNL     1       1.525   2.647  -0.256  1.00  0.00           C  
HETATM   17  C13 UNL     1       1.189   4.040   0.120  1.00  0.00           C  
HETATM   18  O5  UNL     1       1.691   2.292  -1.451  1.00  0.00           O  
HETATM   19  C14 UNL     1       3.261  -0.097   0.472  1.00  0.00           C  
HETATM   20  C15 UNL     1       3.573  -1.416   0.238  1.00  0.00           C  
HETATM   21  C16 UNL     1       4.948  -1.893   0.195  1.00  0.00           C  
HETATM   22  O6  UNL     1       5.197  -3.104  -0.021  1.00  0.00           O  
HETATM   23  O7  UNL     1       6.017  -1.033   0.389  1.00  0.00           O  
HETATM   24  C17 UNL     1       2.539  -2.307   0.040  1.00  0.00           C  
HETATM   25  C18 UNL     1       1.229  -1.843   0.083  1.00  0.00           C  
HETATM   26  C19 UNL     1       0.147  -2.776  -0.125  1.00  0.00           C  
HETATM   27  O8  UNL     1       0.438  -3.991  -0.340  1.00  0.00           O  
HETATM   28  H1  UNL     1      -2.808   3.704   0.110  1.00  0.00           H  
HETATM   29  H2  UNL     1      -3.960   3.588  -1.301  1.00  0.00           H  
HETATM   30  H3  UNL     1      -4.535   3.213   0.340  1.00  0.00           H  
HETATM   31  H4  UNL     1      -4.893  -1.149   0.012  1.00  0.00           H  
HETATM   32  H5  UNL     1      -4.426  -3.489  -0.406  1.00  0.00           H  
HETATM   33  H6  UNL     1      -2.040  -4.260  -0.471  1.00  0.00           H  
HETATM   34  H7  UNL     1       1.421   4.223   1.177  1.00  0.00           H  
HETATM   35  H8  UNL     1       1.755   4.783  -0.487  1.00  0.00           H  
HETATM   36  H9  UNL     1       0.080   4.149  -0.052  1.00  0.00           H  
HETATM   37  H10 UNL     1       4.047   0.629   0.633  1.00  0.00           H  
HETATM   38  H11 UNL     1       6.146  -0.663   1.318  1.00  0.00           H  
HETATM   39  H12 UNL     1       2.760  -3.356  -0.147  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6    6   10
CONECT    6    7   31
CONECT    7    8    8   32
CONECT    8    9   33
CONECT    9   10   10   26
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   14   25
CONECT   14   15   19
CONECT   15   16
CONECT   16   17   18   18
CONECT   17   34   35   36
CONECT   19   20   20   37
CONECT   20   21   24
CONECT   21   22   22   23
CONECT   23   38
CONECT   24   25   25   39
CONECT   25   26
CONECT   26   27   27
END

HMDB0251118
     RDKit          3D
Diacerein
 39 41  0  0  0  0  0  0  0  0999 V2000
   -3.6344    3.1465   -0.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3097    1.7152   -0.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1326    1.2882   -1.7760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831    0.7837    0.4260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8788   -0.5572    0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8619   -1.5061   -0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5881   -2.8343   -0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2703   -3.2251   -0.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2414   -2.3308   -0.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5737   -1.0023    0.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4569   -0.0880    0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7302    1.1388    0.5715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9369   -0.5161    0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9678    0.3807    0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561    1.7138    0.7556 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5245    2.6469   -0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1894    4.0402    0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6906    2.2923   -1.4508 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2607   -0.0972    0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5731   -1.4158    0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9483   -1.8933    0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1966   -3.1037   -0.0212 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0169   -1.0330    0.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5390   -2.3071    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2290   -1.8426    0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1466   -2.7760   -0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4381   -3.9908   -0.3403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8077    3.7038    0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9604    3.5881   -1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5353    3.2127    0.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8927   -1.1495    0.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4260   -3.4889   -0.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0396   -4.2595   -0.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4211    4.2229    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7549    4.7834   -0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801    4.1494   -0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0473    0.6292    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1457   -0.6630    1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7604   -3.3557   -0.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  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
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 14 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 10  5  1  0
 25 13  1  0
 26  9  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 19 37  1  0
 23 38  1  0
 24 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Zondar	Kegg
Diacerhein	MeSH
Diacetyl-rhein	MeSH
Diacetylrhein	MeSH

Chemical Formula

C₁₉H₁₂O₈

Average Molecular Weight

368.297

Monoisotopic Molecular Weight

368.053217346

IUPAC Name

4,5-bis(acetyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Traditional Name

diacerein

CAS Registry Number

Not Available

SMILES

CC(=O)OC1=CC=CC2=C1C(=O)C1=C(OC(C)=O)C=C(C=C1C2=O)C(O)=O

InChI Identifier

InChI=1S/C19H12O8/c1-8(20)26-13-5-3-4-11-15(13)18(23)16-12(17(11)22)6-10(19(24)25)7-14(16)27-9(2)21/h3-7H,1-2H3,(H,24,25)

InChI Key

TYNLGDBUJLVSMA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthracenecarboxylic acids and derivatives

Direct Parent

Anthracenecarboxylic acids

Alternative Parents

Substituents

Anthracene carboxylic acid
9,10-anthraquinone
Anthraquinone
2-naphthalenecarboxylic acid
2-naphthalenecarboxylic acid or derivatives
Tricarboxylic acid or derivatives
Aryl ketone
Carboxylic acid ester
Ketone
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.14	ALOGPS
logP	1.79	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	124.04 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	90.67 m³·mol⁻¹	ChemAxon
Polarizability	35.37 Å³	ChemAxon
Number of Rings	3	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]+	177.076	30932474
DeepCCS	[M-H]-	174.718	30932474
DeepCCS	[M-2H]-	208.684	30932474
DeepCCS	[M+Na]+	183.912	30932474
AllCCS	[M+H]+	182.2	32859911
AllCCS	[M+H-H2O]+	179.2	32859911
AllCCS	[M+NH4]+	184.9	32859911
AllCCS	[M+Na]+	185.7	32859911
AllCCS	[M-H]-	184.0	32859911
AllCCS	[M+Na-2H]-	183.5	32859911
AllCCS	[M+HCOO]-	183.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diacerein	CC(=O)OC1=CC=CC2=C1C(=O)C1=C(OC(C)=O)C=C(C=C1C2=O)C(O)=O	4535.9	Standard polar	33892256
Diacerein	CC(=O)OC1=CC=CC2=C1C(=O)C1=C(OC(C)=O)C=C(C=C1C2=O)C(O)=O	2515.3	Standard non polar	33892256
Diacerein	CC(=O)OC1=CC=CC2=C1C(=O)C1=C(OC(C)=O)C=C(C=C1C2=O)C(O)=O	3033.7	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 - Diacerein GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-4298000000-d274ce99081d83e061c3	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacerein GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacerein GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diacerein 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 - Diacerein 10V, Positive-QTOF	splash10-016r-0009000000-282d8cafce2d1f0fd16e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacerein 20V, Positive-QTOF	splash10-004i-0029000000-13ca54008d3b77209390	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacerein 40V, Positive-QTOF	splash10-0a5l-4098000000-1596817dbfd6d27d7369	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacerein 10V, Negative-QTOF	splash10-00or-0009000000-93cd9bae57f36320b410	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacerein 20V, Negative-QTOF	splash10-00c0-0039000000-999aae5aaf77bc204eeb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacerein 40V, Negative-QTOF	splash10-001i-3092000000-f01fbcd2f6edab5d5611	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacerein 10V, Positive-QTOF	splash10-0a6r-0019000000-cd9a1d5055263f937e1d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacerein 20V, Positive-QTOF	splash10-052r-0089000000-ae1572e43665b9400637	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacerein 40V, Positive-QTOF	splash10-0a4r-0198000000-9a2410a44ad1863b075e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacerein 10V, Negative-QTOF	splash10-001i-0094000000-304a458d422904094fbd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacerein 20V, Negative-QTOF	splash10-00e9-0089000000-9ef0be1becf80f766b1a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diacerein 40V, Negative-QTOF	splash10-053r-0094000000-a52a5310c7bab4deb4cf	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

DB11994

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24456

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diacerein

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1665351

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 Diacerein (HMDB0251118)

MOL for HMDB0251118 (Diacerein)

3D MOL for HMDB0251118 (Diacerein)

3D SDF for HMDB0251118 (Diacerein)

3D-SDF for HMDB0251118 (Diacerein)

PDB for HMDB0251118 (Diacerein)

3D PDB for HMDB0251118 (Diacerein)

SMILES for HMDB0251118 (Diacerein)

INCHI for HMDB0251118 (Diacerein)

Structure for HMDB0251118 (Diacerein)

3D Structure for HMDB0251118 (Diacerein)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra