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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:44:26 UTC

Update Date

2022-11-23 22:29:21 UTC

HMDB ID

HMDB0259241

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Trimethylcolchicinic acid

Description

10-amino-14-hydroxy-3,4,5-trimethoxytricyclo[9.5.0.0²,⁷]hexadeca-1(16),2,4,6,11,14-hexaen-13-one belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2. Based on a literature review very few articles have been published on 10-amino-14-hydroxy-3,4,5-trimethoxytricyclo[9.5.0.0²,⁷]hexadeca-1(16),2,4,6,11,14-hexaen-13-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). Trimethylcolchicinic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Trimethylcolchicinic 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

HMDB0259241
     RDKit          3D
TRIMETHYLCOLCHICINIC ACID
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.9035   -1.8804   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3185   -0.6127   -0.3016 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9567   -0.4989   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1565   -1.6263   -0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8001   -1.5135    0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2919   -0.2017    0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0418    0.9230    0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4536    2.1719    0.2178 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0298    2.8317   -0.9755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4001    0.7717   -0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1631    1.9242   -0.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4568    2.5936   -1.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0971    0.1283    0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9538    1.2290    1.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9355    2.1546    1.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938    2.1053    1.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0441    3.2263    1.5548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9670    1.0783    0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2312    1.2150    0.4970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4934   -0.1081    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2250   -0.5614    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2154   -1.9736   -0.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5540   -2.4651   -0.5249 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3534   -2.7684    0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1016   -2.8031    0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9741   -1.7884   -0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8422   -2.4466    0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3800   -2.5150   -1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6182   -2.6173   -0.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9487    3.2895   -0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126    2.1363   -1.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660    3.6455   -1.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7241    2.3218   -2.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4184    3.6943   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4975    2.3556   -1.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0133    1.2950    1.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454    3.0292    2.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5939    4.0041    2.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1783   -0.7575   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7005   -1.9187   -1.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8699   -2.5022   -1.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6780   -3.4168   -0.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7088   -3.8392    0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5844   -2.4936    1.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3127   -3.4555   -0.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5650   -3.3603    1.1206 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  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 10  3  1  0
 21 13  1  0
 25  5  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 15 37  1  0
 17 38  1  0
 20 39  1  0
 22 40  1  0
 23 41  1  0
 23 42  1  0
 24 43  1  0
 24 44  1  0
 25 45  1  0
 25 46  1  0
M  END

  Mrv1533004161504122D          

 25 27  0  0  0  0            999 V2000
    0.9119   -2.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1867   -1.5597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9977   -1.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0836   -0.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2393    0.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9698    0.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250    0.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3519    0.9180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9362   -0.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7607   -0.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2970   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0945   -0.8031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1413   -1.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4108   -2.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6556   -1.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4444   -1.0782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6199   -1.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3451   -1.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8814   -2.5115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6067   -3.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5341   -2.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2593   -2.8135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4483   -2.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8037   -2.3163    0.0000 O   0  0  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  2  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259241

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(OC)=C1OC)C1=CC=C(O)C(=O)C=C1C(N)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO5/c1-23-16-8-10-4-6-13(20)12-9-15(22)14(21)7-5-11(12)17(10)19(25-3)18(16)24-2/h5,7-9,13H,4,6,20H2,1-3H3,(H,21,22)

> <INCHI_KEY>
IRVWPZRYDQROLU-UHFFFAOYSA-N

> <FORMULA>
C19H21NO5

> <MOLECULAR_WEIGHT>
343.379

> <EXACT_MASS>
343.14197278

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.91423003870009

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-amino-14-hydroxy-3,4,5-trimethoxytricyclo[9.5.0.0²,⁷]hexadeca-1(16),2(7),3,5,11,14-hexaen-13-one

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
1.3165120353413093

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.90230193491454

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.38168046566943

> <JCHEM_PKA_STRONGEST_BASIC>
10.608268635707281

> <JCHEM_POLAR_SURFACE_AREA>
91.01

> <JCHEM_REFRACTIVITY>
97.18059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethylcolchicinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259241
     RDKit          3D
TRIMETHYLCOLCHICINIC ACID
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.9035   -1.8804   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3185   -0.6127   -0.3016 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9567   -0.4989   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1565   -1.6263   -0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8001   -1.5135    0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2919   -0.2017    0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0418    0.9230    0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4536    2.1719    0.2178 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0298    2.8317   -0.9755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4001    0.7717   -0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1631    1.9242   -0.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4568    2.5936   -1.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0971    0.1283    0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9538    1.2290    1.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9355    2.1546    1.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938    2.1053    1.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0441    3.2263    1.5548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9670    1.0783    0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2312    1.2150    0.4970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4934   -0.1081    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2250   -0.5614    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2154   -1.9736   -0.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5540   -2.4651   -0.5249 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3534   -2.7684    0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1016   -2.8031    0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9741   -1.7884   -0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8422   -2.4466    0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3800   -2.5150   -1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6182   -2.6173   -0.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9487    3.2895   -0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126    2.1363   -1.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660    3.6455   -1.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7241    2.3218   -2.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4184    3.6943   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4975    2.3556   -1.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0133    1.2950    1.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454    3.0292    2.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5939    4.0041    2.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1783   -0.7575   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7005   -1.9187   -1.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8699   -2.5022   -1.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6780   -3.4168   -0.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7088   -3.8392    0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5844   -2.4936    1.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3127   -3.4555   -0.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5650   -3.3603    1.1206 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  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 10  3  1  0
 21 13  1  0
 25  5  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 15 37  1  0
 17 38  1  0
 20 39  1  0
 22 40  1  0
 23 41  1  0
 23 42  1  0
 24 43  1  0
 24 44  1  0
 25 45  1  0
 25 46  1  0
M  END

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       1.702  -4.364   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.215  -2.911   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.729  -2.630   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.242  -1.177   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.756  -0.896   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.047   0.617   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.410   1.332   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.820   0.712   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       9.990   1.714   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       9.214  -0.776   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.753  -0.723   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.754  -1.893   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.243  -1.499   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.464  -3.406   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.100  -4.121   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.690  -3.501   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.296  -2.013   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.757  -2.066   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.244  -3.518   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.245  -4.688   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.732  -6.140   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.730  -3.800   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.217  -5.252   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.703  -5.534   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.700  -4.324   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   10   18                                                  
CONECT   18   17    5   19                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19    3   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   14                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0259241
HETATM    1  C1  UNL     1       4.903  -1.880  -0.384  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.318  -0.613  -0.302  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.957  -0.499  -0.112  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.157  -1.626  -0.002  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.800  -1.514   0.189  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.292  -0.202   0.264  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.042   0.923   0.155  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.454   2.172   0.218  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.030   2.832  -0.976  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.400   0.772  -0.034  1.00  0.00           C  
HETATM   11  O3  UNL     1       3.163   1.924  -0.139  1.00  0.00           O  
HETATM   12  C9  UNL     1       3.457   2.594  -1.326  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.097   0.128   0.546  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.954   1.229   1.362  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.935   2.155   1.600  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.294   2.105   1.238  1.00  0.00           C  
HETATM   17  O4  UNL     1      -4.044   3.226   1.555  1.00  0.00           O  
HETATM   18  C14 UNL     1      -3.967   1.078   0.607  1.00  0.00           C  
HETATM   19  O5  UNL     1      -5.231   1.215   0.497  1.00  0.00           O  
HETATM   20  C15 UNL     1      -3.493  -0.108   0.058  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.225  -0.561   0.104  1.00  0.00           C  
HETATM   22  C17 UNL     1      -2.215  -1.974  -0.397  1.00  0.00           C  
HETATM   23  N1  UNL     1      -3.554  -2.465  -0.525  1.00  0.00           N  
HETATM   24  C18 UNL     1      -1.353  -2.768   0.521  1.00  0.00           C  
HETATM   25  C19 UNL     1       0.102  -2.803   0.253  1.00  0.00           C  
HETATM   26  H1  UNL     1       5.974  -1.788  -0.638  1.00  0.00           H  
HETATM   27  H2  UNL     1       4.842  -2.447   0.586  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.380  -2.515  -1.133  1.00  0.00           H  
HETATM   29  H4  UNL     1       2.618  -2.617  -0.069  1.00  0.00           H  
HETATM   30  H5  UNL     1      -0.949   3.290  -0.854  1.00  0.00           H  
HETATM   31  H6  UNL     1       0.113   2.136  -1.831  1.00  0.00           H  
HETATM   32  H7  UNL     1       0.766   3.646  -1.160  1.00  0.00           H  
HETATM   33  H8  UNL     1       2.724   2.322  -2.124  1.00  0.00           H  
HETATM   34  H9  UNL     1       3.418   3.694  -1.129  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.498   2.356  -1.610  1.00  0.00           H  
HETATM   36  H11 UNL     1      -0.013   1.295   1.834  1.00  0.00           H  
HETATM   37  H12 UNL     1      -1.645   3.029   2.126  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.594   4.004   2.018  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.178  -0.758  -0.464  1.00  0.00           H  
HETATM   40  H15 UNL     1      -1.701  -1.919  -1.397  1.00  0.00           H  
HETATM   41  H16 UNL     1      -3.870  -2.502  -1.538  1.00  0.00           H  
HETATM   42  H17 UNL     1      -3.678  -3.417  -0.098  1.00  0.00           H  
HETATM   43  H18 UNL     1      -1.709  -3.839   0.439  1.00  0.00           H  
HETATM   44  H19 UNL     1      -1.584  -2.494   1.573  1.00  0.00           H  
HETATM   45  H20 UNL     1       0.313  -3.455  -0.623  1.00  0.00           H  
HETATM   46  H21 UNL     1       0.565  -3.360   1.121  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   29
CONECT    5    6    6   25
CONECT    6    7   13
CONECT    7    8   10   10
CONECT    8    9
CONECT    9   30   31   32
CONECT   10   11
CONECT   11   12
CONECT   12   33   34   35
CONECT   13   14   14   21
CONECT   14   15   36
CONECT   15   16   16   37
CONECT   16   17   18
CONECT   17   38
CONECT   18   19   19   20
CONECT   20   21   21   39
CONECT   21   22
CONECT   22   23   24   40
CONECT   23   41   42
CONECT   24   25   43   44
CONECT   25   45   46
END

HMDB0259241
     RDKit          3D
TRIMETHYLCOLCHICINIC ACID
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.9035   -1.8804   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3185   -0.6127   -0.3016 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9567   -0.4989   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1565   -1.6263   -0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8001   -1.5135    0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2919   -0.2017    0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0418    0.9230    0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4536    2.1719    0.2178 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0298    2.8317   -0.9755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4001    0.7717   -0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1631    1.9242   -0.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4568    2.5936   -1.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0971    0.1283    0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9538    1.2290    1.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9355    2.1546    1.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938    2.1053    1.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0441    3.2263    1.5548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9670    1.0783    0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2312    1.2150    0.4970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4934   -0.1081    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2250   -0.5614    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2154   -1.9736   -0.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5540   -2.4651   -0.5249 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3534   -2.7684    0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1016   -2.8031    0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9741   -1.7884   -0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8422   -2.4466    0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3800   -2.5150   -1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6182   -2.6173   -0.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9487    3.2895   -0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126    2.1363   -1.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660    3.6455   -1.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7241    2.3218   -2.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4184    3.6943   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4975    2.3556   -1.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0133    1.2950    1.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454    3.0292    2.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5939    4.0041    2.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1783   -0.7575   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7005   -1.9187   -1.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8699   -2.5022   -1.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6780   -3.4168   -0.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7088   -3.8392    0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5844   -2.4936    1.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3127   -3.4555   -0.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5650   -3.3603    1.1206 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  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 10  3  1  0
 21 13  1  0
 25  5  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 15 37  1  0
 17 38  1  0
 20 39  1  0
 22 40  1  0
 23 41  1  0
 23 42  1  0
 24 43  1  0
 24 44  1  0
 25 45  1  0
 25 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₂₁NO₅

Average Molecular Weight

343.379

Monoisotopic Molecular Weight

343.14197278

IUPAC Name

10-amino-14-hydroxy-3,4,5-trimethoxytricyclo[9.5.0.0²,⁷]hexadeca-1(16),2(7),3,5,11,14-hexaen-13-one

Traditional Name

trimethylcolchicinic acid

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(OC)=C1OC)C1=CC=C(O)C(=O)C=C1C(N)CC2

InChI Identifier

InChI=1S/C19H21NO5/c1-23-16-8-10-4-6-13(20)12-9-15(22)14(21)7-5-11(12)17(10)19(25-3)18(16)24-2/h5,7-9,13H,4,6,20H2,1-3H3,(H,21,22)

InChI Key

IRVWPZRYDQROLU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2.

Kingdom

Organic compounds

Super Class

Hydrocarbon derivatives

Class

Tropones

Sub Class

Tropolones

Direct Parent

Tropolones

Alternative Parents

Substituents

Tropolone
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Cyclic ketone
Ether
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Amine
Organic oxide
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)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.99	ALOGPS
logP	1.32	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.38	ChemAxon
pKa (Strongest Basic)	10.61	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.01 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.18 m³·mol⁻¹	ChemAxon
Polarizability	35.91 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]+	183.707	30932474
DeepCCS	[M-H]-	181.066	30932474
DeepCCS	[M-2H]-	215.641	30932474
DeepCCS	[M+Na]+	190.869	30932474
AllCCS	[M+H]+	181.3	32859911
AllCCS	[M+H-H2O]+	178.5	32859911
AllCCS	[M+NH4]+	184.0	32859911
AllCCS	[M+Na]+	184.8	32859911
AllCCS	[M-H]-	181.6	32859911
AllCCS	[M+Na-2H]-	181.5	32859911
AllCCS	[M+HCOO]-	181.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
TRIMETHYLCOLCHICINIC ACID	COC1=CC2=C(C(OC)=C1OC)C1=CC=C(O)C(=O)C=C1C(N)CC2	4284.9	Standard polar	33892256
TRIMETHYLCOLCHICINIC ACID	COC1=CC2=C(C(OC)=C1OC)C1=CC=C(O)C(=O)C=C1C(N)CC2	3066.8	Standard non polar	33892256
TRIMETHYLCOLCHICINIC ACID	COC1=CC2=C(C(OC)=C1OC)C1=CC=C(O)C(=O)C=C1C(N)CC2	3092.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
TRIMETHYLCOLCHICINIC ACID,2TMS,isomer #1	COC1=CC2=C(C3=CC=C(O[Si](C)(C)C)C(=O)C=C3C(N[Si](C)(C)C)CC2)C(OC)=C1OC	3096.6	Semi standard non polar	33892256
TRIMETHYLCOLCHICINIC ACID,2TMS,isomer #1	COC1=CC2=C(C3=CC=C(O[Si](C)(C)C)C(=O)C=C3C(N[Si](C)(C)C)CC2)C(OC)=C1OC	3098.4	Standard non polar	33892256
TRIMETHYLCOLCHICINIC ACID,2TMS,isomer #1	COC1=CC2=C(C3=CC=C(O[Si](C)(C)C)C(=O)C=C3C(N[Si](C)(C)C)CC2)C(OC)=C1OC	3766.0	Standard polar	33892256
TRIMETHYLCOLCHICINIC ACID,2TMS,isomer #2	COC1=CC2=C(C3=CC=C(O)C(=O)C=C3C(N([Si](C)(C)C)[Si](C)(C)C)CC2)C(OC)=C1OC	3114.7	Semi standard non polar	33892256
TRIMETHYLCOLCHICINIC ACID,2TMS,isomer #2	COC1=CC2=C(C3=CC=C(O)C(=O)C=C3C(N([Si](C)(C)C)[Si](C)(C)C)CC2)C(OC)=C1OC	3130.6	Standard non polar	33892256
TRIMETHYLCOLCHICINIC ACID,2TMS,isomer #2	COC1=CC2=C(C3=CC=C(O)C(=O)C=C3C(N([Si](C)(C)C)[Si](C)(C)C)CC2)C(OC)=C1OC	3967.9	Standard polar	33892256
TRIMETHYLCOLCHICINIC ACID,3TMS,isomer #1	COC1=CC2=C(C3=CC=C(O[Si](C)(C)C)C(=O)C=C3C(N([Si](C)(C)C)[Si](C)(C)C)CC2)C(OC)=C1OC	3089.0	Semi standard non polar	33892256
TRIMETHYLCOLCHICINIC ACID,3TMS,isomer #1	COC1=CC2=C(C3=CC=C(O[Si](C)(C)C)C(=O)C=C3C(N([Si](C)(C)C)[Si](C)(C)C)CC2)C(OC)=C1OC	3227.4	Standard non polar	33892256
TRIMETHYLCOLCHICINIC ACID,3TMS,isomer #1	COC1=CC2=C(C3=CC=C(O[Si](C)(C)C)C(=O)C=C3C(N([Si](C)(C)C)[Si](C)(C)C)CC2)C(OC)=C1OC	3614.2	Standard polar	33892256
TRIMETHYLCOLCHICINIC ACID,2TBDMS,isomer #1	COC1=CC2=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(=O)C=C3C(N[Si](C)(C)C(C)(C)C)CC2)C(OC)=C1OC	3468.8	Semi standard non polar	33892256
TRIMETHYLCOLCHICINIC ACID,2TBDMS,isomer #1	COC1=CC2=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(=O)C=C3C(N[Si](C)(C)C(C)(C)C)CC2)C(OC)=C1OC	3535.4	Standard non polar	33892256
TRIMETHYLCOLCHICINIC ACID,2TBDMS,isomer #1	COC1=CC2=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(=O)C=C3C(N[Si](C)(C)C(C)(C)C)CC2)C(OC)=C1OC	3890.2	Standard polar	33892256
TRIMETHYLCOLCHICINIC ACID,2TBDMS,isomer #2	COC1=CC2=C(C3=CC=C(O)C(=O)C=C3C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC2)C(OC)=C1OC	3532.7	Semi standard non polar	33892256
TRIMETHYLCOLCHICINIC ACID,2TBDMS,isomer #2	COC1=CC2=C(C3=CC=C(O)C(=O)C=C3C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC2)C(OC)=C1OC	3531.1	Standard non polar	33892256
TRIMETHYLCOLCHICINIC ACID,2TBDMS,isomer #2	COC1=CC2=C(C3=CC=C(O)C(=O)C=C3C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC2)C(OC)=C1OC	3980.2	Standard polar	33892256
TRIMETHYLCOLCHICINIC ACID,3TBDMS,isomer #1	COC1=CC2=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(=O)C=C3C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC2)C(OC)=C1OC	3695.2	Semi standard non polar	33892256
TRIMETHYLCOLCHICINIC ACID,3TBDMS,isomer #1	COC1=CC2=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(=O)C=C3C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC2)C(OC)=C1OC	3815.6	Standard non polar	33892256
TRIMETHYLCOLCHICINIC ACID,3TBDMS,isomer #1	COC1=CC2=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(=O)C=C3C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC2)C(OC)=C1OC	3795.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethylcolchicinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0059000000-30d13c3148f03968051d	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethylcolchicinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethylcolchicinic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethylcolchicinic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethylcolchicinic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethylcolchicinic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	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

17937

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

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

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 Trimethylcolchicinic acid (HMDB0259241)

MOL for HMDB0259241 (Trimethylcolchicinic acid)

3D MOL for HMDB0259241 (Trimethylcolchicinic acid)

3D SDF for HMDB0259241 (Trimethylcolchicinic acid)

3D-SDF for HMDB0259241 (Trimethylcolchicinic acid)

PDB for HMDB0259241 (Trimethylcolchicinic acid)

3D PDB for HMDB0259241 (Trimethylcolchicinic acid)

SMILES for HMDB0259241 (Trimethylcolchicinic acid)

INCHI for HMDB0259241 (Trimethylcolchicinic acid)

Structure for HMDB0259241 (Trimethylcolchicinic acid)

3D Structure for HMDB0259241 (Trimethylcolchicinic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra