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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7)transporters (4) Show 11 proteins XML

enzymes (7)transporters (4) Show 11 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:59 UTC

HMDB ID

HMDB0015466

Secondary Accession Numbers

HMDB15466

Metabolite Identification

Common Name

Colchicine

Description

Colchicine is only found in individuals that have used or taken this drug. It is a major alkaloid from Colchicum autumnale L. and found also in other Colchicum species. Its primary therapeutic use is in the treatment of gout, but it has been used also in the therapy of familial Mediterranean fever (periodic disease). [PubChem]The precise mechanism of action has not been completely established. In patients with gout, colchicine apparently interrupts the cycle of monosodium urate crystal deposition in joint tissues and the resultant inflammatory response that initiates and sustains an acute attack. Colchicine decreases leukocyte chemotaxis and phagocytosis and inhibits the formation and release of a chemotactic glycoprotein that is produced during phagocytosis of urate crystals. Colchicine also inhibits urate crystal deposition, which is enhanced by a low pH in the tissues, probably by inhibiting oxidation of glucose and subsequent lactic acid production in leukocytes. Colchicine has no analgesic or antihyperuricemic activity. Colchicine inhibits microtubule assembly in various cells, including leukocytes, probably by binding to and interfering with polymerization of the microtubule subunit tubulin. Although some studies have found that this action probably does not contribute significantly to colchicine's antigout action, a recent in vitro study has shown that it may be at least partially involved.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 04191212172D          

 29 31  0  0  1  0            999 V2000
   -1.3595    1.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1638    1.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1638    0.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5218    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595   -0.1019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0015   -0.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595   -1.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1638   -1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8088   -1.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8088   -0.4327    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
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5521   -1.6156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474   -2.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7426   -3.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7593    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5843    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  3  2  0  0  0  0
  4  6  1  0  0  0  0
  1  2  1  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 15 16  1  0  0  0  0
  5 19  2  0  0  0  0
 14 15  2  0  0  0  0
 18 19  1  0  0  0  0
  3 14  1  0  0  0  0
 14  5  1  0  0  0  0
 13 20  1  0  0  0  0
 12 21  1  0  0  0  0
 11 22  1  0  0  0  0
 18 23  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
M  END

HMDB0015466
     RDKit          3D
Colchicine
 54 56  0  0  0  0  0  0  0  0999 V2000
    4.7732   -3.4071   -0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910   -2.1510    0.1599 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2880   -1.5233   -0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3470   -2.1245   -0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750   -1.4882   -1.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9568   -0.2274   -0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    0.3864    0.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5902    1.6000    0.8607 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9925    1.7191    2.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0607   -0.2741    0.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0654    0.2465    1.2989 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1944    0.0076    2.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024    0.6274   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829    1.8699   -0.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2645    3.0634   -0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6442    3.2768   -0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9747    4.5119    0.1233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9716    5.4506    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6774    2.3791   -0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7922    2.9225   -0.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6205    0.9813   -0.7449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5119    0.1757   -0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0561   -1.1291   -1.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0926   -1.4520   -0.2158 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4334   -1.7567   -0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4767   -2.0805    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7046   -1.7389   -1.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1197   -2.2939   -1.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1575   -2.1788   -1.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6879   -3.3199   -1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0937   -4.2058   -0.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8280   -3.7018   -0.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4949   -3.0979   -1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6179    1.2705    2.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0642    1.0783    2.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6521    2.7396    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0257    0.9444    3.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3492   -0.6795    2.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1479   -0.4908    2.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4098    1.8642   -1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3493    3.9439   -0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4584    5.7951   -0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4898    6.3061    0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1748    5.0293    1.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5888    0.5147   -0.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806   -1.0829   -2.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8648   -1.4670    0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0053   -1.1285    0.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0516   -2.4844    1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2636   -2.7509   -0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8894   -2.5252   -0.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6736   -3.1692   -1.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068   -3.2078   -2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164   -1.5674   -2.8552 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
 17 18  1  0
 16 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 23 28  1  0
 28 29  1  0
 10  3  1  0
 22 13  1  0
 29  5  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 14 40  1  0
 15 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 21 45  1  0
 23 46  1  0
 24 47  1  0
 26 48  1  0
 26 49  1  0
 26 50  1  0
 28 51  1  0
 28 52  1  0
 29 53  1  0
 29 54  1  0
M  END


  Mrv0541 04191212172D          

 29 31  0  0  1  0            999 V2000
   -1.3595    1.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1638    1.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1638    0.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5218    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595   -0.1019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0015   -0.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595   -1.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1638   -1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8088   -1.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8088   -0.4327    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
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5521   -1.6156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474   -2.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7426   -3.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7593    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5843    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  3  2  0  0  0  0
  4  6  1  0  0  0  0
  1  2  1  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 15 16  1  0  0  0  0
  5 19  2  0  0  0  0
 14 15  2  0  0  0  0
 18 19  1  0  0  0  0
  3 14  1  0  0  0  0
 14  5  1  0  0  0  0
 13 20  1  0  0  0  0
 12 21  1  0  0  0  0
 11 22  1  0  0  0  0
 18 23  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015466

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)

> <INCHI_KEY>
IAKHMKGGTNLKSZ-UHFFFAOYSA-N

> <FORMULA>
C22H25NO6

> <MOLECULAR_WEIGHT>
399.437

> <EXACT_MASS>
399.168187537

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
42.40842276748191

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-{3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.0²,⁷]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl}acetamide

> <ALOGPS_LOGP>
1.59

> <JCHEM_LOGP>
1.4619885703333333

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.72567746371771

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.057997338591893

> <JCHEM_PKA_STRONGEST_BASIC>
-0.0375340554539807

> <JCHEM_POLAR_SURFACE_AREA>
83.09

> <JCHEM_REFRACTIVITY>
111.37559999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
colchicine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015466
     RDKit          3D
Colchicine
 54 56  0  0  0  0  0  0  0  0999 V2000
    4.7732   -3.4071   -0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910   -2.1510    0.1599 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2880   -1.5233   -0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3470   -2.1245   -0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750   -1.4882   -1.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9568   -0.2274   -0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    0.3864    0.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5902    1.6000    0.8607 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9925    1.7191    2.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0607   -0.2741    0.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0654    0.2465    1.2989 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1944    0.0076    2.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024    0.6274   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829    1.8699   -0.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2645    3.0634   -0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6442    3.2768   -0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9747    4.5119    0.1233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9716    5.4506    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6774    2.3791   -0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7922    2.9225   -0.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6205    0.9813   -0.7449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5119    0.1757   -0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0561   -1.1291   -1.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0926   -1.4520   -0.2158 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4334   -1.7567   -0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4767   -2.0805    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7046   -1.7389   -1.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1197   -2.2939   -1.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1575   -2.1788   -1.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6879   -3.3199   -1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0937   -4.2058   -0.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8280   -3.7018   -0.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4949   -3.0979   -1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6179    1.2705    2.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0642    1.0783    2.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6521    2.7396    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0257    0.9444    3.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3492   -0.6795    2.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1479   -0.4908    2.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4098    1.8642   -1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3493    3.9439   -0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4584    5.7951   -0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4898    6.3061    0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1748    5.0293    1.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5888    0.5147   -0.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806   -1.0829   -2.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8648   -1.4670    0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0053   -1.1285    0.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0516   -2.4844    1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2636   -2.7509   -0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8894   -2.5252   -0.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6736   -3.1692   -1.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068   -3.2078   -2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164   -1.5674   -2.8552 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
 17 18  1  0
 16 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 23 28  1  0
 28 29  1  0
 10  3  1  0
 22 13  1  0
 29  5  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 14 40  1  0
 15 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 21 45  1  0
 23 46  1  0
 24 47  1  0
 26 48  1  0
 26 49  1  0
 26 50  1  0
 28 51  1  0
 28 52  1  0
 29 53  1  0
 29 54  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -2.538   3.270   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.039   2.927   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.039   0.153   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.707   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000  -1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.538  -0.190   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.869  -1.578   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.538  -2.965   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.039  -3.308   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.243  -2.348   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.243  -0.808   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.631  -3.016   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.382  -4.809   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.253  -5.857   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      -6.247   1.540   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      -7.017   2.874   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.247   4.207   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -8.557   2.874   0.000  0.00  0.00           O+0
CONECT    1    4    2                                                       
CONECT    2    3    1   10                                                  
CONECT    3    2    7   14                                                  
CONECT    4    1    6                                                       
CONECT    5    6   19   14                                                  
CONECT    6    4    5   26                                                  
CONECT    7    3    8   11                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9    2                                                       
CONECT   11    7   22                                                       
CONECT   12    8   21                                                       
CONECT   13    9   20                                                       
CONECT   14   15    3    5                                                  
CONECT   15   16   14                                                       
CONECT   16   17   15                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19   23                                                  
CONECT   19    5   18                                                       
CONECT   20   13                                                            
CONECT   21   12                                                            
CONECT   22   11                                                            
CONECT   23   18                                                            
CONECT   24   17   25                                                       
CONECT   25   24                                                            
CONECT   26    6   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

COMPND    HMDB0015466
HETATM    1  C1  UNL     1       4.773  -3.407  -0.407  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.491  -2.151   0.160  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.288  -1.523  -0.082  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.347  -2.125  -0.886  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.175  -1.488  -1.110  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.957  -0.227  -0.513  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.865   0.386   0.289  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.590   1.600   0.861  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.992   1.719   2.154  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.061  -0.274   0.509  1.00  0.00           C  
HETATM   11  O3  UNL     1       4.065   0.246   1.299  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.194   0.008   2.674  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.202   0.627  -0.722  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.383   1.870  -0.764  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.265   3.063  -0.561  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.644   3.277  -0.376  1.00  0.00           C  
HETATM   17  O4  UNL     1      -1.975   4.512   0.123  1.00  0.00           O  
HETATM   18  C14 UNL     1      -0.972   5.451   0.411  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.677   2.379  -0.645  1.00  0.00           C  
HETATM   20  O5  UNL     1      -3.792   2.923  -0.816  1.00  0.00           O  
HETATM   21  C16 UNL     1      -2.620   0.981  -0.745  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.512   0.176  -0.872  1.00  0.00           C  
HETATM   23  C18 UNL     1      -2.056  -1.129  -1.191  1.00  0.00           C  
HETATM   24  N1  UNL     1      -3.093  -1.452  -0.216  1.00  0.00           N  
HETATM   25  C19 UNL     1      -4.433  -1.757  -0.581  1.00  0.00           C  
HETATM   26  C20 UNL     1      -5.477  -2.081   0.395  1.00  0.00           C  
HETATM   27  O6  UNL     1      -4.705  -1.739  -1.810  1.00  0.00           O  
HETATM   28  C21 UNL     1      -1.120  -2.294  -1.167  1.00  0.00           C  
HETATM   29  C22 UNL     1       0.158  -2.179  -1.945  1.00  0.00           C  
HETATM   30  H1  UNL     1       4.688  -3.320  -1.510  1.00  0.00           H  
HETATM   31  H2  UNL     1       4.094  -4.206  -0.044  1.00  0.00           H  
HETATM   32  H3  UNL     1       5.828  -3.702  -0.178  1.00  0.00           H  
HETATM   33  H4  UNL     1       2.495  -3.098  -1.358  1.00  0.00           H  
HETATM   34  H5  UNL     1       1.618   1.271   2.922  1.00  0.00           H  
HETATM   35  H6  UNL     1       0.064   1.078   2.095  1.00  0.00           H  
HETATM   36  H7  UNL     1       0.652   2.740   2.336  1.00  0.00           H  
HETATM   37  H8  UNL     1       4.026   0.944   3.241  1.00  0.00           H  
HETATM   38  H9  UNL     1       3.349  -0.679   2.963  1.00  0.00           H  
HETATM   39  H10 UNL     1       5.148  -0.491   2.943  1.00  0.00           H  
HETATM   40  H11 UNL     1       1.410   1.864  -1.009  1.00  0.00           H  
HETATM   41  H12 UNL     1       0.349   3.944  -0.542  1.00  0.00           H  
HETATM   42  H13 UNL     1      -0.458   5.795  -0.522  1.00  0.00           H  
HETATM   43  H14 UNL     1      -1.490   6.306   0.912  1.00  0.00           H  
HETATM   44  H15 UNL     1      -0.175   5.029   1.077  1.00  0.00           H  
HETATM   45  H16 UNL     1      -3.589   0.515  -0.715  1.00  0.00           H  
HETATM   46  H17 UNL     1      -2.581  -1.083  -2.173  1.00  0.00           H  
HETATM   47  H18 UNL     1      -2.865  -1.467   0.807  1.00  0.00           H  
HETATM   48  H19 UNL     1      -6.005  -1.128   0.663  1.00  0.00           H  
HETATM   49  H20 UNL     1      -5.052  -2.484   1.325  1.00  0.00           H  
HETATM   50  H21 UNL     1      -6.264  -2.751  -0.004  1.00  0.00           H  
HETATM   51  H22 UNL     1      -0.889  -2.525  -0.112  1.00  0.00           H  
HETATM   52  H23 UNL     1      -1.674  -3.169  -1.566  1.00  0.00           H  
HETATM   53  H24 UNL     1       0.507  -3.208  -2.164  1.00  0.00           H  
HETATM   54  H25 UNL     1       0.016  -1.567  -2.855  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   33
CONECT    5    6    6   29
CONECT    6    7   13
CONECT    7    8   10   10
CONECT    8    9
CONECT    9   34   35   36
CONECT   10   11
CONECT   11   12
CONECT   12   37   38   39
CONECT   13   14   14   22
CONECT   14   15   40
CONECT   15   16   16   41
CONECT   16   17   19
CONECT   17   18
CONECT   18   42   43   44
CONECT   19   20   20   21
CONECT   21   22   22   45
CONECT   22   23
CONECT   23   24   28   46
CONECT   24   25   47
CONECT   25   26   27   27
CONECT   26   48   49   50
CONECT   28   29   51   52
CONECT   29   53   54
END

HMDB0015466
     RDKit          3D
Colchicine
 54 56  0  0  0  0  0  0  0  0999 V2000
    4.7732   -3.4071   -0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910   -2.1510    0.1599 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2880   -1.5233   -0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3470   -2.1245   -0.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750   -1.4882   -1.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9568   -0.2274   -0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    0.3864    0.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5902    1.6000    0.8607 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9925    1.7191    2.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0607   -0.2741    0.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0654    0.2465    1.2989 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1944    0.0076    2.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024    0.6274   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829    1.8699   -0.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2645    3.0634   -0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6442    3.2768   -0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9747    4.5119    0.1233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9716    5.4506    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6774    2.3791   -0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7922    2.9225   -0.8156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6205    0.9813   -0.7449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5119    0.1757   -0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0561   -1.1291   -1.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0926   -1.4520   -0.2158 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4334   -1.7567   -0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4767   -2.0805    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7046   -1.7389   -1.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1197   -2.2939   -1.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1575   -2.1788   -1.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6879   -3.3199   -1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0937   -4.2058   -0.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8280   -3.7018   -0.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4949   -3.0979   -1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6179    1.2705    2.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0642    1.0783    2.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6521    2.7396    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0257    0.9444    3.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3492   -0.6795    2.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1479   -0.4908    2.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4098    1.8642   -1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3493    3.9439   -0.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4584    5.7951   -0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4898    6.3061    0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1748    5.0293    1.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5888    0.5147   -0.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806   -1.0829   -2.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8648   -1.4670    0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0053   -1.1285    0.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0516   -2.4844    1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2636   -2.7509   -0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8894   -2.5252   -0.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6736   -3.1692   -1.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068   -3.2078   -2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0164   -1.5674   -2.8552 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
 17 18  1  0
 16 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 23 28  1  0
 28 29  1  0
 10  3  1  0
 22 13  1  0
 29  5  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 14 40  1  0
 15 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 21 45  1  0
 23 46  1  0
 24 47  1  0
 26 48  1  0
 26 49  1  0
 26 50  1  0
 28 51  1  0
 28 52  1  0
 29 53  1  0
 29 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Colchicin	HMDB
Colchicina	HMDB
Colchicinum	HMDB

Chemical Formula

C₂₂H₂₅NO₆

Average Molecular Weight

399.437

Monoisotopic Molecular Weight

399.168187537

IUPAC Name

N-{3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.0²,⁷]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl}acetamide

Traditional Name

colchicine

CAS Registry Number

64-86-8

SMILES

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

InChI Identifier

InChI=1S/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)

InChI Key

IAKHMKGGTNLKSZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropones. Tropones are compounds containing a tropone ring, which is a cycloheptatrienone ring bearing a ketone group.

Kingdom

Organic compounds

Super Class

Hydrocarbon derivatives

Class

Tropones

Sub Class

Not Available

Direct Parent

Tropones

Alternative Parents

Substituents

Anisole
Tropone
Alkyl aryl ether
Benzenoid
Cyclic ketone
Carboximidic acid
Carboximidic acid derivative
Ether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

aromatic ether (CHEBI:23359 )
alkaloid (CHEBI:23359 )
acetamides (CHEBI:23359 )
carbotricyclic compound (CHEBI:23359 )
an alkaloid (CPD-9785 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	156 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.028 g/L	Not Available
LogP	1.30	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.028 g/L	ALOGPS
logP	1.59	ALOGPS
logP	1.46	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	15.06	ChemAxon
pKa (Strongest Basic)	-0.038	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.09 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	111.38 m³·mol⁻¹	ChemAxon
Polarizability	42.41 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
DarkChem	[M+H]+	193.517	31661259
DarkChem	[M-H]-	193.8	31661259
DeepCCS	[M+H]+	193.235	30932474
DeepCCS	[M-H]-	190.877	30932474
DeepCCS	[M-2H]-	224.588	30932474
DeepCCS	[M+Na]+	199.817	30932474
AllCCS	[M+H]+	194.5	32859911
AllCCS	[M+H-H2O]+	191.9	32859911
AllCCS	[M+NH4]+	197.0	32859911
AllCCS	[M+Na]+	197.7	32859911
AllCCS	[M-H]-	199.4	32859911
AllCCS	[M+Na-2H]-	199.8	32859911
AllCCS	[M+HCOO]-	200.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Colchicine	COC1=CC2=C(C(OC)=C1OC)C1=CC=C(OC)C(=O)C=C1C(CC2)NC(C)=O	4733.2	Standard polar	33892256
Colchicine	COC1=CC2=C(C(OC)=C1OC)C1=CC=C(OC)C(=O)C=C1C(CC2)NC(C)=O	3364.6	Standard non polar	33892256
Colchicine	COC1=CC2=C(C(OC)=C1OC)C1=CC=C(OC)C(=O)C=C1C(CC2)NC(C)=O	3441.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Colchicine,1TMS,isomer #1	COC1=CC2=C(C3=CC=C(OC)C(=O)C=C3C(N(C(C)=O)[Si](C)(C)C)CC2)C(OC)=C1OC	3172.4	Semi standard non polar	33892256
Colchicine,1TMS,isomer #1	COC1=CC2=C(C3=CC=C(OC)C(=O)C=C3C(N(C(C)=O)[Si](C)(C)C)CC2)C(OC)=C1OC	3248.3	Standard non polar	33892256
Colchicine,1TMS,isomer #1	COC1=CC2=C(C3=CC=C(OC)C(=O)C=C3C(N(C(C)=O)[Si](C)(C)C)CC2)C(OC)=C1OC	4372.3	Standard polar	33892256
Colchicine,1TBDMS,isomer #1	COC1=CC2=C(C3=CC=C(OC)C(=O)C=C3C(N(C(C)=O)[Si](C)(C)C(C)(C)C)CC2)C(OC)=C1OC	3373.1	Semi standard non polar	33892256
Colchicine,1TBDMS,isomer #1	COC1=CC2=C(C3=CC=C(OC)C(=O)C=C3C(N(C(C)=O)[Si](C)(C)C(C)(C)C)CC2)C(OC)=C1OC	3460.0	Standard non polar	33892256
Colchicine,1TBDMS,isomer #1	COC1=CC2=C(C3=CC=C(OC)C(=O)C=C3C(N(C(C)=O)[Si](C)(C)C(C)(C)C)CC2)C(OC)=C1OC	4359.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Colchicine GC-MS (Non-derivatized) - 70eV, Positive	splash10-053u-1009000000-7a8d292bb6a5673c9d7c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Colchicine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Colchicine LC-ESI-QTOF , positive-QTOF	splash10-0udi-0000900000-c73c5a28a750cece607a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Colchicine LC-ESI-QTOF , positive-QTOF	splash10-0udi-0049400000-2a76bd81d41e1bc5925c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Colchicine LC-ESI-QTOF , positive-QTOF	splash10-0gba-0091000000-fb24bc910ffe7bd74811	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Colchicine 40V, Positive-QTOF	splash10-03gi-0096000000-1604b0f123208b25b949	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Colchicine 30V, Positive-QTOF	splash10-0zfr-0029400000-dc08a845d6fb327eec56	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Colchicine 10V, Positive-QTOF	splash10-0udi-0000900000-d360bbc1ca27b2e657d4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Colchicine 20V, Positive-QTOF	splash10-0udi-0000900000-44e9ac8566ca5c684603	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Colchicine 10V, Positive-QTOF	splash10-0udi-0000900000-9d973f7afeacb8db799d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Colchicine 50V, Positive-QTOF	splash10-0gc1-0192000000-dcb2736f710df3f17b01	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Colchicine 20V, Positive-QTOF	splash10-0udi-0049500000-27383218cdc648739307	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Colchicine 40V, Positive-QTOF	splash10-0gba-0091000000-fb24bc910ffe7bd74811	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Colchicine 10V, Positive-QTOF	splash10-0zfr-0009700000-00c1abf086f6716cac6b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Colchicine 20V, Positive-QTOF	splash10-0a4i-0009100000-4f6b3c625a6887981670	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Colchicine 40V, Positive-QTOF	splash10-05dl-0049000000-75fafbc5e28d11766c0c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Colchicine 10V, Negative-QTOF	splash10-0002-0009000000-cc76299babee13af8502	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Colchicine 20V, Negative-QTOF	splash10-0537-1009000000-247faa52698339d3e544	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Colchicine 40V, Negative-QTOF	splash10-0pi3-9077000000-eb1350fc19fa611668aa	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Colchicine 10V, Positive-QTOF	splash10-0udi-0001900000-958a463c4e2f7c3dd588	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Colchicine 20V, Positive-QTOF	splash10-0udl-0009500000-8181c90153beb9e9a4f5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Colchicine 40V, Positive-QTOF	splash10-052g-5079000000-81182c306cc4f86cf2c3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Colchicine 10V, Negative-QTOF	splash10-0002-0009000000-b40b49dac61f8e9864fa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Colchicine 20V, Negative-QTOF	splash10-0a4i-7009000000-666c5fffe6918e3020f7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Colchicine 40V, Negative-QTOF	splash10-0006-9007000000-7e1ec907f14345d7e992	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01394	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01394	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01394

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2731

KEGG Compound ID

C07592

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Colchicine

METLIN ID

Not Available

PubChem Compound

2833

PDB ID

Not Available

ChEBI ID

23359

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)

Download (PDF)

General References

Not Available

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Tubulin beta chain

General function:: Involved in structural molecule activity
Specific function:: Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha-chain
Gene Name:: TUBB
Uniprot ID:: P07437
Molecular weight:: 49670.5

References

Yee KW, Hagey A, Verstovsek S, Cortes J, Garcia-Manero G, O'Brien SM, Faderl S, Thomas D, Wierda W, Kornblau S, Ferrajoli A, Albitar M, McKeegan E, Grimm DR, Mueller T, Holley-Shanks RR, Sahelijo L, Gordon GB, Kantarjian HM, Giles FJ: Phase 1 study of ABT-751, a novel microtubule inhibitor, in patients with refractory hematologic malignancies. Clin Cancer Res. 2005 Sep 15;11(18):6615-24. [PubMed:16166440 ]
Acharya BR, Choudhury D, Das A, Chakrabarti G: Vitamin K3 disrupts the microtubule networks by binding to tubulin: a novel mechanism of its antiproliferative activity. Biochemistry. 2009 Jul 28;48(29):6963-74. doi: 10.1021/bi900152k. [PubMed:19527023 ]
Li CM, Lu Y, Ahn S, Narayanan R, Miller DD, Dalton JT: Competitive mass spectrometry binding assay for characterization of three binding sites of tubulin. J Mass Spectrom. 2010 Oct;45(10):1160-6. doi: 10.1002/jms.1804. [PubMed:20814887 ]
Cerquaglia C, Diaco M, Nucera G, La Regina M, Montalto M, Manna R: Pharmacological and clinical basis of treatment of Familial Mediterranean Fever (FMF) with colchicine or analogues: an update. Curr Drug Targets Inflamm Allergy. 2005 Feb;4(1):117-24. [PubMed:15720245 ]

Enzyme Details

7. Tubulin beta-1 chain

General function:: Involved in structural molecule activity
Specific function:: Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha-chain
Gene Name:: TUBB1
Uniprot ID:: Q9H4B7
Molecular weight:: 50326.6

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Acharya BR, Choudhury D, Das A, Chakrabarti G: Vitamin K3 disrupts the microtubule networks by binding to tubulin: a novel mechanism of its antiproliferative activity. Biochemistry. 2009 Jul 28;48(29):6963-74. doi: 10.1021/bi900152k. [PubMed:19527023 ]
Li CM, Lu Y, Ahn S, Narayanan R, Miller DD, Dalton JT: Competitive mass spectrometry binding assay for characterization of three binding sites of tubulin. J Mass Spectrom. 2010 Oct;45(10):1160-6. doi: 10.1002/jms.1804. [PubMed:20814887 ]
Finkelstein Y, Aks SE, Hutson JR, Juurlink DN, Nguyen P, Dubnov-Raz G, Pollak U, Koren G, Bentur Y: Colchicine poisoning: the dark side of an ancient drug. Clin Toxicol (Phila). 2010 Jun;48(5):407-14. doi: 10.3109/15563650.2010.495348. [PubMed:20586571 ]
Cerquaglia C, Diaco M, Nucera G, La Regina M, Montalto M, Manna R: Pharmacological and clinical basis of treatment of Familial Mediterranean Fever (FMF) with colchicine or analogues: an update. Curr Drug Targets Inflamm Allergy. 2005 Feb;4(1):117-24. [PubMed:15720245 ]

Transporters

Enzyme Details

1. Multidrug resistance-associated protein 1

General function:: Involved in ATP binding
Specific function:: Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:: ABCC1
Uniprot ID:: P33527
Molecular weight:: 171589.5

References

Stride BD, Grant CE, Loe DW, Hipfner DR, Cole SP, Deeley RG: Pharmacological characterization of the murine and human orthologs of multidrug-resistance protein in transfected human embryonic kidney cells. Mol Pharmacol. 1997 Sep;52(3):344-53. [PubMed:9281595 ]

Enzyme Details

2. Multidrug resistance protein 3

General function:: Involved in ATP binding
Specific function:: Mediates ATP-dependent export of organic anions and drugs from the cytoplasm. Hydrolyzes ATP with low efficiency. Human MDR3 is not capable of conferring drug resistance. Mediates the translocation of phosphatidylcholine across the canalicular membrane of the hepatocyte
Gene Name:: ABCB4
Uniprot ID:: P21439
Molecular weight:: 141521.8

References

Vollrath V, Wielandt AM, Acuna C, Duarte I, Andrade L, Chianale J: Effect of colchicine and heat shock on multidrug resistance gene and P-glycoprotein expression in rat liver. J Hepatol. 1994 Nov;21(5):754-63. [PubMed:7890890 ]

Enzyme Details

3. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]
Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389 ]
Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]
Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [PubMed:12948019 ]
Ambudkar SV, Lelong IH, Zhang J, Cardarelli CO, Gottesman MM, Pastan I: Partial purification and reconstitution of the human multidrug-resistance pump: characterization of the drug-stimulatable ATP hydrolysis. Proc Natl Acad Sci U S A. 1992 Sep 15;89(18):8472-6. [PubMed:1356264 ]
Bebawy M, Morris MB, Roufogalis BD: A continuous fluorescence assay for the study of P-glycoprotein-mediated drug efflux using inside-out membrane vesicles. Anal Biochem. 1999 Mar 15;268(2):270-7. [PubMed:10075817 ]
Kuo CC, Hsieh HP, Pan WY, Chen CP, Liou JP, Lee SJ, Chang YL, Chen LT, Chen CT, Chang JY: BPR0L075, a novel synthetic indole compound with antimitotic activity in human cancer cells, exerts effective antitumoral activity in vivo. Cancer Res. 2004 Jul 1;64(13):4621-8. [PubMed:15231674 ]
Tiwari AK, Sodani K, Wang SR, Kuang YH, Ashby CR Jr, Chen X, Chen ZS: Nilotinib (AMN107, Tasigna) reverses multidrug resistance by inhibiting the activity of the ABCB1/Pgp and ABCG2/BCRP/MXR transporters. Biochem Pharmacol. 2009 Jul 15;78(2):153-61. doi: 10.1016/j.bcp.2009.04.002. Epub 2009 Apr 11. [PubMed:19427995 ]

Enzyme Details

4. Solute carrier family 22 member 3

General function:: Involved in transmembrane transport
Specific function:: Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:: SLC22A3
Uniprot ID:: O75751
Molecular weight:: 61279.5

References

Grundemann D, Schechinger B, Rappold GA, Schomig E: Molecular identification of the corticosterone-sensitive extraneuronal catecholamine transporter. Nat Neurosci. 1998 Sep;1(5):349-51. [PubMed:10196521 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for Colchicine (HMDB0015466)

MOL for HMDB0015466 (Colchicine)

3D MOL for HMDB0015466 (Colchicine)

3D SDF for HMDB0015466 (Colchicine)

3D-SDF for HMDB0015466 (Colchicine)

PDB for HMDB0015466 (Colchicine)

3D PDB for HMDB0015466 (Colchicine)

SMILES for HMDB0015466 (Colchicine)

INCHI for HMDB0015466 (Colchicine)

Structure for HMDB0015466 (Colchicine)

3D Structure for HMDB0015466 (Colchicine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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Transporters

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