Colchicine (CED0001466)

Record Information

Version

1.0

Creation Date

2014-08-29 04:49:18 UTC

Update Date

2026-05-14 17:00:04 UTC

SynCED ID

CED0001466

Secondary Accession Numbers

CHEM002980
T3D4020

Identification

Common Name

Colchicine

Class

Small Molecule

Description

Colchicine is an exogenous solid with the formula C22H25NO6 and an average molecular weight of 399.44 g/mol. Colchicine belongs to the tropones, a class of hydrocarbon derivatives within the organic compounds. This compound acts as a biological mutagen and targets nine proteins, including the Tubulin beta chain (TUBB), Tubulin beta-1 chain (TUBB1), Protein c-Fos (FOS), and Cellular tumor antigen p53 (TP53). The compound is used in medical devices and antigout preparations for the treatment of gout and familial Mediterranean fever (periodic disease). In patients with gout, it interrupts the cycle of monosodium urate crystal deposition in joint tissues and the subsequent inflammatory response. It inhibits the formation and release of a chemotactic glycoprotein produced during phagocytosis of urate crystals, while decreasing leukocyte chemotaxis and phagocytosis. Furthermore, colchicine inhibits urate crystal deposition, likely by inhibiting glucose oxidation and lactic acid production in leukocytes. It inhibits microtubule assembly in various cells, including leukocytes, by interfering with the polymerization of the microtubule subunit tubulin. Colchicine possesses no antihyperuricemic or analgesic activity. Colchicine is found in or released from 15 recorded sources, including lubricants, drinking water, food packaging, synthetic textiles, carpets and rugs, and healthcare, pharmaceuticals & veterinary products. It is also associated with electrical and electronic equipment such as capacitors, batteries, wires and cables, printed circuit boards, and cell phones. Recorded exposure routes include oral, inhalation, touch, and topical application.

Contaminant Type

Drug
Ester
Ether
Gout Suppressant
Human Neurotoxin
Metabolite
Natural Compound
Organic Compound
PFAS
Phytotoxin
Plant Toxin
Tubulin Modulator

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Colchicin	HMDB
Colchicina	HMDB
Colchicinum	HMDB

Chemical Formula

C₂₂H₂₅NO₆

Average Molecular Mass

399.437 g/mol

Monoisotopic Mass

399.168 g/mol

CAS Registry Number

64-86-8

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

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

mutagen ?A chemical substance that alters the genetic material of an organism, and increases the frequency of mutations above the naturally-occuring rate

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	156°C
Boiling Point	Not Available
Solubility	4.5E+004 mg/L (at 25°C)

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-053u-1009000000-7a8d292bb6a5673c9d7c	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0000900000-c73c5a28a750cece607a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0049400000-2a76bd81d41e1bc5925c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gba-0091000000-fb24bc910ffe7bd74811	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03gi-0096000000-1604b0f123208b25b949	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0zfr-0029400000-dc08a845d6fb327eec56	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0000900000-d360bbc1ca27b2e657d4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0000900000-44e9ac8566ca5c684603	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0000900000-9d973f7afeacb8db799d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gc1-0192000000-dcb2736f710df3f17b01	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0049500000-27383218cdc648739307	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gba-0091000000-fb24bc910ffe7bd74811	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zfr-0009700000-00c1abf086f6716cac6b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0009100000-4f6b3c625a6887981670	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05dl-0049000000-75fafbc5e28d11766c0c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0009000000-cc76299babee13af8502	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0537-1009000000-247faa52698339d3e544	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pi3-9077000000-eb1350fc19fa611668aa	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0001900000-958a463c4e2f7c3dd588	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udl-0009500000-8181c90153beb9e9a4f5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052g-5079000000-81182c306cc4f86cf2c3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0009000000-b40b49dac61f8e9864fa	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-7009000000-666c5fffe6918e3020f7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9007000000-7e1ec907f14345d7e992	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
691.0 Log mg/kg [390:1200]	Rat	LD50	oral	predicted	Not Available	Not Available
1.0 mg/kg-day	Mouse	LOEL	injection	experimental	Not Available	ECOTOX - EPA ORD
1.5 mg/kg-day	Mouse	LOEL	injection	experimental	Not Available	ECOTOX - EPA ORD
1.0 mg/kg-day	Mouse	LOEL	injection	experimental	Not Available	ECOTOX - EPA ORD
1.5 mg/kg-day	Mouse	LOEL	injection	experimental	Not Available	ECOTOX - EPA ORD
2.0 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
2.0 mg/kg-day	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
6.0 mg/kg-day	Rat	NOEL	oral	experimental	Not Available	ECOTOX - EPA ORD
4.0 mg/kg-day	Rat	LOEL	oral	experimental	Not Available	ECOTOX - EPA ORD

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

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.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000007	Pesticides?Pesticides are synthetic chemicals designed to prevent, destroy, or control pests that threaten crops and agricultural productivity.	Agriculture & land management	Not Available
CEDs000115	Drinking water?Drinking water can be a medium for synthetic chemical contamination, often originating from various industrial processes and agricultural practices.	Drinking water & water supply	Not Available
CEDs000120	Wires and cables?Wires and cables are integral components in the transmission of electrical power and signals.	Electrical & Electronic Equipment	Not Available
CEDs000121	Printed circuit boards?Printed circuit boards (PCBs) are essential components in the manufacturing of electronic devices, serving as the backbone for electrical connections and circuit pathways.	Electrical & Electronic Equipment	Not Available
CEDs000125	Batteries?Batteries are devices that store and release electrical energy through electrochemical reactions.	Electrical & Electronic Equipment	Not Available
CEDs000130	Semiconductors?Semiconductors are materials that possess electrical conductivity between that of conductors and insulators, making them essential for various electronic applications, including transistors, diodes, and integrated circuits.	Electrical & Electronic Equipment	Not Available
CEDs000138	Lubricants?Lubricants are synthetic or petroleum-derived substances used to reduce friction between surfaces in machinery and equipment, enhancing operational efficiency and longevity.	Energy, oil & gas	Not Available
CEDs000147	Food packaging?Food packaging often utilizes synthetic chemicals, such as plastics and coatings, to enhance durability, moisture resistance, and shelf life.	Food, food processing & cookware	Not Available
CEDs000174	Lubricants?Lubricants are synthetic or petroleum-based substances used to reduce friction and wear between moving parts in machinery and equipment.	Industrial manufacturing & chemical processing	Not Available
CEDs000234	Medical devices?Medical devices often incorporate synthetic chemicals in their manufacturing processes, which can contribute to contamination in healthcare settings.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000366	Antigout preparations?Antigout preparations are pharmaceutical formulations used to manage gout, a type of arthritis characterized by the accumulation of uric acid crystals in the joints.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000451	Carpets and Rugs?Carpets and rugs are commonly manufactured using synthetic fibers such as nylon, polyester, and polypropylene, which can be derived from petrochemical sources.	Textiles, leather & furnishings	Not Available
CEDs000454	Synthetic textiles?Synthetic textiles are materials derived from man-made fibers, such as polyester, nylon, and acrylic, which are produced through chemical processes involving petrochemicals.	Textiles, leather & furnishings	Not Available
CEDs000490		Personal care & cosmetics	Not Available
CEDs000492	Cell phones?Cell phones contain a variety of synthetic chemicals and materials, including plastics, metals, and glass, which can contribute to environmental contamination.	Electrical & Electronic Equipment	Not Available
CEDs000493	Capacitors?Capacitors are electronic components that store and release electrical energy, often using dielectric materials that can include synthetic chemicals.	Electrical & Electronic Equipment	Not Available
CEDs000653	Sewing?Sewing processes often involve the use of various synthetic chemicals, which can become sources of contamination in the environment.	Textiles, leather & furnishings	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

1 pathwayPathway Source: PathBank

Colchicine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Tubulin polymerization-promoting protein	Q27957	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.633 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 2 E-value 0.0778492
Click to view 3D structure	Tubulin alpha chain	P02550	Sus scrofa	Predicted (SEA)	Prediction Confidence Score 0.51 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 9 E-value 0.0778492
Click to view 3D structure	Tubulin beta chain	Q6B856	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.495 Applicability Domain 1.0 Statistical Significance 3.00e-05 Supporting Reference Compounds 12 E-value 0.233548
Click to view 3D structure	Serine/threonine-protein kinase pim-1	P11309	Humans	Predicted (SEA)	Prediction Confidence Score 0.382 Applicability Domain 1.0 Statistical Significance 0.0208 Supporting Reference Compounds 967 E-value 161.926
Click to view 3D structure	Nuclear receptor subfamily 0 group B member 1	P51843	Humans	Predicted (SEA)	Prediction Confidence Score 0.319 Applicability Domain 0.769 Statistical Significance 1.00e-05 Supporting Reference Compounds 17 E-value 0.0778492
Click to view 3D structure	Solute carrier family 22 member 3	O75751	Humans	Predicted (SEA)	Prediction Confidence Score 0.318 Applicability Domain 1.0 Statistical Significance 9.00e-05 Supporting Reference Compounds 17 E-value 0.700643
Click to view 3D structure	Tubulin beta chain	P07437	Humans	Predicted (SEA)	Prediction Confidence Score 0.299 Applicability Domain 1.0 Statistical Significance 2.00e-05 Supporting Reference Compounds 5 E-value 0.155698
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	Prediction Confidence Score 0.294 Applicability Domain 0.333 Statistical Significance 0.0554 Supporting Reference Compounds 565 E-value 431.518
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	Prediction Confidence Score 0.29 Applicability Domain 0.333 Statistical Significance 0.0907 Supporting Reference Compounds 953 E-value 705.937
Click to view 3D structure	D(1A) dopamine receptor	P21728	Humans	Predicted (SEA)	Prediction Confidence Score 0.287 Applicability Domain 0.317 Statistical Significance 0.0499 Supporting Reference Compounds 425 E-value 388.156
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	Prediction Confidence Score 0.287 Applicability Domain 0.317 Statistical Significance 0.1099 Supporting Reference Compounds 955 E-value 855.252
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	Prediction Confidence Score 0.285 Applicability Domain 0.29 Low confidence Statistical Significance 0.0969 Supporting Reference Compounds 823 E-value 754.125
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	Prediction Confidence Score 0.285 Applicability Domain 0.333 Statistical Significance 0.0793 Supporting Reference Compounds 686 E-value 617.734
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.276 Applicability Domain 0.29 Low confidence Statistical Significance 0.1535 Supporting Reference Compounds 1103 E-value 1195.06
Click to view 3D structure	Beta-2 adrenergic receptor	P07550	Humans	Predicted (SEA)	Prediction Confidence Score 0.269 Applicability Domain 0.333 Statistical Significance 0.0415 Supporting Reference Compounds 258 E-value 323.23
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	Prediction Confidence Score 0.269 Applicability Domain 0.333 Statistical Significance 0.097 Supporting Reference Compounds 536 E-value 755.215
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	Prediction Confidence Score 0.268 Applicability Domain 0.29 Low confidence Statistical Significance 0.1085 Supporting Reference Compounds 528 E-value 844.664
Click to view 3D structure	5-hydroxytryptamine receptor 1D	P28221	Humans	Predicted (SEA)	Prediction Confidence Score 0.268 Applicability Domain 0.333 Statistical Significance 0.0749 Supporting Reference Compounds 365 E-value 583.324
Click to view 3D structure	Cyclin-dependent kinase 2	P24941	Humans	Predicted (SEA)	Prediction Confidence Score 0.266 Applicability Domain 0.312 Statistical Significance 0.2441 Supporting Reference Compounds 1029 E-value 1900.14
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28222	Humans	Predicted (SEA)	Prediction Confidence Score 0.266 Applicability Domain 0.333 Statistical Significance 0.0771 Supporting Reference Compounds 337 E-value 600.14
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	Prediction Confidence Score 0.265 Applicability Domain 0.282 Low confidence Statistical Significance 0.1681 Supporting Reference Compounds 861 E-value 1308.96
Click to view 3D structure	Cyclin-dependent kinase 7	P50613	Humans	Predicted (SEA)	Prediction Confidence Score 0.265 Applicability Domain 0.312 Statistical Significance 0.1478 Supporting Reference Compounds 406 E-value 1150.77
Click to view 3D structure	Cyclin-dependent kinase 1	P06493	Humans	Predicted (SEA)	Prediction Confidence Score 0.265 Applicability Domain 0.312 Statistical Significance 0.2043 Supporting Reference Compounds 715 E-value 1590.23
Click to view 3D structure	Cyclin-dependent kinase 9	P50750	Humans	Predicted (SEA)	Prediction Confidence Score 0.263 Applicability Domain 0.312 Statistical Significance 0.1529 Supporting Reference Compounds 426 E-value 1190.63
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Predicted (SEA)	Prediction Confidence Score 0.261 Applicability Domain 0.267 Low confidence Statistical Significance 0.1475 Supporting Reference Compounds 524 E-value 1148.35
Click to view 3D structure	Tubulin beta-1 chain	Q9H4B7	Humans	Known	Not Available
Click to view 3D structure	Tubulin beta chain	P07437	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Known	Not Available
Click to view 3D structure	ATP-dependent translocase ABCB1	P08183	Humans	Known	Not Available
Click to view 3D structure	Nuclear receptor subfamily 0 group B member 1	P51843	Humans	Known	Not Available
Click to view 3D structure	Solute carrier family 22 member 3	O75751	Humans	Known	Not Available
Click to view 3D structure	Steroidogenic factor 1	Q13285	Humans	Known	Not Available
Click to view 3D structure	Protein c-Fos	P01100	Humans	Known	Not Available
Click to view 3D structure	Cellular tumor antigen p53	P04637	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01394

HMDB ID

HMDB0015466

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Christian Wehrey, “Colchicine derivatives, process for preparing them, products obtained therefrom and use thereof.” U.S. Patent US20040138182, issued July 15, 2004.

MSDS

Link

General References

Not Available

Colchicine (CED0001466)

Structure for CHEM002980: Colchicine

Structure