ChemFOnt: Showing chemical card for Colchicine (CFc000009736)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:58 UTC

Chemfont ID

CFc000009736

Molecule Identification

Common Name

Colchicine

Definition

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 SDF PDB SMILES InChI

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 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015466)
Membrane (HMDB: HMDB0015466)

Source

Exogenous

Exogenous (HMDB: HMDB0015466)

Process

Not Available

Role

Biological role

Mutagen (HMDB: HMDB0015466)

Physical Properties

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