Thiocolchicoside

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Thiocolchicoside are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Thiocolchicoside?

The molecule Thiocolchicoside presents a molecular formula of C27H33NO10S and its IUPAC name is N-[(7S)-1,2-dimethoxy-10-methylsulfanyl-9-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide.

Thiocolchicoside (TCC) is a molecule with the chemical structure C22H32OS2. It is a derivative of the plant alkaloid colchicine, and is used as a muscle relaxant..

TCC was first isolated from the bulbs of the Colchicum autumnale plant in the early 1900s. The molecule has since been synthesized in the laboratory. TCC is structurally similar to colchicine, and shares many of its pharmacological properties..

TCC binds to tubulin, the protein that makes up the microtubules of cells. This binding prevents the microtubules from assembling, and disrupts the cell's internal transport system. As a result, TCC inhibits cell division..

TCC is used as a treatment for muscle spasms and pain. It is typically given as an injection, but can also be taken orally. TCC is generally well-tolerated, but can cause side effects such as gastrointestinal upset, dizziness, and drowsiness..

TCC is a potentially useful drug for the treatment of a variety of conditions, but its use is limited by its side effects. Further research is needed to determine the full therapeutic potential of this molecule..

3D structure

Cartesian coordinates

Geometry of Thiocolchicoside in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Thiocolchicoside LEQAKWQJCITZNK-AXHKHJLKSA-N chemical compound 2D structure molecule svg
Thiocolchicoside

 

Molecule descriptors

 
IUPAC nameN-[(7S)-1,2-dimethoxy-10-methylsulfanyl-9-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
InChI codeInChI=1S/C27H33NO10S/c1-12(30)28-16-7-5-13-9-18(37-27-24(34)23(33)22(32)19(11-29)38-27)25(35-2)26(36-3)21(13)14-6-8-20(39-4)17(31)10-15(14)16/h6,8-10,16,19,22-24,27,29,32-34H,5,7,11H2,1-4H3,(H,28,30)/t16-,19+,22+,23-,24+,27+/m0/s1
InChI KeyLEQAKWQJCITZNK-AXHKHJLKSA-N
SMILESCOc1c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc2c(c1OC)-c1ccc(SC)c(=O)cc1[C@@H](NC(C)=O)CC2

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (s)-(methylthio)-9-oxobenzo(a)heptalen-7-yl)
  • 10-Thiocolchicoside
  • 10-thio-Colchicoside
  • 2-10-Di(demethoxy)-2-glucosyloxy-10-methylthiocolchicine
  • 2-Demethoxy-2-glucosidoxythiocolchicine
  • 602-41-5
  • 602T415
  • A914515
  • AC-34475
  • AS-14082
  • Acetamide, N-(3-(beta-D-glucopyranosyloxy)-5,6,7,9-tetrahydro-1,2-dimethoxy-10-(methylthio)-9-oxobenzo(a)heptalen-7-yl)-, (S)-
  • BDBM233193
  • BRN 0072205
  • BRN0072205
  • CCG-220539
  • CS-0008802
  • Colchicoside, 10-thio-
  • Coltramyl
  • Coltrax
  • D07276
  • DB11582
  • DSSTox_CID_25330
  • DSSTox_GSID_45330
  • DSSTox_RID_80807
  • HMS3713L19
  • HMS3886E11
  • HY-N0301
  • MFCD07995056
  • Miorel
  • Musco-ril
  • N-[(7S)-1,2-dimethoxy-10-(methylthio)-9-oxo-3-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
  • N-[(7S)-1,2-dimethoxy-10-methylsulfanyl-9-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
  • NCGC00016519-01
  • NSC 147755
  • NSC-147755
  • NSC147755
  • Q-201823
  • R. 271
  • T1X8S697GT
  • Thiocolchicine 2-glucoside analog
  • Thiocolchicoside
  • Thiocolchicoside (INN)
  • Thiocolchicosidum
  • Tiocolchicoside
  • Tiocolchicosido
  • s5049

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4245665
  • CAS-602-41-5
  • UNII-T1X8S697GT
  • AKOS016010119
  • BRD-K26619122-001-01-3
  • DTXSID5045330
  • CHEMBL213907
  • CHEBI:94557
  • Tox21_110470
  • EINECS 210-017-7
  • SCHEMBL240410

Physico-Chemical properties

IUPAC nameN-[(7S)-1,2-dimethoxy-10-methylsulfanyl-9-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
Molecular formulaC27H33NO10S
Molecular weight563.617
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity142.24
LogP1.1
Topological polar surface area189.3

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.