Colchicine

Details

• Internal ID: 92d910e5-2f45-426c-8901-3b8499bcf9ab
• Taxonomy: Hydrocarbon derivatives > Tropones
• IUPAC Name: N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• SMILES (Canonical): CC(=O)NC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
• SMILES (Isomeric): CC(=O)N[C@H]1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
• InChI: 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)/t16-/m0/s1
• InChI Key: IAKHMKGGTNLKSZ-INIZCTEOSA-N
• Popularity: 37,308 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₅NO₆
• Molecular Weight: 399.40 g/mol
• Exact Mass: 399.16818752 g/mol
• Topological Polar Surface Area (TPSA): 83.10 Ų
• XlogP: 1.00

Synonyms

• 64-86-8
• Colchisol
• Colchineos
• Colcin
• Colchicinum
• Colchicin
• Colchicina
• Condylon
• Colsaloid
• Colcrys
• 7alphaH-Colchicine
• Goutnil
• Kolkicin
• (S)-colchicine
• (-)-colchicine
• Colchysat
• Mitigare
• spindle poison
• 7-alpha-H-Colchicine
• Colchicine [JAN]
• Colchicin [German]
• Colchicina [Italian]
• NSC 757
• CCRIS 691
• Colchcine
• Colstat
• NSC757
• N-Acetyl trimethylcolchicinic acid methylether
• HSDB 3044
• NSC-757
• N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• UNII-SML2Y3J35T
• (S)-colchicina
• (S)-colchicin
• Colchicine (TN)
• EINECS 200-598-5
• SML2Y3J35T
• Benzo(a)heptalen-9(5H)-one
• GLOPERBA
• DTXSID5024845
• 7.alpha.H-Colchicine
• CHEBI:27882
• AI3-31149
• Colchicine [USP:JAN]
• (S)-N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide
• N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
• MFCD00078484
• CHEMBL107
• DTXCID204845
• XD25
• MPC-004
• EC 200-598-5
• MITIGARE COMPONENT COLCHICINE
• PROBEN-C COMPONENT COLCHICINE
• Benzo(a)heptalen-9(5H)-one, 7-acetamido-6,7-dihydro-1,2,3,10-tetramethoxy-
• Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)-
• COLBENEMID COMPONENT COLCHICINE
• N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)acetamide
• COLCHICINE COMPONENT OF MITIGARE
• COLCHICINE COMPONENT OF PROBEN-C
• NCGC00025125-07
• COLCHICINE COMPONENT OF COLBENEMID
• COL-PROBENECID COMPONENT COLCHICINE
• Colchicine, (R)-Isomer
• COLCHICINE COMPONENT OF COL-PROBENECID
• C 9754
• COLCHICINE (MART.)
• COLCHICINE [MART.]
• COLCHICINE (USP-RS)
• COLCHICINE [USP-RS]
• N-[(7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]acetamide
• COLCHICINE (EP IMPURITY)
• COLCHICINE [EP IMPURITY]
• COLCHICINE (EP MONOGRAPH)
• COLCHICINE [EP MONOGRAPH]
• COLCHICINE (USP MONOGRAPH)
• COLCHICINE [USP MONOGRAPH]
• Acetamide, N-((7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-
• Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(alpha)heptalen-7-yl)-
• Acetamide, N-[(7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]-
• N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[.alpha.]heptalen-7-yl)-acetamide
• N-[(7s)-1,2,3,10-Tetramethoxy-9-Oxo-6,7-Dihydro-5h-Benzo[d]heptalen-7-Yl]ethanamide
• (S)-N-(5,6,7,9-TETRAHYDRO-1,2,3,10-TETRAMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)ACETAMIDE
• 30512-31-3
• ACETAMIDE, N-(5,6,7,9-TETRAHYDRO-1,2,3,10-TETRAMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)-,(S)-
• LOC
• SMR000058323
• 7alpha-H-Colchicine
• BENZO(A)HEPTALENE, ACETAMIDE DERIV.
• Colchicine, Colchicum autumnale
• (S)-Colchicine >95%
• SR-01000075794
• SR-01000597576
• Colchicine, (+-)-Isomer
• binds to tubulin
• 4lzr
• Acetamide,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(.alpha.)heptalen-7-yl)-
• Acetamide,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[.alpha.]heptalen-7-yl)-
• N-((7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo(a)heptalen-7-yl)acetamide
• N-((7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)- acetamide
• CAS-64-86-8
• Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)-, (S)-
• Prestwick_695
• COLCHICENOS
• Spectrum_000842
• Tocris-1364
• 4o2b
• COLCHICINE [MI]
• Prestwick0_000363
• Prestwick1_000363
• Prestwick2_000363
• Prestwick3_000363
• Spectrum2_000075
• Spectrum3_000362
• Spectrum4_000298
• Spectrum5_000787
• COLCHCINE [VANDF]
• COLCHICINE [HSDB]
• COLCHICINUM [HPUS]
• Colchicine (JP15/USP)
• Colchicine (JP17/USP)
• D09DHY
• UPCMLD-DP065
• SCHEMBL8469
• COLCHICINE [WHO-DD]
• COLCHICINE [WHO-IP]
• Lopac0_000310
• BSPBio_000485
• BSPBio_002083
• inhibits microtubular assembly
• KBioGR_000856
• KBioSS_001322
• Colchicine (contains 5% Ethyl Acetate at maximum)
• MLS001055448
• MLS001304089
• MLS002153786
• DivK1c_000753
• SPECTRUM1500205
• SPBio_000289
• SPBio_002406
• COLCHICEINE METHYL ETHER
• BPBio1_000535
• GTPL2367
• MEGxp0_001879
• COLCHICINE [ORANGE BOOK]
• UPCMLD-DP065:001
• ACon1_000353
• HMS502F15
• KBio1_000753
• KBio2_001322
• KBio2_003890
• KBio2_006458
• KBio3_001303
• NINDS_000753
• HMS1569I07
• HMS1920A08
• HMS2091G16
• HMS2096I07
• HMS2231C05
• HMS3260N22
• HMS3713I07
• Pharmakon1600-01500205
• COLCHICINUM [WHO-IP LATIN]
• Acetamida, n-[(7s)-5,6,7,9-tetrahidro-1,2,3,10-tetrametoxi-9-oxobenzo [a] heptalen-7-il]-
• Acetamide, N-(5,6,7,9-tetrahydro-1,2, 3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)-, (S)-
• Colchicine, >=96.0% (HPLC)
• Tox21_110947
• Tox21_201547
• Tox21_300582
• Tox21_500310
• BDBM50014846
• CCG-39910
• LS-279
• NSC756702
• NSC813203
• s2284
• AKOS001582887
• Colchicine, >=95% (HPLC), powder
• Tox21_110947_1
• CS-1141
• DB08117
• LP00310
• NSC-756702
• NSC-813203
• SDCCGMLS-0066633.P001
• SDCCGSBI-0050298.P006
• IDI1_000753
• NCGC00025125-01
• NCGC00025125-02
• NCGC00025125-03
• NCGC00025125-04
• NCGC00025125-05
• NCGC00025125-06
• NCGC00025125-08
• NCGC00025125-09
• NCGC00025125-10
• NCGC00025125-11
• NCGC00025125-12
• NCGC00025125-13
• NCGC00025125-14
• NCGC00025125-15
• NCGC00025125-18
• NCGC00025125-20
• NCGC00025125-33
• NCGC00169157-01
• NCGC00169157-02
• NCGC00169157-03
• NCGC00254359-01
• NCGC00259096-01
• NCGC00260995-01
• AS-13686
• HY-16569
• NCI60_041659
• SBI-0050298.P004
• EU-0100310
• FT-0603187
• MLS001055448-02
• (-)-N-
• C-7100
• C07592
• D00570
• M01514
• binds to tubulin; inhibits microtubular assembly
• SR-01000075794-1
• SR-01000075794-3
• SR-01000075794-6
• SR-01000075794-7
• SR-01000597576-1
• SR-01000597576-3
• BRD-K00259736-001-06-5
• BRD-K00259736-001-10-7
• N-ACETYLTRIMETHYLCOLCHICINIC ACID METHYL ETHER
• WLN: L B677 MV&T&J CO1 DO1 EO1 JMV1 NO1
• N-ACETYL TRIMETHYLCOLCHICINIC ACID, METHYL ETHER
• Benzo[a]heptalen-9(5H)-one,7-dihydro-1,2,3,10-tetramethoxy-
• Colchicine, (European Pharmacopoeia (EP) Reference Standard)
• Colchicine, United States Pharmacopeia (USP) Reference Standard
• Colchicine, BioReagent, plant cell culture tested, >=95% (HPLC)
• N-((7S)-5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo
• 7-Acetamido-6,7-dihydro-1,2,3,10-tetramethoxy-benzo(a)heptalen-9(5H)-one
• Colchicine, Pharmaceutical Secondary Standard; Certified Reference Material
• 7-ACETAMIDO-6,7-DIHYDRO-1,2,3,10-TETRAMETHOXYBENZO(A)HEPTALEN-9(5H)-ONE
• Colchicine for system suitability, European Pharmacopoeia (EP) Reference Standard
• N-((7S)-(1,2,3,10-Tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo(a)heptalen-7-yl))acetamide
• N-((7S)-5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-acetamide
• N-(5,6,7,9-TETRAHYDRO-1,2,3,10-TETRAMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)-ACETAMIDE
• N-[(7S)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl]acetamide
• (1e)-N-[(7s)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl] ethanimidic acid
• ACETAMIDE, N-(5,6,7,9-TETRAHYDRO-1,2,3,10-TETRAMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)
• N-((7S)-5,6,7,9-TETRAHYDRO-1,2,3,10-TETRAMETHOXY-9-OXOBENZ(A)HEPTALEN-7-YL)-ACETAMIDE
• N-(5,6,7,9-TETRAHYDRO-1,2,3,10-TETRAMETHOXY-9-OXOBENZO(ALPHA)HEPTALEN-7-YL)-ACETAMIDE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4801	P29466	Caspase-1	39810.7 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	1584.9 nM	Potency	via CMAUP
CHEMBL5747	Q92793	CREB-binding protein	5011.9 nM; 5011.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	25118.86 nM	AC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	12589.25 nM	AC50	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	3162.28 nM	AC50	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	794.3 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	2511.9 nM; 2511.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293278	O75496	Geminin	39.8 nM; 39.8 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	199.5 nM	Potency	via Super-PRED
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	2511.9 nM	Potency	via CMAUP
CHEMBL2362980	Q06710	Paired box protein Pax-8	< 260 nM	AC50	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	79.4 nM; 70.8 nM; 8.9 nM; 125.9 nM; 8.9 nM	Potency; Potency; Potency; Potency; Potency	via Super-PRED; via CMAUP; via Super-PRED; via CMAUP; via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	1995.3 nM; 580478.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2073673	O75751	Solute carrier family 22 member 3	120 nM	Ki	PMID: 10196521
CHEMBL1293256	P40225	Thrombopoietin	501.2 nM; 501.2 nM; 501.2 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	125.9 nM; 1995.3 nM; 15848.9 nM; 15848.9 nM; 1995.3 nM	Potency; Potency; Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP; via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.27%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.17%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.67%	98.95%
CHEMBL2535	P11166	Glucose transporter	91.74%	98.75%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.37%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.91%	99.17%
CHEMBL217	P14416	Dopamine D2 receptor	88.81%	95.62%
CHEMBL2056	P21728	Dopamine D1 receptor	87.98%	91.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	87.91%	93.03%
CHEMBL1075317	P61964	WD repeat-containing protein 5	87.34%	96.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.97%	95.89%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	86.16%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	85.47%	91.19%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	85.09%	96.38%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.63%	89.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.19%	95.89%
CHEMBL4208	P20618	Proteasome component C5	83.50%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.75%	92.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.48%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.35%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.01%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.84%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	80.67%	91.49%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.39%	97.14%

Plants that contains it

• Artemisia lagocephala
• Colchicum arenarium
• Colchicum autumnale
• Colchicum bivonae
• Colchicum crocifolium
• Colchicum kesselringii
• Colchicum laetum
• Colchicum luteum
• Colchicum raddeanum
• Colchicum ritchiei
• Colchicum robustum
• Colchicum soboliferum
• Colchicum speciosum
• Colchicum szovitsii
• Colchicum szovitsii subsp. brachyphyllum
• Gagea lutea
• Ginkgo biloba
• Gloriosa superba
• Sandersonia aurantiaca
• Schelhammera multiflora
• Tanacetum parthenium
• Veratrum nigrum
• Wurmbea dioica

Cross-Links

• PubChem: 6167
• NPASS: NPC226941
• ChEMBL: CHEMBL107
• LOTUS: LTS0016789
• wikiData: Q326224