Colchiceine

Details

• Internal ID: 92b76074-404a-483a-beb0-03fe00adbfc9
• Taxonomy: Hydrocarbon derivatives > Tropones > Tropolones
• IUPAC Name: N-[(7S)-10-hydroxy-1,2,3-trimethoxy-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)O)OC)OC)OC
• SMILES (Isomeric): CC(=O)N[C@H]1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)O)OC)OC)OC
• InChI: InChI=1S/C21H23NO6/c1-11(23)22-15-7-5-12-9-18(26-2)20(27-3)21(28-4)19(12)13-6-8-16(24)17(25)10-14(13)15/h6,8-10,15H,5,7H2,1-4H3,(H,22,23)(H,24,25)/t15-/m0/s1
• InChI Key: PRGILOMAMBLWNG-HNNXBMFYSA-N
• Popularity: 143 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₃NO₆
• Molecular Weight: 385.40 g/mol
• Exact Mass: 385.15253745 g/mol
• Topological Polar Surface Area (TPSA): 94.10 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 2.57
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 477-27-0
• O10-Demethylcolchicine
• colchicein
• N-Acetyl trimethylcolchicinic acid
• NSC33411
• NSC 33411
• Coichiceine
• O-Demethylcolchicine
• Colchiceine (VAN)
• O(sup 10)-Demethylcolchicine
• UNII-HJ30158L57
• EINECS 207-512-5
• NSC-33411
• HJ30158L57
• NSC 123396
• NSC-123396
• BRN 2824078
• CHEMBL142588
• DTXSID60878565
• 4-14-00-00943 (Beilstein Handbook Reference)
• NSC123396
• Benzo(a)heptalen-10(5H)-one, 7-acetamido-6,7-dihydro-9-hydroxy-1,2,3-trimethoxy-
• Benzo(a)heptalen-9(5H)-one, 7-acetamido-6,7-dihydro-10-hydroxy-1,2,3-trimethoxy-
• N-[(7S)-10-hydroxy-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
• N-[(7S)-10-hydroxy-1,2,3-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• Acetamide, N-(5,6,7,9-tetrahydro-10-hydroxy-1,2,3-trimethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)-
• ACETAMIDE, N-((7S)-5,6,7,9-TETRAHYDRO-10-HYDROXY-1,2,3-TRIMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)-
• N-((7S)-5,6,7,9-TETRAHYDRO-10-HYDROXY-1,2,3-TRIMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)ACETAMIDE
• 7-Acetamido-10-hydroxy-1,2,3-trimethoxy-6,7-dihydrobenzo(a)heptalen-9(5H)-one
• WLN: L B677 MV&T&J CO1 DO1 EO1 JMV1 NQ
• MFCD00598980
• Benzo[a]heptalen-9(5H)-one,7-dihydro-10-hydroxy-1,2,3-trimethoxy-
• 7-Acetamido-10-hydroxy-1,3-trimethoxy-6,7-dihydrobenzo[a]heptalen-9(5H)-one
• Acetamide, N-(5,6,7,9-tetrahydro-10-hydroxy-1,2,3-trimethoxy-9-oxobenzo[a]heptalen-7-yl)-, (S)-
• Acetamide,6,7,9-tetrahydro-10-hydroxy-1,2,3-trimethoxy-9-oxobenzo[a]heptalen-7-yl)-, (S)-
• N-{(7s)-10-hydroxy-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl}acetamide
• Spectrum_000357
• SpecPlus_000827
• COLCHICEINE [MI]
• Spectrum2_000296
• Spectrum3_001161
• Spectrum4_000582
• Spectrum5_001013
• BSPBio_002741
• KBioGR_001044
• KBioSS_000837
• MLS002472977
• DivK1c_006923
• SCHEMBL177858
• SPECTRUM1800067
• SPBio_000232
• GTPL7525
• KBio1_001867
• KBio2_000837
• KBio2_003405
• KBio2_005973
• KBio3_002241
• CHEBI:183909
• DTXCID101016609
• HMS2205M17
• N-[(7S,12aRa)-10-Hydroxy-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide (Colchiceine)
• TNP00282
• BDBM50157477
• CCG-39854
• AKOS004110611
• MS-2274
• SDCCGMLS-0066903.P001
• N-((7S)-10-hydroxy-1,2,3-trimethoxy-9-oxo-5,6,7-trihydrobenzo[d]heptalen-7-yl) acetamide
• NCGC00017342-01
• NCGC00017342-02
• NCGC00017342-03
• NCGC00142518-01
• NCGC00178495-01
• NCI60_002925
• SMR001397084
• COLCHICINE IMPURITY F [EP IMPURITY]
• Q27089242
• 7-Acetamido-10-hydroxy-1,2,3-trimethoxy-6,7-dihydrobenzo(a)heptalen-9(5H)-one, (S)-
• N-[(7S)-10-hydroxy-1,2,3-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[d]heptalen-7-yl]acetamide
• (s)-n-(10-hydroxy-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide
• 2SJ
• N-((S)-10-Hydroxy-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-acetamide
• N-(10-Hydroxy-1,2,3-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide-, (S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9565	95.65%
Caco-2	+	0.5939	59.39%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Nucleus	0.5545	55.45%
OATP2B1 inhibitior	-	0.8782	87.82%
OATP1B1 inhibitior	+	0.9339	93.39%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9572	95.72%
BSEP inhibitior	+	0.8469	84.69%
P-glycoprotein inhibitior	-	0.8324	83.24%
P-glycoprotein substrate	+	0.9446	94.46%
CYP3A4 substrate	+	0.7282	72.82%
CYP2C9 substrate	-	0.8499	84.99%
CYP2D6 substrate	-	0.8224	82.24%
CYP3A4 inhibition	-	0.8740	87.40%
CYP2C9 inhibition	-	0.9265	92.65%
CYP2C19 inhibition	-	0.9458	94.58%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9396	93.96%
CYP2C8 inhibition	+	0.9510	95.10%
CYP inhibitory promiscuity	-	0.9241	92.41%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6712	67.12%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.8772	87.72%
Skin irritation	-	0.7813	78.13%
Skin corrosion	-	0.9443	94.43%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7183	71.83%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.6790	67.90%
skin sensitisation	-	0.9251	92.51%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5840	58.40%
Acute Oral Toxicity (c)	III	0.6069	60.69%
Estrogen receptor binding	+	0.7926	79.26%
Androgen receptor binding	+	0.8488	84.88%
Thyroid receptor binding	+	0.7771	77.71%
Glucocorticoid receptor binding	+	0.8447	84.47%
Aromatase binding	-	0.7024	70.24%
PPAR gamma	+	0.7416	74.16%
Honey bee toxicity	-	0.8892	88.92%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6449	64.49%
Fish aquatic toxicity	+	0.7505	75.05%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.07%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.24%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.03%	96.09%
CHEMBL217	P14416	Dopamine D2 receptor	94.34%	95.62%
CHEMBL2535	P11166	Glucose transporter	94.17%	98.75%
CHEMBL2581	P07339	Cathepsin D	93.44%	98.95%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	92.95%	91.79%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.64%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.97%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	89.00%	91.19%
CHEMBL2056	P21728	Dopamine D1 receptor	88.86%	91.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.65%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.01%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	86.72%	91.49%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.15%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.02%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.74%	93.03%
CHEMBL1075317	P61964	WD repeat-containing protein 5	84.39%	96.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.21%	95.89%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.21%	89.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.17%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.05%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.23%	99.15%
CHEMBL4208	P20618	Proteasome component C5	80.99%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.67%	97.14%
CHEMBL259	P32245	Melanocortin receptor 4	80.49%	95.38%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.44%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.16%	94.33%

Plants that contains it

• Colchicum autumnale
• Colchicum laetum
• Colchicum ritchiei

Cross-Links

• PubChem: 234105
• LOTUS: LTS0219446
• wikiData: Q27089242