(R)-colchicine

Details

• Internal ID: 85867c58-0501-484e-a9c9-0689dc642867
• Taxonomy: Hydrocarbon derivatives > Tropones
• IUPAC Name: N-[(7R)-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-/m1/s1
• InChI Key: IAKHMKGGTNLKSZ-MRXNPFEDSA-N
• Popularity: 11 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
• Atomic LogP (AlogP): 2.87
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 75520-89-7
• COLCHICINE, (+)-
• N-[(7R)-1,2,3,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• CHEBI:51074
• N-[(7R)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
• (+)-Colchicine
• CAS-64-86-8
• COLCHICINE natural
• Lopac-C-9754
• NCIMech_000874
• Acetamide, N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo(a)heptalen-7-yl)-, (R)-
• Oprea1_777295
• CHEMBL330320
• SCHEMBL15521905
• DTXSID60226466
• TNP00005
• CCG-35801
• CCG-36032
• NCGC00015286-01
• NCGC00016293-01
• NCGC00017162-01
• NCGC00017162-02
• NCGC00142480-01
• Q27122333
• (R)-N-(5,6,7,9-tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9855	98.55%
Caco-2	+	0.7766	77.66%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Nucleus	0.4640	46.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9308	93.08%
OATP1B3 inhibitior	+	0.9589	95.89%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9322	93.22%
BSEP inhibitior	+	0.9192	91.92%
P-glycoprotein inhibitior	-	0.8485	84.85%
P-glycoprotein substrate	+	0.9713	97.13%
CYP3A4 substrate	+	0.7604	76.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8323	83.23%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.9817	98.17%
CYP inhibitory promiscuity	-	0.7959	79.59%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6626	66.26%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9171	91.71%
Skin irritation	-	0.7907	79.07%
Skin corrosion	-	0.9478	94.78%
Ames mutagenesis	-	0.9700	97.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4207	42.07%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	-	0.8198	81.98%
skin sensitisation	-	0.9341	93.41%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.6282	62.82%
Acute Oral Toxicity (c)	III	0.6116	61.16%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.8461	84.61%
Glucocorticoid receptor binding	+	0.8433	84.33%
Aromatase binding	-	0.6515	65.15%
PPAR gamma	+	0.6818	68.18%
Honey bee toxicity	-	0.8973	89.73%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.7913	79.13%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293278	O75496	Geminin	39.8 nM	Potency	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	199.5 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	79.4 nM; 8.9 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL1293256	P40225	Thrombopoietin	501.2 nM	Potency	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	125.9 nM	Potency	via Super-PRED

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

• Colchicum autumnale
• Colchicum doerfleri
• Colchicum robustum
• Colchicum trigynum

Cross-Links

• PubChem: 53278
• LOTUS: LTS0257848
• wikiData: Q27122333