O(sup 2)-Demethylcolchicine

Details

• Internal ID: 0b474769-87b8-425e-b59f-13c88d3534a1
• Taxonomy: Hydrocarbon derivatives > Tropones
• IUPAC Name: N-(2-hydroxy-1,3,10-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)OC)OC)O)OC
• SMILES (Isomeric): CC(=O)NC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)O)OC
• InChI: InChI=1S/C21H23NO6/c1-11(23)22-15-7-5-12-9-18(27-3)20(25)21(28-4)19(12)13-6-8-17(26-2)16(24)10-14(13)15/h6,8-10,15,25H,5,7H2,1-4H3,(H,22,23)
• InChI Key: DPOVAJCRYIUTBD-UHFFFAOYSA-N
• Popularity: 1 reference 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: 0.50
• Atomic LogP (AlogP): 2.57
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• Acetamide, N-(5,6,7,9-tetrahydro-2-hydroxy-1,3,10-trimethoxy-9-oxobenzo[a]heptalen-7-yl)-
• O(sup 2)-Demethylcolchicine
• Isocolchiceine
• COLCHICINE, O(sup 2)-DEMETHYL-
• CHEMBL325328
• DPOVAJCRYIUTBD-UHFFFAOYSA-N
• Acetamide, N-(5,6,7,9-tetrahydro-2-hydroxy-1,3,10-trimethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)-
• FT-0665699
• N-(2-Hydroxy-1,3,10-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9565	95.65%
Caco-2	+	0.6634	66.34%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Nucleus	0.5545	55.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9106	91.06%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9572	95.72%
BSEP inhibitior	+	0.9018	90.18%
P-glycoprotein inhibitior	-	0.8140	81.40%
P-glycoprotein substrate	+	0.9596	95.96%
CYP3A4 substrate	+	0.7476	74.76%
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	+	0.9639	96.39%
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	-	0.8929	89.29%
Skin irritation	-	0.7813	78.13%
Skin corrosion	-	0.9443	94.43%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6449	64.49%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.7522	75.22%
skin sensitisation	-	0.9251	92.51%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.4575	45.75%
Acute Oral Toxicity (c)	III	0.6069	60.69%
Estrogen receptor binding	+	0.8081	80.81%
Androgen receptor binding	+	0.8203	82.03%
Thyroid receptor binding	+	0.7933	79.33%
Glucocorticoid receptor binding	+	0.8079	80.79%
Aromatase binding	-	0.6397	63.97%
PPAR gamma	+	0.7352	73.52%
Honey bee toxicity	-	0.8924	89.24%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
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	98.45%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.76%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.75%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.16%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.67%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.64%	90.71%
CHEMBL217	P14416	Dopamine D2 receptor	90.45%	95.62%
CHEMBL2056	P21728	Dopamine D1 receptor	89.78%	91.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.43%	99.17%
CHEMBL2535	P11166	Glucose transporter	89.30%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	88.00%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.83%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.02%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.15%	95.89%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.73%	93.03%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.84%	92.62%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.68%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.36%	95.89%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.30%	96.38%
CHEMBL4208	P20618	Proteasome component C5	83.44%	90.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	82.29%	91.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.25%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.76%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.10%	99.23%

Plants that contains it

• Colchicum autumnale
• Colchicum bivonae
• Colchicum doerfleri
• Colchicum soboliferum
• Colchicum trigynum
• Sandersonia aurantiaca

Cross-Links

• PubChem: 541033
• LOTUS: LTS0202596
• wikiData: Q104986638