3-Desmethylcolchicine

Details

• Internal ID: cd4851cb-eb99-4929-8660-601ba0acca74
• Taxonomy: Hydrocarbon derivatives > Tropones
• IUPAC Name: N-[(7S)-3-hydroxy-1,2,10-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)OC)O
• SMILES (Isomeric): CC(=O)N[C@H]1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)O
• InChI: InChI=1S/C21H23NO6/c1-11(23)22-15-7-5-12-9-17(25)20(27-3)21(28-4)19(12)13-6-8-18(26-2)16(24)10-14(13)15/h6,8-10,15,25H,5,7H2,1-4H3,(H,22,23)/t15-/m0/s1
• InChI Key: JRRUSQGIRBEMRN-HNNXBMFYSA-N
• Popularity: 5 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: 0.70
• Atomic LogP (AlogP): 2.57
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 3-Demethylcolchicine
• 7336-33-6
• 3-Demethyl Colchicine
• O3-Demethylcolchicine
• (-)-3-demethylcolchicine
• 3-O-Demethylcolchicine
• Desmethylcolchicine
• Colchicine, O(3)-demethyl-
• O3-Demethyl colchicine
• Colchicine, 2-demethyl-
• Colchiciine, 3-desmethyl-
• Colchicine, O(sup 3)-demethyl-
• N-[(7S)-3-hydroxy-1,2,10-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• NSC 50164
• NSC172946
• UNII-C939KS8QEL
• 3-DESMETHYLCOLCHICIN
• NSC 172946
• C939KS8QEL
• CHEMBL1081
• COLCHICINE, 3-O-DEMETHYL-
• NSC-172946
• Benzoheptalen-9(5H)-one, 7-acetamido-6,7-dihydro-, L-
• Acetamide, N-(5,6,7,9-tetrahydro-3-hydroxy-1,2,10-trimethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)
• Acetamide, N-(5,6,7,9-tetrahydro-3-hydroxy-1,2,10-trimethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)-
• N-(5,6,7,9-Tetrahydro-3-hydroxy-1,2,10-trimethoxy-9-oxobenzo(a)heptalen-7-yl)acetamide (S)-
• N-[(7S,12aRa)-3-Hydroxy-1,2,10-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide (3-O-Demethylcolchicine)
• MLS002703022
• COLCHICINE,3-DESMETHYL
• 3-Demethyl-(-)-colchicine
• Acetamide, N-(5,6,7,9-tetrahydro-3-hydroxy-1,2,10-trimethoxy-9-oxobenzo[a]heptalen-7-yl)-, (S)-
• cid_494161
• 3-O-DEMETHYL COLCHICINE
• SCHEMBL12246871
• COLCHICINE, O3-DEMETHYL-
• DTXSID30223604
• JRRUSQGIRBEMRN-HNNXBMFYSA-N
• BDBM50014866
• AKOS040763648
• HY-W021267
• AS-83238
• LS-54685
• NCI60_001400
• PD011312
• Q27275337
• N-(3-Hydroxy-1,2,10-trimethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-acetamide
• 160338-75-0
• ACETAMIDE, N-((7S)-5,6,7,9-TETRAHYDRO-3-HYDROXY-1,2,10-TRIMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)-
• Acetamide,6,7,9-tetrahydro-3-hydroxy-1,2,10-trimethoxy-9-oxobenzo[a]heptalen-7-yl)-, (S)-
• N-(5,6,7,9-Tetrahydro-3-hydroxy-1,2,10-trimethoxy-9-oxobenzo[a]heptalen-7-ylacetamide (S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9149	91.49%
Caco-2	+	0.6192	61.92%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Nucleus	0.5491	54.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9200	92.00%
OATP1B3 inhibitior	+	0.9473	94.73%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9393	93.93%
BSEP inhibitior	+	0.8343	83.43%
P-glycoprotein inhibitior	-	0.8114	81.14%
P-glycoprotein substrate	+	0.9433	94.33%
CYP3A4 substrate	+	0.7350	73.50%
CYP2C9 substrate	-	0.8499	84.99%
CYP2D6 substrate	-	0.8224	82.24%
CYP3A4 inhibition	-	0.8963	89.63%
CYP2C9 inhibition	-	0.8967	89.67%
CYP2C19 inhibition	-	0.9207	92.07%
CYP2D6 inhibition	-	0.9140	91.40%
CYP1A2 inhibition	-	0.9072	90.72%
CYP2C8 inhibition	+	0.9561	95.61%
CYP inhibitory promiscuity	-	0.8828	88.28%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6683	66.83%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.8942	89.42%
Skin irritation	-	0.7701	77.01%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4726	47.26%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	-	0.6698	66.98%
skin sensitisation	-	0.9257	92.57%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.5749	57.49%
Acute Oral Toxicity (c)	III	0.5862	58.62%
Estrogen receptor binding	+	0.7850	78.50%
Androgen receptor binding	+	0.8292	82.92%
Thyroid receptor binding	+	0.7227	72.27%
Glucocorticoid receptor binding	+	0.8081	80.81%
Aromatase binding	-	0.5093	50.93%
PPAR gamma	+	0.7513	75.13%
Honey bee toxicity	-	0.8945	89.45%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.7770	77.70%

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	98.39%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.09%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.85%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.18%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	94.86%	91.49%
CHEMBL217	P14416	Dopamine D2 receptor	94.24%	95.62%
CHEMBL2535	P11166	Glucose transporter	92.81%	98.75%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	92.19%	91.79%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.81%	90.71%
CHEMBL2056	P21728	Dopamine D1 receptor	89.26%	91.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.19%	99.17%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.81%	93.03%
CHEMBL340	P08684	Cytochrome P450 3A4	86.98%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.30%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.78%	89.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	85.70%	96.38%
CHEMBL4208	P20618	Proteasome component C5	84.94%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.77%	95.89%
CHEMBL1075317	P61964	WD repeat-containing protein 5	84.35%	96.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.07%	95.89%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.96%	89.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.95%	99.23%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.00%	96.21%
CHEMBL4040	P28482	MAP kinase ERK2	81.31%	83.82%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.30%	92.62%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.48%	94.33%

Plants that contains it

• Colchicum arenarium
• Colchicum autumnale
• Colchicum bivonae
• Colchicum kesselringii
• Colchicum ritchiei
• Colchicum robustum
• Colchicum soboliferum
• Colchicum speciosum
• Colchicum szovitsii subsp. brachyphyllum
• Gloriosa superba
• Sandersonia aurantiaca
• Wurmbea dioica

Cross-Links

• PubChem: 299664
• NPASS: NPC66678
• ChEMBL: CHEMBL1081
• LOTUS: LTS0271726
• wikiData: Q27275337