Cornigerine

Details

• Internal ID: 86b0aa9a-869d-45ba-b658-9b12412a8b13
• Taxonomy: Organoheterocyclic compounds > Benzodioxoles
• IUPAC Name: N-(5,19-dimethoxy-6-oxo-15,17-dioxatetracyclo[10.7.0.02,8.014,18]nonadeca-1(19),2,4,7,12,14(18)-hexaen-9-yl)acetamide
• SMILES (Canonical): CC(=O)NC1CCC2=CC3=C(C(=C2C4=CC=C(C(=O)C=C14)OC)OC)OCO3
• SMILES (Isomeric): CC(=O)NC1CCC2=CC3=C(C(=C2C4=CC=C(C(=O)C=C14)OC)OC)OCO3
• InChI: InChI=1S/C21H21NO6/c1-11(23)22-15-6-4-12-8-18-20(28-10-27-18)21(26-3)19(12)13-5-7-17(25-2)16(24)9-14(13)15/h5,7-9,15H,4,6,10H2,1-3H3,(H,22,23)
• InChI Key: DCYAJVOKJAFSES-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₁NO₆
• Molecular Weight: 383.40 g/mol
• Exact Mass: 383.13688739 g/mol
• Topological Polar Surface Area (TPSA): 83.10 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 6877-25-4
• NSC 358825
• Acetamide, N-(4,6,7,8-tetrahydro-3,13-dimethoxy-4-oxoheptaleno(1,2-f)(1,3)benzodioxol-6-yl)-, (S)-
• N-(5,19-dimethoxy-6-oxo-15,17-dioxatetracyclo[10.7.0.02,8.014,18]nonadeca-1(19),2,4,7,12,14(18)-hexaen-9-yl)acetamide
• NSC358825
• SCHEMBL8102208
• DTXSID70875308
• DCYAJVOKJAFSES-UHFFFAOYSA-N
• NSC-358825
• 2,3-(Methylenedioxy)-2,3-didemethoxycolchicine
• Colchicine, 2,3-desdimethyl-2,3-methylenedioxy-
• Acetamide,6,7,8-tetrahydro-3,13-dimethoxy-4-oxoheptaleno[1,2-f][1,3]benzodioxol-6-yl)-, (S)-
• Acetamide,6,7,8-tetrahydro-3,13-dimethyoxy-4-oxoheptaleno[1,2-f][1,3]benzodioxol-6-yl)-, (S)-
• N-(3,13-Dimethoxy-4-oxo-4,6,7,8-tetrahydroheptaleno[1,2-f][1,3]benzodioxol-6-yl)acetamide #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9737	97.37%
Caco-2	+	0.6183	61.83%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Nucleus	0.4915	49.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9186	91.86%
OATP1B3 inhibitior	+	0.9398	93.98%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9380	93.80%
P-glycoprotein inhibitior	-	0.6013	60.13%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.7180	71.80%
CYP2C9 substrate	-	0.8292	82.92%
CYP2D6 substrate	-	0.8516	85.16%
CYP3A4 inhibition	+	0.5974	59.74%
CYP2C9 inhibition	-	0.7179	71.79%
CYP2C19 inhibition	-	0.7570	75.70%
CYP2D6 inhibition	-	0.9199	91.99%
CYP1A2 inhibition	-	0.6773	67.73%
CYP2C8 inhibition	+	0.9100	91.00%
CYP inhibitory promiscuity	-	0.5511	55.11%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6283	62.83%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9496	94.96%
Skin irritation	-	0.7808	78.08%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3919	39.19%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.7198	71.98%
skin sensitisation	-	0.8647	86.47%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.6884	68.84%
Acute Oral Toxicity (c)	III	0.5771	57.71%
Estrogen receptor binding	+	0.9031	90.31%
Androgen receptor binding	+	0.8403	84.03%
Thyroid receptor binding	+	0.7553	75.53%
Glucocorticoid receptor binding	+	0.8425	84.25%
Aromatase binding	-	0.5577	55.77%
PPAR gamma	+	0.7182	71.82%
Honey bee toxicity	-	0.8287	82.87%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.7981	79.81%

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	98.11%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	96.71%	83.82%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.66%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.33%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.31%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.27%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.84%	92.62%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	91.92%	82.67%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	91.66%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.10%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.85%	89.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	88.17%	89.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.08%	90.71%
CHEMBL2535	P11166	Glucose transporter	87.44%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	87.00%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.99%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.31%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.22%	86.33%
CHEMBL1075317	P61964	WD repeat-containing protein 5	83.58%	96.33%
CHEMBL4208	P20618	Proteasome component C5	83.21%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.11%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.95%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.89%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.50%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.40%	100.00%
CHEMBL2056	P21728	Dopamine D1 receptor	82.39%	91.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.82%	95.78%
CHEMBL261	P00915	Carbonic anhydrase I	81.06%	96.76%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.82%	94.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.00%	96.38%

Plants that contains it

• Camptorrhiza strumosa
• Colchicum kurdicum
• Colchicum laetum
• Colchicum raddeanum
• Colchicum schimperi
• Colchicum speciosum
• Colchicum szovitsii subsp. brachyphyllum
• Colchicum tunicatum
• Corydalis sewerzowi
• Gloriosa superba
• Wurmbea dioica

Cross-Links

• PubChem: 100188
• NPASS: NPC120215
• LOTUS: LTS0019687
• wikiData: Q82856674