1,2,3,10-tetramethoxy-7-(methylamino)-6,7-dihydro-5H-benzo[a]heptalen-9-one

Details

• Internal ID: e28397d7-78cf-4cc3-9237-e27b3e7302f6
• Taxonomy: Hydrocarbon derivatives > Tropones
• IUPAC Name: 1,2,3,10-tetramethoxy-7-(methylamino)-6,7-dihydro-5H-benzo[a]heptalen-9-one
• SMILES (Canonical): CNC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
• SMILES (Isomeric): CNC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
• InChI: InChI=1S/C21H25NO5/c1-22-15-8-6-12-10-18(25-3)20(26-4)21(27-5)19(12)13-7-9-17(24-2)16(23)11-14(13)15/h7,9-11,15,22H,6,8H2,1-5H3
• InChI Key: NNJPGOLRFBJNIW-UHFFFAOYSA-N
• Popularity: 5,055 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₅NO₅
• Molecular Weight: 371.40 g/mol
• Exact Mass: 371.17327290 g/mol
• Topological Polar Surface Area (TPSA): 66.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.95
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 102491-77-0
• Demicolcine
• 1,2,3,10-Tetramethoxy-7-methylamino-6,7-dihydro-5H-benzo[a]heptalen-9-one
• NSC3096
• 6,7-Dihydro-1,2,3,10-tetramethoxy-7-(methylamino)-benzo(alpha)heptalen-9(5H)-one
• Colcemid;Colchamin;Desmecolcine;Kolchamin
• NCGC00166035-01
• MolMap_000011
• SCHEMBL8160
• CHEMBL433632
• DTXSID80859391
• HMS3374M04
• HSCI1_000384
• AKOS022144221
• SB48584
• 1,2,3,10-Tetramethoxy-7-(methylamino)-6,7-dihydrobenzo[a]heptalen-9(5H)-one
• VS-08623
• FT-0603112
• FT-0666145
• BRD-A06124629-001-01-8
• Q16959658
• 3,4,5,14-tetramethoxy-10-(methylamino)tricyclo[9.5.0.0(2),?]hexadeca-1(16),2,4,6,11,14-hexaen-13-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9966	99.66%
Caco-2	+	0.9125	91.25%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Nucleus	0.5081	50.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9352	93.52%
OATP1B3 inhibitior	+	0.9572	95.72%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8553	85.53%
P-glycoprotein inhibitior	-	0.6553	65.53%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.7177	71.77%
CYP2C9 substrate	-	0.6048	60.48%
CYP2D6 substrate	+	0.5080	50.80%
CYP3A4 inhibition	-	0.5093	50.93%
CYP2C9 inhibition	-	0.9385	93.85%
CYP2C19 inhibition	-	0.8396	83.96%
CYP2D6 inhibition	-	0.8911	89.11%
CYP1A2 inhibition	-	0.8260	82.60%
CYP2C8 inhibition	+	0.9409	94.09%
CYP inhibitory promiscuity	-	0.7928	79.28%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6931	69.31%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.8981	89.81%
Skin irritation	-	0.7134	71.34%
Skin corrosion	-	0.9277	92.77%
Ames mutagenesis	-	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7107	71.07%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	-	0.5948	59.48%
skin sensitisation	-	0.9064	90.64%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.7809	78.09%
Acute Oral Toxicity (c)	III	0.4887	48.87%
Estrogen receptor binding	+	0.9102	91.02%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.8479	84.79%
Glucocorticoid receptor binding	+	0.8970	89.70%
Aromatase binding	+	0.5460	54.60%
PPAR gamma	+	0.6869	68.69%
Honey bee toxicity	-	0.8585	85.85%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.8694	86.94%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	92.11%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.70%	96.09%
CHEMBL2535	P11166	Glucose transporter	91.40%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.02%	91.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.69%	90.71%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	90.02%	93.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.49%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.44%	95.89%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	89.17%	96.38%
CHEMBL4040	P28482	MAP kinase ERK2	87.56%	83.82%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	86.17%	96.86%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	85.76%	96.09%
CHEMBL4302	P08183	P-glycoprotein 1	85.64%	92.98%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.42%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	83.77%	91.49%
CHEMBL2803	P43403	Tyrosine-protein kinase ZAP-70	83.68%	82.50%
CHEMBL2056	P21728	Dopamine D1 receptor	83.47%	91.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	83.37%	91.79%
CHEMBL217	P14416	Dopamine D2 receptor	83.24%	95.62%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	83.24%	92.38%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.23%	97.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.94%	99.17%
CHEMBL1075317	P61964	WD repeat-containing protein 5	82.32%	96.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.99%	95.89%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.49%	96.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.79%	92.62%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.70%	96.21%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.58%	96.67%

Plants that contains it

• Calochortus venustus
• Colchicum alpinum
• Colchicum arenarium
• Colchicum autumnale
• Colchicum crocifolium
• Colchicum doerfleri
• Colchicum manissadjianii
• Colchicum ritchiei
• Colchicum robustum
• Colchicum schimperi
• Colchicum speciosum
• Colchicum szovitsii subsp. brachyphyllum
• Colchicum turcicum
• Sandersonia aurantiaca

Cross-Links

• PubChem: 2832
• LOTUS: LTS0216871
• wikiData: Q16959658