N-(2,3-Dihydroxy-1,10-dimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide

Details

• Internal ID: dd2c1958-d1ac-4bfb-9a73-252aa80ddbe3
• Taxonomy: Hydrocarbon derivatives > Tropones
• IUPAC Name: N-(2,3-dihydroxy-1,10-dimethoxy-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)O
• SMILES (Isomeric): CC(=O)NC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)O)O
• InChI: InChI=1S/C20H21NO6/c1-10(22)21-14-6-4-11-8-16(24)19(25)20(27-3)18(11)12-5-7-17(26-2)15(23)9-13(12)14/h5,7-9,14,24-25H,4,6H2,1-3H3,(H,21,22)
• InChI Key: DEIXKZGDCOFYAR-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₁NO₆
• Molecular Weight: 371.40 g/mol
• Exact Mass: 371.13688739 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 2.27
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• N-(2,3-Dihydroxy-1,10-dimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl)acetamide
• NSC354974
• N-(2,3-dihydroxy-1,10-dimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl)acetamide
• 2,3-Didemethylcolchicine
• 2,3-Dimethylcolchicine
• NSC 354974
• 2,3-Dedimethylcolchicine
• 2,3-didemethyl-colchicine
• CHEMBL1984076
• DEIXKZGDCOFYAR-UHFFFAOYSA-N
• DTXSID901125731
• NSC-354974
• 102491-81-6
• Acetamide, N-(5,6,7,9-tetrahydro-2,3-dihydroxy-1,10-dimethoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)-
• Acetamide, N-(5,6,7,9-tetrahydro-2,3-dihydroxy-1,10-dimethyoxy-9-oxobenzo(a)heptalen-7-yl)-, (S)-
• N-(5,6,7,9-Tetrahydro-2,3-dihydroxy-1,10-dimethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide
• Acetamide, N-(5,6,7,9-tetrahydro-2,3-dihydroxy-1, {10-dimethoxy-9-oxobenzo[a]heptalen-7-yl)-,} (S)-
• Acetamide,6,7,9-tetrahydro-2,3-dihydroxy-1,10-dimethoxy-9-oxobenzo[a]heptalen-7-yl)-, (S)-
• N-(2,3-Dihydroxy-1,10-dimethoxy-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	+	0.8487	84.87%
Caco-2	-	0.5780	57.80%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Nucleus	0.5678	56.78%
OATP2B1 inhibitior	-	0.8664	86.64%
OATP1B1 inhibitior	+	0.9126	91.26%
OATP1B3 inhibitior	+	0.9488	94.88%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9393	93.93%
BSEP inhibitior	+	0.6443	64.43%
P-glycoprotein inhibitior	-	0.8256	82.56%
P-glycoprotein substrate	+	0.9382	93.82%
CYP3A4 substrate	+	0.7255	72.55%
CYP2C9 substrate	-	0.8337	83.37%
CYP2D6 substrate	-	0.8284	82.84%
CYP3A4 inhibition	-	0.8948	89.48%
CYP2C9 inhibition	-	0.9085	90.85%
CYP2C19 inhibition	-	0.9290	92.90%
CYP2D6 inhibition	-	0.9232	92.32%
CYP1A2 inhibition	-	0.9086	90.86%
CYP2C8 inhibition	+	0.9574	95.74%
CYP inhibitory promiscuity	-	0.9386	93.86%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6771	67.71%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.8650	86.50%
Skin irritation	-	0.7727	77.27%
Skin corrosion	-	0.9370	93.70%
Ames mutagenesis	-	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4288	42.88%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.6897	68.97%
skin sensitisation	-	0.9143	91.43%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.6033	60.33%
Estrogen receptor binding	+	0.7755	77.55%
Androgen receptor binding	+	0.8352	83.52%
Thyroid receptor binding	+	0.6133	61.33%
Glucocorticoid receptor binding	+	0.7915	79.15%
Aromatase binding	-	0.5640	56.40%
PPAR gamma	+	0.7338	73.38%
Honey bee toxicity	-	0.9021	90.21%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.8055	80.55%

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	99.19%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.87%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.53%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.96%	85.14%
CHEMBL2581	P07339	Cathepsin D	93.66%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.99%	90.71%
CHEMBL2056	P21728	Dopamine D1 receptor	91.35%	91.00%
CHEMBL217	P14416	Dopamine D2 receptor	90.95%	95.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.37%	99.17%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.89%	96.38%
CHEMBL340	P08684	Cytochrome P450 3A4	88.60%	91.19%
CHEMBL2535	P11166	Glucose transporter	88.50%	98.75%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.42%	93.03%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.87%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.90%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.69%	95.89%
CHEMBL4208	P20618	Proteasome component C5	84.68%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.69%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.59%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.55%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.41%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.05%	96.21%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.30%	95.64%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.72%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.46%	86.33%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	80.86%	91.79%

Plants that contains it

• Colchicum bivonae

Cross-Links

• PubChem: 100173
• LOTUS: LTS0066164
• wikiData: Q104977278