N-(3-hydroxy-1,2,10-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl)formamide

Details

• Internal ID: d3888607-e75d-4cbb-a46e-6a945fd86dad
• Taxonomy: Hydrocarbon derivatives > Tropones
• IUPAC Name: N-(3-hydroxy-1,2,10-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl)formamide
• SMILES (Canonical): COC1=CC=C2C(=CC1=O)C(CCC3=CC(=C(C(=C32)OC)OC)O)NC=O
• SMILES (Isomeric): COC1=CC=C2C(=CC1=O)C(CCC3=CC(=C(C(=C32)OC)OC)O)NC=O
• InChI: InChI=1S/C20H21NO6/c1-25-17-7-5-12-13(9-15(17)23)14(21-10-22)6-4-11-8-16(24)19(26-2)20(27-3)18(11)12/h5,7-10,14,24H,4,6H2,1-3H3,(H,21,22)
• InChI Key: NARFZZQNNQGPBJ-UHFFFAOYSA-N
• Popularity: 0 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): 94.10 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 2.18
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• NSC180534
• SCHEMBL3147945
• DTXSID70306829
• NSC-180534
• N-(3-hydroxy-1,2,10-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl)formamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9443	94.43%
Caco-2	+	0.7347	73.47%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Nucleus	0.6307	63.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9013	90.13%
OATP1B3 inhibitior	+	0.9431	94.31%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9643	96.43%
BSEP inhibitior	+	0.8398	83.98%
P-glycoprotein inhibitior	-	0.6490	64.90%
P-glycoprotein substrate	+	0.8426	84.26%
CYP3A4 substrate	+	0.6950	69.50%
CYP2C9 substrate	-	0.8411	84.11%
CYP2D6 substrate	-	0.7960	79.60%
CYP3A4 inhibition	-	0.8698	86.98%
CYP2C9 inhibition	-	0.9317	93.17%
CYP2C19 inhibition	-	0.9132	91.32%
CYP2D6 inhibition	-	0.9103	91.03%
CYP1A2 inhibition	-	0.8940	89.40%
CYP2C8 inhibition	+	0.8916	89.16%
CYP inhibitory promiscuity	-	0.9064	90.64%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9411	94.11%
Carcinogenicity (trinary)	Non-required	0.6724	67.24%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9016	90.16%
Skin irritation	-	0.7652	76.52%
Skin corrosion	-	0.9353	93.53%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4831	48.31%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.5323	53.23%
skin sensitisation	-	0.9279	92.79%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5620	56.20%
Acute Oral Toxicity (c)	III	0.5388	53.88%
Estrogen receptor binding	+	0.7710	77.10%
Androgen receptor binding	+	0.7971	79.71%
Thyroid receptor binding	+	0.7573	75.73%
Glucocorticoid receptor binding	+	0.8648	86.48%
Aromatase binding	-	0.5707	57.07%
PPAR gamma	+	0.7165	71.65%
Honey bee toxicity	-	0.8822	88.22%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8031	80.31%

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	97.98%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.96%	91.49%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	95.00%	91.79%
CHEMBL2581	P07339	Cathepsin D	93.73%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.76%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.90%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.31%	90.71%
CHEMBL2535	P11166	Glucose transporter	91.12%	98.75%
CHEMBL4208	P20618	Proteasome component C5	90.42%	90.00%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	88.57%	98.11%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.45%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.38%	95.89%
CHEMBL217	P14416	Dopamine D2 receptor	88.27%	95.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.70%	99.17%
CHEMBL2056	P21728	Dopamine D1 receptor	87.37%	91.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.94%	86.33%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	85.71%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.61%	93.40%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.29%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.37%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.03%	91.07%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.74%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.89%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.78%	85.14%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	81.23%	96.86%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.20%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.75%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	80.02%	91.19%

Plants that contains it

• Colchicum autumnale
• Colchicum bivonae

Cross-Links

• PubChem: 301815
• LOTUS: LTS0256074
• wikiData: Q82054120