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

Details

• Internal ID: 3f44c2fc-83c9-4762-aea8-0da11d1333cd
• Taxonomy: Hydrocarbon derivatives > Tropones > Tropolones
• IUPAC Name: (7S)-10-hydroxy-1,2,3-trimethoxy-7-(methylamino)-6,7-dihydro-5H-benzo[a]heptalen-9-one
• SMILES (Canonical): CNC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)O)OC)OC)OC
• SMILES (Isomeric): CN[C@H]1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)O)OC)OC)OC
• InChI: InChI=1S/C20H23NO5/c1-21-14-7-5-11-9-17(24-2)19(25-3)20(26-4)18(11)12-6-8-15(22)16(23)10-13(12)14/h6,8-10,14,21H,5,7H2,1-4H3,(H,22,23)/t14-/m0/s1
• InChI Key: ATWWYGQDYGSWQA-AWEZNQCLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₃NO₅
• Molecular Weight: 357.40 g/mol
• Exact Mass: 357.15762283 g/mol
• Topological Polar Surface Area (TPSA): 77.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 2.65
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 518-11-6
• (7S)-10-hydroxy-1,2,3-trimethoxy-7-(methylamino)-6,7-dihydro-5H-benzo[a]heptalen-9-one
• CHEMBL327221
• DTXSID50199731
• NSC36559
• NSC-36559
• AKOS030254311

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9910	99.10%
Caco-2	+	0.8248	82.48%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Nucleus	0.6829	68.29%
OATP2B1 inhibitior	-	0.8681	86.81%
OATP1B1 inhibitior	+	0.9350	93.50%
OATP1B3 inhibitior	+	0.9409	94.09%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7105	71.05%
P-glycoprotein inhibitior	-	0.8002	80.02%
P-glycoprotein substrate	+	0.8599	85.99%
CYP3A4 substrate	+	0.6909	69.09%
CYP2C9 substrate	-	0.6039	60.39%
CYP2D6 substrate	+	0.4688	46.88%
CYP3A4 inhibition	-	0.6436	64.36%
CYP2C9 inhibition	-	0.9264	92.64%
CYP2C19 inhibition	-	0.8794	87.94%
CYP2D6 inhibition	-	0.8874	88.74%
CYP1A2 inhibition	-	0.8715	87.15%
CYP2C8 inhibition	+	0.8991	89.91%
CYP inhibitory promiscuity	-	0.8869	88.69%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.7004	70.04%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.8711	87.11%
Skin irritation	-	0.7192	71.92%
Skin corrosion	-	0.9207	92.07%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4928	49.28%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.6040	60.40%
skin sensitisation	-	0.8850	88.50%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6930	69.30%
Acute Oral Toxicity (c)	III	0.5301	53.01%
Estrogen receptor binding	+	0.8247	82.47%
Androgen receptor binding	+	0.8439	84.39%
Thyroid receptor binding	+	0.8220	82.20%
Glucocorticoid receptor binding	+	0.8886	88.86%
Aromatase binding	+	0.5242	52.42%
PPAR gamma	+	0.7084	70.84%
Honey bee toxicity	-	0.8825	88.25%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5051	50.51%
Fish aquatic toxicity	+	0.8395	83.95%

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	98.72%	91.11%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	96.70%	91.79%
CHEMBL2535	P11166	Glucose transporter	94.16%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.94%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	92.14%	90.71%
CHEMBL217	P14416	Dopamine D2 receptor	91.93%	95.62%
CHEMBL2581	P07339	Cathepsin D	91.86%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.86%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	90.05%	91.49%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.57%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.71%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.20%	93.99%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.11%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.09%	85.14%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.24%	91.03%
CHEMBL2056	P21728	Dopamine D1 receptor	84.88%	91.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.25%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.74%	86.33%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	83.60%	96.86%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.98%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.65%	99.23%
CHEMBL3438	Q05513	Protein kinase C zeta	82.18%	88.48%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.40%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.30%	92.62%
CHEMBL2803	P43403	Tyrosine-protein kinase ZAP-70	81.29%	82.50%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.29%	96.00%

Plants that contains it

• Colchicum ritchiei

Cross-Links

• PubChem: 235315
• LOTUS: LTS0115673
• wikiData: Q83072681