12,14-Dimethoxy-3,5-dioxa-10-azapentacyclo[9.7.1.02,6.08,19.013,18]nonadeca-1(19),2(6),7,11,13(18),14,16-heptaen-9-one

Details

• Internal ID: 045c781a-785a-47a9-94f2-0377103494a5
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Phenanthrols
• IUPAC Name: 12,14-dimethoxy-3,5-dioxa-10-azapentacyclo[9.7.1.02,6.08,19.013,18]nonadeca-1(19),2(6),7,11,13(18),14,16-heptaen-9-one
• SMILES (Canonical): COC1=CC=CC2=C1C(=C3C4=C2C5=C(C=C4C(=O)N3)OCO5)OC
• SMILES (Isomeric): COC1=CC=CC2=C1C(=C3C4=C2C5=C(C=C4C(=O)N3)OCO5)OC
• InChI: InChI=1S/C18H13NO5/c1-21-10-5-3-4-8-12(10)17(22-2)15-13-9(18(20)19-15)6-11-16(14(8)13)24-7-23-11/h3-6H,7H2,1-2H3,(H,19,20)
• InChI Key: LGDDKZBOKLRXPS-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₃NO₅
• Molecular Weight: 323.30 g/mol
• Exact Mass: 323.07937252 g/mol
• Topological Polar Surface Area (TPSA): 66.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.30
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9908	99.08%
Caco-2	+	0.8140	81.40%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5076	50.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9422	94.22%
OATP1B3 inhibitior	+	0.9363	93.63%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8546	85.46%
P-glycoprotein inhibitior	-	0.6079	60.79%
P-glycoprotein substrate	-	0.6981	69.81%
CYP3A4 substrate	+	0.6481	64.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8485	84.85%
CYP3A4 inhibition	+	0.8570	85.70%
CYP2C9 inhibition	+	0.6935	69.35%
CYP2C19 inhibition	+	0.5608	56.08%
CYP2D6 inhibition	-	0.7896	78.96%
CYP1A2 inhibition	+	0.8765	87.65%
CYP2C8 inhibition	-	0.6625	66.25%
CYP inhibitory promiscuity	+	0.8803	88.03%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5707	57.07%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.7254	72.54%
Skin irritation	-	0.8093	80.93%
Skin corrosion	-	0.9620	96.20%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4335	43.35%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8383	83.83%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.4739	47.39%
Acute Oral Toxicity (c)	III	0.5771	57.71%
Estrogen receptor binding	+	0.8786	87.86%
Androgen receptor binding	+	0.5647	56.47%
Thyroid receptor binding	+	0.6462	64.62%
Glucocorticoid receptor binding	+	0.8548	85.48%
Aromatase binding	+	0.6643	66.43%
PPAR gamma	+	0.8005	80.05%
Honey bee toxicity	-	0.7962	79.62%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.7701	77.01%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.59%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.48%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.55%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.82%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	95.24%	94.80%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.59%	94.00%
CHEMBL2535	P11166	Glucose transporter	94.53%	98.75%
CHEMBL2581	P07339	Cathepsin D	93.21%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.82%	89.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.55%	93.99%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.98%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.66%	86.33%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	91.64%	80.96%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.14%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.90%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.32%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.31%	95.89%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	84.60%	85.00%
CHEMBL1937	Q92769	Histone deacetylase 2	84.51%	94.75%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.16%	82.67%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	84.08%	92.38%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	83.53%	94.03%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.47%	96.21%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.45%	97.14%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	83.41%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.23%	85.14%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.28%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.89%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.77%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.70%	97.09%
CHEMBL213	P08588	Beta-1 adrenergic receptor	80.21%	95.56%

Plants that contains it

• Aristolochia auricularia
• Aristolochia cucurbitifolia
• Aristolochia kaempferi
• Aristolochia manshuriensis
• Aristolochia mollissima
• Aristolochia pontica
• Aristolochia zollingeriana

Cross-Links

• PubChem: 14804089
• LOTUS: LTS0061136
• wikiData: Q104397326