Norcepharadione B

Details

• Internal ID: ab1b8604-07b2-49e4-81d4-bce611d57d07
• Taxonomy: Alkaloids and derivatives > Aporphines > 4,5-dioxoaporphines
• IUPAC Name: 15,16-dimethoxy-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione
• SMILES (Canonical): COC1=C(C2=C3C(=C1)C(=O)C(=O)NC3=CC4=CC=CC=C42)OC
• SMILES (Isomeric): COC1=C(C2=C3C(=C1)C(=O)C(=O)NC3=CC4=CC=CC=C42)OC
• InChI: InChI=1S/C18H13NO4/c1-22-13-8-11-14-12(19-18(21)16(11)20)7-9-5-3-4-6-10(9)15(14)17(13)23-2/h3-8H,1-2H3,(H,19,21)
• InChI Key: BAGGDUOPTSQTHD-UHFFFAOYSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₃NO₄
• Molecular Weight: 307.30 g/mol
• Exact Mass: 307.08445790 g/mol
• Topological Polar Surface Area (TPSA): 64.60 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.15
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 57576-41-7
• norcepharadione
• NorcepharadioneB
• 4H-Dibenzo[de,g]quinoline-4,5(6H)-dione, 1,2-dimethoxy-
• 15,16-dimethoxy-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione
• 1,2-Dimethoxy-4H-dibenzo[de,g]quinoline-4,5(6H)-dione; Norcepharadione
• CHEMBL227414
• DTXSID80206205
• AKOS028108617
• 15,16-dimethoxy-10-azatetracyclo[7.7.1.0^{2,7.0^{13,17]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9797	97.97%
Caco-2	+	0.8769	87.69%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6197	61.97%
OATP2B1 inhibitior	-	0.8607	86.07%
OATP1B1 inhibitior	+	0.9395	93.95%
OATP1B3 inhibitior	+	0.9710	97.10%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7146	71.46%
P-glycoprotein inhibitior	-	0.6153	61.53%
P-glycoprotein substrate	-	0.8264	82.64%
CYP3A4 substrate	+	0.5868	58.68%
CYP2C9 substrate	-	0.8100	81.00%
CYP2D6 substrate	-	0.8274	82.74%
CYP3A4 inhibition	-	0.6478	64.78%
CYP2C9 inhibition	-	0.7594	75.94%
CYP2C19 inhibition	-	0.9213	92.13%
CYP2D6 inhibition	-	0.9583	95.83%
CYP1A2 inhibition	+	0.8506	85.06%
CYP2C8 inhibition	-	0.5988	59.88%
CYP inhibitory promiscuity	-	0.5437	54.37%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6445	64.45%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.6844	68.44%
Skin irritation	-	0.8550	85.50%
Skin corrosion	-	0.9760	97.60%
Ames mutagenesis	+	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4562	45.62%
Micronuclear	+	0.7659	76.59%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.9684	96.84%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.5815	58.15%
Acute Oral Toxicity (c)	III	0.6030	60.30%
Estrogen receptor binding	+	0.8601	86.01%
Androgen receptor binding	+	0.7578	75.78%
Thyroid receptor binding	+	0.6136	61.36%
Glucocorticoid receptor binding	+	0.8222	82.22%
Aromatase binding	+	0.7422	74.22%
PPAR gamma	+	0.6367	63.67%
Honey bee toxicity	-	0.8337	83.37%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	0.6598	65.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.26%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.08%	91.11%
CHEMBL4302	P08183	P-glycoprotein 1	95.03%	92.98%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.95%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	91.37%	94.75%
CHEMBL2535	P11166	Glucose transporter	90.76%	98.75%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	89.28%	96.67%
CHEMBL2581	P07339	Cathepsin D	89.16%	98.95%
CHEMBL1907	P15144	Aminopeptidase N	87.54%	93.31%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.70%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.56%	86.33%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	85.56%	85.49%
CHEMBL3524	P56524	Histone deacetylase 4	85.22%	92.97%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.36%	96.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.96%	93.03%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.64%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.55%	85.14%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	82.91%	81.14%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	82.86%	94.08%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.84%	95.83%
CHEMBL4208	P20618	Proteasome component C5	82.78%	90.00%
CHEMBL1255126	O15151	Protein Mdm4	82.51%	90.20%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.47%	93.99%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.33%	94.62%
CHEMBL3401	O75469	Pregnane X receptor	82.18%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.92%	89.00%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	80.65%	96.47%

Plants that contains it

• Annona squamosa
• Fissistigma balansae
• Fissistigma glaucescens
• Fissistigma oldhamii
• Houttuynia cordata
• Piper longum
• Telitoxicum krukovii

Cross-Links

• PubChem: 189168
• NPASS: NPC222561
• ChEMBL: CHEMBL227414
• LOTUS: LTS0160285
• wikiData: Q72496812