Cepharadione A

Details

• Internal ID: 8f54d9b1-d06a-4223-8f4c-a75419bba018
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: 11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,12,14,16,18-heptaene-9,10-dione
• SMILES (Canonical): CN1C2=CC3=CC=CC=C3C4=C2C(=CC5=C4OCO5)C(=O)C1=O
• SMILES (Isomeric): CN1C2=CC3=CC=CC=C3C4=C2C(=CC5=C4OCO5)C(=O)C1=O
• InChI: InChI=1S/C18H11NO4/c1-19-12-6-9-4-2-3-5-10(9)15-14(12)11(16(20)18(19)21)7-13-17(15)23-8-22-13/h2-7H,8H2,1H3
• InChI Key: RZIGKFTVXWUUCX-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₁NO₄
• Molecular Weight: 305.30 g/mol
• Exact Mass: 305.06880783 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.88
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 55610-01-0
• E5UG6W56QW
• NSC 650435
• NSC-650435
• 11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,12,14,16,18-heptaene-9,10-dione
• 5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline-5,6(7H)-dione, 7-methyl-
• 5H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline-5,6(7H)-dione, 7-methyl-
• UNII-E5UG6W56QW
• CHEMBL235921
• DTXSID40970950
• CHEBI:174924
• RZIGKFTVXWUUCX-UHFFFAOYSA-N
• NSC650435
• AKOS032948952
• NCI60_017554
• 7-Methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline-5,6(7H)-dione
• 7-Methyl-2H,5H-[1,3]benzodioxolo[6,5,4-de]benzo[g]quinoline-5,6(7H)-dione
• 7-Methyl-5H-[1,3]benzodioxolo[6,5,4-de]benzo[g]quinoline-5,6(7H)-dione #
• 7-Methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline-5,6(7H)-dione, 9CI
• 11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6.0^{8,20.0^{14,19]icosa-1(20),2(6),7,12,14,16,18-heptaene-9,10-dione
• 11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6}.0^{8,20}.0^{14,19}]icosa-1,6,8(20),12,14,16,18-heptaene-9,10-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9302	93.02%
Caco-2	+	0.8128	81.28%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.4203	42.03%
OATP2B1 inhibitior	-	0.8529	85.29%
OATP1B1 inhibitior	+	0.9403	94.03%
OATP1B3 inhibitior	+	0.9541	95.41%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9598	95.98%
BSEP inhibitior	+	0.7174	71.74%
P-glycoprotein inhibitior	-	0.7208	72.08%
P-glycoprotein substrate	-	0.8663	86.63%
CYP3A4 substrate	+	0.5527	55.27%
CYP2C9 substrate	-	0.6048	60.48%
CYP2D6 substrate	-	0.8762	87.62%
CYP3A4 inhibition	-	0.5945	59.45%
CYP2C9 inhibition	-	0.6269	62.69%
CYP2C19 inhibition	+	0.5908	59.08%
CYP2D6 inhibition	-	0.7797	77.97%
CYP1A2 inhibition	+	0.8100	81.00%
CYP2C8 inhibition	-	0.8487	84.87%
CYP inhibitory promiscuity	+	0.5744	57.44%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5200	52.00%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.8660	86.60%
Skin irritation	-	0.7931	79.31%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	+	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6578	65.78%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8720	87.20%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.4932	49.32%
Acute Oral Toxicity (c)	III	0.7912	79.12%
Estrogen receptor binding	+	0.8985	89.85%
Androgen receptor binding	+	0.7586	75.86%
Thyroid receptor binding	-	0.5649	56.49%
Glucocorticoid receptor binding	+	0.7657	76.57%
Aromatase binding	+	0.7380	73.80%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9074	90.74%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.7500	75.00%
Fish aquatic toxicity	+	0.8346	83.46%

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	97.44%	95.56%
CHEMBL2581	P07339	Cathepsin D	97.16%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.23%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.43%	91.11%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	94.81%	85.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.07%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.32%	99.23%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	89.11%	98.46%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.91%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	88.28%	94.73%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	87.68%	96.67%
CHEMBL3384	Q16512	Protein kinase N1	86.61%	80.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.91%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.87%	95.83%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.67%	92.62%
CHEMBL5805	Q9NR97	Toll-like receptor 8	82.50%	96.25%
CHEMBL240	Q12809	HERG	81.52%	89.76%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.30%	93.99%

Plants that contains it

• Ardisia crispa
• Aristolochia acuminata
• Aristolochia chilensis
• Aristolochia cucurbitifolia
• Aristolochia foveolata
• Aristolochia indica
• Aristolochia kaempferi
• Aristolochia mollissima
• Aristolochia zollingeriana
• Artemisia sericea
• Doronicum grandiflorum
• Leibnitzia anandria
• Lithocarpus haipinii
• Oxytropis lanata
• Piper argyrophyllum
• Piper auritum
• Piper caninum
• Piper divaricatum
• Piper hymenophyllum
• Piper longum
• Piper methysticum
• Piper nigrum
• Piper pedicellosum
• Piper sanctum
• Piper sarmentosum
• Populus balsamifera
• Sphaerophysa salsula
• Strychnos gossweileri

Cross-Links

• PubChem: 94577
• NPASS: NPC55470
• LOTUS: LTS0083545
• wikiData: Q72516655