Cepharanone B

Details

• Internal ID: d647d193-ce08-45f3-9e84-5a43a1a86bef
• Taxonomy: Alkaloids and derivatives > Aristolactams
• IUPAC Name: 14,15-dimethoxy-10-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,8,12,14-heptaen-11-one
• InChI: InChI=1S/C17H13NO3/c1-20-13-8-11-14-12(18-17(11)19)7-9-5-3-4-6-10(9)15(14)16(13)21-2/h3-8H,1-2H3,(H,18,19)
• InChI Key: YHQIYHDLBZXUON-UHFFFAOYSA-N
• Popularity: 42 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₃NO₃
• Molecular Weight: 279.29 g/mol
• Exact Mass: 279.08954328 g/mol
• Topological Polar Surface Area (TPSA): 47.60 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.58
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• Cepharanone B
• Aristololactam bii
• 14,15-dimethoxy-10-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,8,12,14-heptaen-11-one
• 14,15-dimethoxy-10-azatetracyclo(7.6.1.02,7.012,16)hexadeca-1(16),2,4,6,8,12,14-heptaen-11-one
• RefChem:114039
• Aristolactam BII
• 1,2-dimethoxydibenzo[cd,f]indol-4(5h)-one
• Dibenz[cd,f]indol-4(5H)-one, 1,2-dimethoxy-
• Alkaloid Y, from Schefferomitra subaequalis; Aristolactam B II; Aristolactam B11; Aristololactam B II
• Dibenz(cd,f)indol-4(5H)-one, 1,2-dimethoxy-
• AristolactamBII
• Aristololactam B
• CHEMBL226772
• orb1683130
• SCHEMBL29157600
• SCHEMBL30504810
• DTXSID80968750
• DCA94809
• HY-N2893
• AKOS028108642
• 1,2-Dimethoxydibenzo[cd,f]indol-4-ol
• FS-9995
• DA-59786
• CS-0023478
• B0005-189390
• 14,15-dimethoxy-10-azatetracyclo[7.6.1.0^{2,7.0^{12,16]hexadeca-1(16),2,4,6,8,12,14-heptaen-11-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8892	88.92%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6840	68.40%
OATP2B1 inhibitior	-	0.8627	86.27%
OATP1B1 inhibitior	+	0.9366	93.66%
OATP1B3 inhibitior	+	0.9636	96.36%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7416	74.16%
P-glycoprotein inhibitior	-	0.6570	65.70%
P-glycoprotein substrate	-	0.8266	82.66%
CYP3A4 substrate	+	0.5911	59.11%
CYP2C9 substrate	-	0.8100	81.00%
CYP2D6 substrate	-	0.8274	82.74%
CYP3A4 inhibition	+	0.5218	52.18%
CYP2C9 inhibition	-	0.7255	72.55%
CYP2C19 inhibition	-	0.7386	73.86%
CYP2D6 inhibition	-	0.9118	91.18%
CYP1A2 inhibition	+	0.9770	97.70%
CYP2C8 inhibition	-	0.5957	59.57%
CYP inhibitory promiscuity	+	0.7921	79.21%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.4118	41.18%
Eye corrosion	-	0.9905	99.05%
Eye irritation	+	0.5731	57.31%
Skin irritation	-	0.8184	81.84%
Skin corrosion	-	0.9771	97.71%
Ames mutagenesis	+	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4712	47.12%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.9458	94.58%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.6292	62.92%
Acute Oral Toxicity (c)	III	0.4514	45.14%
Estrogen receptor binding	+	0.8079	80.79%
Androgen receptor binding	+	0.7384	73.84%
Thyroid receptor binding	+	0.6797	67.97%
Glucocorticoid receptor binding	+	0.8762	87.62%
Aromatase binding	+	0.7957	79.57%
PPAR gamma	+	0.6803	68.03%
Honey bee toxicity	-	0.8388	83.88%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	+	0.8190	81.90%

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	98.12%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.51%	95.56%
CHEMBL4302	P08183	P-glycoprotein 1	94.89%	92.98%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.45%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	93.20%	94.75%
CHEMBL2535	P11166	Glucose transporter	92.84%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.22%	86.33%
CHEMBL1907	P15144	Aminopeptidase N	88.33%	93.31%
CHEMBL2581	P07339	Cathepsin D	87.88%	98.95%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	85.93%	96.67%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.55%	96.09%
CHEMBL4208	P20618	Proteasome component C5	85.21%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.95%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.54%	93.99%
CHEMBL1255126	O15151	Protein Mdm4	83.25%	90.20%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	82.68%	85.49%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.09%	92.62%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	81.71%	81.14%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.52%	94.08%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.35%	82.69%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.24%	96.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.18%	93.03%

Plants that contains it

• Aristolochia baetica
• Aristolochia constricta
• Aristolochia cucurbitifolia
• Aristolochia didyma
• Aristolochia kaempferi
• Aristolochia manshuriensis
• Artemisia sericea
• Curcuma zedoaria
• Fissistigma balansae
• Fissistigma glaucescens
• Fissistigma oldhamii
• Goniothalamus amuyon
• Goniothalamus griffithii
• Goniothalamus velutinus
• Houttuynia cordata
• Metanarthecium luteoviride
• Pandanus tectorius
• Piper argyrophyllum
• Piper auritum
• Piper longum
• Piper macropiper
• Piper swartzianum
• Sarcococca saligna
• Saururus cernuus
• Saururus chinensis
• Stephania cephalantha
• Uvaria hamiltonii
• Uvaria littoralis

Cross-Links

• PubChem: 162739
• NPASS: NPC265383
• ChEMBL: CHEMBL226772
• LOTUS: LTS0198242
• wikiData: Q72443751