5,6,17-Trimethoxy-11-methyl-2-oxa-11-azatetracyclo[8.7.1.03,8.014,18]octadeca-1(17),3,5,7,14(18),15-hexaene

Details

• Internal ID: 237c7f63-770e-4beb-bcc5-dadfe59dce40
• Taxonomy: Alkaloids and derivatives > Cularin alkaloids and derivatives
• IUPAC Name: 5,6,17-trimethoxy-11-methyl-2-oxa-11-azatetracyclo[8.7.1.03,8.014,18]octadeca-1(17),3,5,7,14(18),15-hexaene
• SMILES (Canonical): CN1CCC2=C3C1CC4=CC(=C(C=C4OC3=C(C=C2)OC)OC)OC
• SMILES (Isomeric): CN1CCC2=C3C1CC4=CC(=C(C=C4OC3=C(C=C2)OC)OC)OC
• InChI: InChI=1S/C20H23NO4/c1-21-8-7-12-5-6-15(22-2)20-19(12)14(21)9-13-10-17(23-3)18(24-4)11-16(13)25-20/h5-6,10-11,14H,7-9H2,1-4H3
• InChI Key: DTMXRZMJFCVJQS-UHFFFAOYSA-N
• Popularity: 43 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.40 g/mol
• Exact Mass: 341.16270821 g/mol
• Topological Polar Surface Area (TPSA): 40.20 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.59
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• SCHEMBL679676
• AC1Q58B0
• AR-1C3196

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9190	91.90%
Caco-2	+	0.9514	95.14%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Lysosomes	0.5282	52.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9490	94.90%
OATP1B3 inhibitior	+	0.9486	94.86%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.8272	82.72%
P-glycoprotein inhibitior	+	0.5862	58.62%
P-glycoprotein substrate	-	0.5408	54.08%
CYP3A4 substrate	+	0.5999	59.99%
CYP2C9 substrate	+	0.7825	78.25%
CYP2D6 substrate	+	0.8198	81.98%
CYP3A4 inhibition	-	0.7866	78.66%
CYP2C9 inhibition	-	0.9168	91.68%
CYP2C19 inhibition	-	0.8465	84.65%
CYP2D6 inhibition	-	0.6586	65.86%
CYP1A2 inhibition	-	0.7619	76.19%
CYP2C8 inhibition	-	0.8347	83.47%
CYP inhibitory promiscuity	-	0.9567	95.67%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6558	65.58%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9793	97.93%
Skin irritation	-	0.7891	78.91%
Skin corrosion	-	0.9475	94.75%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8383	83.83%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.7841	78.41%
skin sensitisation	-	0.8798	87.98%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8899	88.99%
Acute Oral Toxicity (c)	III	0.7222	72.22%
Estrogen receptor binding	+	0.6170	61.70%
Androgen receptor binding	-	0.5286	52.86%
Thyroid receptor binding	+	0.6492	64.92%
Glucocorticoid receptor binding	+	0.7734	77.34%
Aromatase binding	-	0.6305	63.05%
PPAR gamma	+	0.5895	58.95%
Honey bee toxicity	-	0.8731	87.31%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.7400	74.00%
Fish aquatic toxicity	+	0.8847	88.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.01%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	94.06%	93.99%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	93.46%	93.40%
CHEMBL217	P14416	Dopamine D2 receptor	92.82%	95.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.03%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.35%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.21%	86.33%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	89.21%	90.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.93%	95.89%
CHEMBL261	P00915	Carbonic anhydrase I	87.60%	96.76%
CHEMBL2056	P21728	Dopamine D1 receptor	87.58%	91.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.42%	94.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.68%	95.78%
CHEMBL2581	P07339	Cathepsin D	84.59%	98.95%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	84.44%	96.86%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.16%	89.62%
CHEMBL2535	P11166	Glucose transporter	83.98%	98.75%
CHEMBL5747	Q92793	CREB-binding protein	82.34%	95.12%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.72%	92.38%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.46%	85.14%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	81.42%	95.53%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.12%	93.65%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.62%	100.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.17%	82.38%

Plants that contains it

• Ceratocapnos claviculata
• Sarcocapnos crassifolia

Cross-Links

• PubChem: 629876
• NPASS: NPC200545
• LOTUS: LTS0275525
• wikiData: Q6419667