(12S)-16-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaen-17-ol

Details

• Internal ID: 1ff40804-b754-4382-9e0f-7463b10aa057
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: (12S)-16-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaen-17-ol
• SMILES (Canonical): COC1=C(C=C2C(=C1)CC3C4=C2C5=C(C=C4CCN3)OCO5)O
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C[C@H]3C4=C2C5=C(C=C4CCN3)OCO5)O
• InChI: InChI=1S/C18H17NO4/c1-21-14-6-10-4-12-16-9(2-3-19-12)5-15-18(23-8-22-15)17(16)11(10)7-13(14)20/h5-7,12,19-20H,2-4,8H2,1H3/t12-/m0/s1
• InChI Key: NWCGFAYLTGJNLQ-LBPRGKRZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₇NO₄
• Molecular Weight: 311.30 g/mol
• Exact Mass: 311.11575802 g/mol
• Topological Polar Surface Area (TPSA): 60.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.54
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9540	95.40%
Caco-2	+	0.8177	81.77%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5361	53.61%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.9035	90.35%
OATP1B3 inhibitior	+	0.9531	95.31%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6117	61.17%
P-glycoprotein inhibitior	-	0.7853	78.53%
P-glycoprotein substrate	-	0.6764	67.64%
CYP3A4 substrate	+	0.5896	58.96%
CYP2C9 substrate	-	0.8216	82.16%
CYP2D6 substrate	+	0.6215	62.15%
CYP3A4 inhibition	+	0.5242	52.42%
CYP2C9 inhibition	-	0.8569	85.69%
CYP2C19 inhibition	-	0.5508	55.08%
CYP2D6 inhibition	+	0.6539	65.39%
CYP1A2 inhibition	+	0.6365	63.65%
CYP2C8 inhibition	+	0.5203	52.03%
CYP inhibitory promiscuity	+	0.5656	56.56%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6052	60.52%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.8393	83.93%
Skin irritation	-	0.7289	72.89%
Skin corrosion	-	0.9375	93.75%
Ames mutagenesis	+	0.6146	61.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.3846	38.46%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.8314	83.14%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6260	62.60%
Acute Oral Toxicity (c)	III	0.5742	57.42%
Estrogen receptor binding	+	0.8405	84.05%
Androgen receptor binding	-	0.5655	56.55%
Thyroid receptor binding	+	0.7620	76.20%
Glucocorticoid receptor binding	+	0.7317	73.17%
Aromatase binding	+	0.6491	64.91%
PPAR gamma	+	0.7971	79.71%
Honey bee toxicity	-	0.7900	79.00%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5249	52.49%
Fish aquatic toxicity	-	0.5000	50.00%

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	98.63%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.74%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.53%	96.77%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	94.10%	95.55%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.80%	97.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.06%	93.99%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	92.85%	91.79%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	91.51%	82.67%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.45%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.32%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.32%	92.94%
CHEMBL3438	Q05513	Protein kinase C zeta	91.26%	88.48%
CHEMBL1951	P21397	Monoamine oxidase A	90.86%	91.49%
CHEMBL2581	P07339	Cathepsin D	89.85%	98.95%
CHEMBL4208	P20618	Proteasome component C5	89.80%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.63%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.11%	96.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.41%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.81%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.35%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.73%	99.17%
CHEMBL213	P08588	Beta-1 adrenergic receptor	85.72%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.47%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.36%	96.95%
CHEMBL2535	P11166	Glucose transporter	83.86%	98.75%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	83.38%	96.86%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.30%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.24%	95.56%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	82.81%	80.96%
CHEMBL5543	Q9Y463	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	81.97%	94.70%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.85%	95.78%

Plants that contains it

• Annona hayesii
• Stephania cephalantha

Cross-Links

• PubChem: 13891936
• LOTUS: LTS0214191
• wikiData: Q105186532