(1S)-16-methoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaen-17-ol

Details

• Internal ID: 1ee162fc-9e5e-41e8-b24b-c873f0e1b1e9
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (1S)-16-methoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaen-17-ol
• SMILES (Canonical): COC1=C(C=CC2=C1CN3CCC4=CC5=C(C=C4C3C2)OCO5)O
• SMILES (Isomeric): COC1=C(C=CC2=C1CN3CCC4=CC5=C(C=C4[C@@H]3C2)OCO5)O
• InChI: InChI=1S/C19H19NO4/c1-22-19-14-9-20-5-4-12-7-17-18(24-10-23-17)8-13(12)15(20)6-11(14)2-3-16(19)21/h2-3,7-8,15,21H,4-6,9-10H2,1H3/t15-/m0/s1
• InChI Key: TUTLRKKYUXPDGN-HNNXBMFYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₉NO₄
• Molecular Weight: 325.40 g/mol
• Exact Mass: 325.13140809 g/mol
• Topological Polar Surface Area (TPSA): 51.20 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.79
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• NSC-123389
• NCIStruc1_001545
• NCIStruc2_001901
• BDBM50429045
• CCG-37019
• NCGC00014262
• NCI123389
• NCGC00014262-02
• NCGC00097371-01

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8669	86.69%
Caco-2	+	0.8659	86.59%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.5849	58.49%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.9390	93.90%
OATP1B3 inhibitior	+	0.9414	94.14%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.7042	70.42%
P-glycoprotein inhibitior	-	0.6904	69.04%
P-glycoprotein substrate	-	0.7569	75.69%
CYP3A4 substrate	+	0.5809	58.09%
CYP2C9 substrate	-	0.6106	61.06%
CYP2D6 substrate	+	0.6924	69.24%
CYP3A4 inhibition	+	0.7667	76.67%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	+	0.8993	89.93%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	+	0.9108	91.08%
CYP2C8 inhibition	-	0.7176	71.76%
CYP inhibitory promiscuity	+	0.6666	66.66%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5422	54.22%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9463	94.63%
Skin irritation	-	0.7621	76.21%
Skin corrosion	-	0.9417	94.17%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6815	68.15%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8617	86.17%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.5986	59.86%
Acute Oral Toxicity (c)	III	0.5303	53.03%
Estrogen receptor binding	+	0.7534	75.34%
Androgen receptor binding	+	0.5280	52.80%
Thyroid receptor binding	+	0.5978	59.78%
Glucocorticoid receptor binding	+	0.7422	74.22%
Aromatase binding	-	0.5563	55.63%
PPAR gamma	+	0.6188	61.88%
Honey bee toxicity	-	0.8629	86.29%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.7217	72.17%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2056	P21728	Dopamine D1 receptor	6.3 nM; 565 nM	Ki; Ki	via Super-PRED; via Super-PRED
CHEMBL217	P14416	Dopamine D2 receptor	49.2 nM	Ki	via Super-PRED
CHEMBL234	P35462	Dopamine D3 receptor	82.4 nM	Ki	via Super-PRED
CHEMBL1850	P21918	Dopamine D5 receptor	15.1 nM	Ki	via Super-PRED
CHEMBL214	P08908	Serotonin 1a (5-HT1a) receptor	908 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.89%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	98.18%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.25%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.01%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.68%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.46%	86.33%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	88.90%	91.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.73%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.65%	98.95%
CHEMBL3438	Q05513	Protein kinase C zeta	87.24%	88.48%
CHEMBL261	P00915	Carbonic anhydrase I	86.07%	96.76%
CHEMBL2535	P11166	Glucose transporter	85.70%	98.75%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	85.44%	82.38%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	85.32%	82.67%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.99%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.58%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.43%	93.99%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	84.13%	80.96%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.89%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.11%	90.71%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.11%	80.78%
CHEMBL4208	P20618	Proteasome component C5	82.62%	90.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	81.45%	90.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.41%	85.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.08%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.72%	99.17%

Plants that contains it

• Thalictrum fendleri

Cross-Links

• PubChem: 3246443
• LOTUS: LTS0038520
• wikiData: Q105265025