(1R)-1-butoxy-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaene-14,21-dione

Details

• Internal ID: d608c0fb-a14a-4cf3-9d47-de3cb662cae3
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (1R)-1-butoxy-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaene-14,21-dione
• SMILES (Canonical): CCCCOC12C3=CC4=C(C=C3CCN1C(=O)C5=C(C2=O)C=CC(=C5OC)OC)OCO4
• SMILES (Isomeric): CCCCO[C@@]12C3=CC4=C(C=C3CCN1C(=O)C5=C(C2=O)C=CC(=C5OC)OC)OCO4
• InChI: InChI=1S/C24H25NO7/c1-4-5-10-32-24-16-12-19-18(30-13-31-19)11-14(16)8-9-25(24)23(27)20-15(22(24)26)6-7-17(28-2)21(20)29-3/h6-7,11-12H,4-5,8-10,13H2,1-3H3/t24-/m1/s1
• InChI Key: OJLHNHDUDBFJBQ-XMMPIXPASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₅NO₇
• Molecular Weight: 439.50 g/mol
• Exact Mass: 439.16310214 g/mol
• Topological Polar Surface Area (TPSA): 83.50 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.30
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8741	87.41%
Caco-2	+	0.7075	70.75%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5259	52.59%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8924	89.24%
OATP1B3 inhibitior	+	0.9357	93.57%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8833	88.33%
P-glycoprotein inhibitior	+	0.8551	85.51%
P-glycoprotein substrate	+	0.5565	55.65%
CYP3A4 substrate	+	0.6678	66.78%
CYP2C9 substrate	-	0.7983	79.83%
CYP2D6 substrate	-	0.8216	82.16%
CYP3A4 inhibition	+	0.7589	75.89%
CYP2C9 inhibition	-	0.6447	64.47%
CYP2C19 inhibition	+	0.5205	52.05%
CYP2D6 inhibition	-	0.8840	88.40%
CYP1A2 inhibition	-	0.8363	83.63%
CYP2C8 inhibition	+	0.5668	56.68%
CYP inhibitory promiscuity	+	0.5879	58.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5537	55.37%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9288	92.88%
Skin irritation	-	0.8177	81.77%
Skin corrosion	-	0.9413	94.13%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5668	56.68%
Micronuclear	+	0.7074	70.74%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8859	88.59%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.7606	76.06%
Acute Oral Toxicity (c)	III	0.7310	73.10%
Estrogen receptor binding	+	0.8097	80.97%
Androgen receptor binding	+	0.7004	70.04%
Thyroid receptor binding	+	0.5340	53.40%
Glucocorticoid receptor binding	+	0.8308	83.08%
Aromatase binding	-	0.4944	49.44%
PPAR gamma	+	0.7191	71.91%
Honey bee toxicity	-	0.8923	89.23%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.8609	86.09%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.22%	83.82%
CHEMBL2581	P07339	Cathepsin D	97.84%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.39%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.32%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.78%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.93%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	95.36%	93.40%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	95.07%	80.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.59%	95.56%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	92.97%	82.38%
CHEMBL4208	P20618	Proteasome component C5	92.64%	90.00%
CHEMBL261	P00915	Carbonic anhydrase I	92.29%	96.76%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.87%	92.62%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	89.90%	82.67%
CHEMBL240	Q12809	HERG	88.77%	89.76%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.70%	99.17%
CHEMBL5979	P05186	Alkaline phosphatase, tissue-nonspecific isozyme	86.56%	85.40%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.30%	90.71%
CHEMBL3891	P07384	Calpain 1	85.09%	93.04%
CHEMBL1907	P15144	Aminopeptidase N	84.12%	93.31%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.95%	94.00%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	83.86%	92.08%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.63%	95.89%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	82.79%	96.25%
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	82.40%	95.52%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.26%	96.21%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	81.05%	95.53%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.98%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.54%	94.45%
CHEMBL5747	Q92793	CREB-binding protein	80.51%	95.12%

Plants that contains it

• Phellodendron chinense

Cross-Links

• PubChem: 162967522
• LOTUS: LTS0041863
• wikiData: Q105193142