Papaveraldine

Details

• Internal ID: a4e29a1c-93a8-4705-bedb-9559479419f2
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Benzylisoquinolines
• IUPAC Name: (6,7-dimethoxyisoquinolin-1-yl)-(3,4-dimethoxyphenyl)methanone
• SMILES (Canonical): COC1=C(C=C(C=C1)C(=O)C2=NC=CC3=CC(=C(C=C32)OC)OC)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)C(=O)C2=NC=CC3=CC(=C(C=C32)OC)OC)OC
• InChI: InChI=1S/C20H19NO5/c1-23-15-6-5-13(10-16(15)24-2)20(22)19-14-11-18(26-4)17(25-3)9-12(14)7-8-21-19/h5-11H,1-4H3
• InChI Key: QJTBIAMBPGGIGI-UHFFFAOYSA-N
• Popularity: 95 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₉NO₅
• Molecular Weight: 353.40 g/mol
• Exact Mass: 353.12632271 g/mol
• Topological Polar Surface Area (TPSA): 66.90 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.50
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• Xanthaline
• 522-57-6
• Papaveraldin
• 6,7-Dimethoxy-1-veratroylisoquinoline
• (6,7-Dimethoxy-1-isoquinolyl) (3,4-dimethoxyphenyl) ketone
• (6,7-dimethoxyisoquinolin-1-yl)-(3,4-dimethoxyphenyl)methanone
• Xanthaline;NSC 94266
• UNII-L8825LX0F5
• MLS001360484
• L8825LX0F5
• EINECS 208-331-4
• NSC 94266
• NSC-94266
• SMR001223913
• 6,7-dimethoxy-1-isoquinolyl 3,4-dimethoxyphenyl ketone
• Ketone, 6,7-dimethoxy-1-isoquinolyl 3,4-dimethoxyphenyl
• Methanone, (6,7-dimethoxy-1-isoquinolinyl)(3,4-dimethoxyphenyl)-
• Xanthaline?
• PAPAVERALDINE [MI]
• cid_96932
• SCHEMBL679695
• CHEMBL205040
• BDBM64802
• DTXSID90200239
• CHEBI:174754
• HMS3053F11
• KUC105687N
• NSC94266
• KSC-6-256
• AKOS000277453
• 6, 7-Dimethoxy-1-veratroylisoquinoline
• NCGC00247279-01
• SR-01000855287
• 6,7-Dimethoxy-1-(3,4-dimethoxybenzoyl)isoquinoline
• Q1689762
• SR-01000855287-2
• Ketone,7-dimethoxy-1-isoquinolyl 3,4-dimethoxyphenyl
• (6,7-Dimethoxy-1-isoquinolyl)(3,4-dimethoxyphenyl)ketone
• (6,7-dimethoxy-1-isoquinolyl)-(3,4-dimethoxyphenyl)methanone
• (6,7-dimethoxyisoquinolin-1-yl)(3,4-dimethoxyphenyl)methanone
• 1-[(3,4-dimethoxyphenyl)carbonyl]-6,7-dimethoxyisoquinoline
• Methanone,7-dimethoxy-1-isoquinolinyl)(3,4-dimethoxyphenyl)-
• (6,7-Dimethoxy-1-iso-quinolinyl)(3,4-dimethoxyphenyl)methanone
• (6,7-dimethoxy-1-isoquinolinyl)-(3,4-dimethoxyphenyl)methanone
• (6,7-DIMETHOXY-1-ISOQUINOLINYL)(3,4-DIMETHOXYPHENYL)METHANONE
• InChI=1/C20H19NO5/c1-23-15-6-5-13(10-16(15)24-2)20(22)19-14-11-18(26-4)17(25-3)9-12(14)7-8-21-19/h5-11H,1-4H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9925	99.25%
Caco-2	+	0.9151	91.51%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5927	59.27%
OATP2B1 inhibitior	-	0.8657	86.57%
OATP1B1 inhibitior	+	0.9661	96.61%
OATP1B3 inhibitior	+	0.9788	97.88%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6875	68.75%
P-glycoprotein inhibitior	+	0.7111	71.11%
P-glycoprotein substrate	-	0.5843	58.43%
CYP3A4 substrate	-	0.5661	56.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7304	73.04%
CYP3A4 inhibition	+	0.7897	78.97%
CYP2C9 inhibition	-	0.9146	91.46%
CYP2C19 inhibition	+	0.5231	52.31%
CYP2D6 inhibition	-	0.8268	82.68%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	+	0.8874	88.74%
CYP inhibitory promiscuity	+	0.7384	73.84%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9610	96.10%
Carcinogenicity (trinary)	Non-required	0.6235	62.35%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.7994	79.94%
Skin irritation	-	0.8235	82.35%
Skin corrosion	-	0.9833	98.33%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6606	66.06%
Micronuclear	+	0.6759	67.59%
Hepatotoxicity	+	0.6532	65.32%
skin sensitisation	-	0.9563	95.63%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7771	77.71%
Acute Oral Toxicity (c)	II	0.4618	46.18%
Estrogen receptor binding	+	0.9351	93.51%
Androgen receptor binding	+	0.6779	67.79%
Thyroid receptor binding	+	0.7995	79.95%
Glucocorticoid receptor binding	+	0.8595	85.95%
Aromatase binding	+	0.6032	60.32%
PPAR gamma	+	0.6640	66.40%
Honey bee toxicity	-	0.9561	95.61%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5715	57.15%
Fish aquatic toxicity	-	0.4891	48.91%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1795093	O14727	Apoptotic protease-activating factor 1	24400 nM	IC50	via CMAUP
CHEMBL2334	P42574	Caspase-3	8210 nM	IC50	via CMAUP
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	39810.7 nM	Potency	via CMAUP
CHEMBL1741215	Q9GZR1	Sentrin-specific protease 6	805 nM; 805 nM	IC50; IC50	via Super-PRED; via CMAUP
CHEMBL1741213	Q9BQF6	Sentrin-specific protease 7	1670 nM	IC50	via CMAUP
CHEMBL1741207	Q96LD8	Sentrin-specific protease 8	2470 nM	IC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2535	P11166	Glucose transporter	94.49%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.31%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.65%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.71%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.81%	92.94%
CHEMBL4208	P20618	Proteasome component C5	90.32%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.02%	96.09%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	87.07%	96.47%
CHEMBL1255126	O15151	Protein Mdm4	85.42%	90.20%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.21%	96.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.97%	96.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.48%	89.62%
CHEMBL1951	P21397	Monoamine oxidase A	83.43%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.45%	85.14%

Plants that contains it

• Aloe microstigma
• Chrozophora plicata
• Papaver somniferum
• Vicia faba

Cross-Links

• PubChem: 96932
• NPASS: NPC146976
• ChEMBL: CHEMBL205040
• LOTUS: LTS0037680
• wikiData: Q1689762