Corypalmine

Details

• Internal ID: e296430b-3b3c-4ec4-82c8-24afb371c388
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: 2,9,10-trimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-3-ol
• SMILES (Canonical): COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)O)OC)C=C1)OC
• SMILES (Isomeric): COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)O)OC)C=C1)OC
• InChI: InChI=1S/C20H23NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,9-10,16,22H,6-8,11H2,1-3H3
• InChI Key: BMCZTYDZHNTKPR-UHFFFAOYSA-N
• Popularity: 21 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): 51.20 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.07
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• Corypalmine
• 27313-86-6
• dl-Corypalmine
• (R)-(+)-Corypalmine
• 13063-54-2
• Tetrahydrojatrorrhizine
• dl-Tetrahydrojatrorrhizine
• Corypalmine, (+/-)-
• Discretinine
• 2,9,10-trimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-3-ol
• 2,9,10-trimethoxyberbin-3-ol
• 60ZPV7979L
• Tetrahydrojateorrhizine
• 6018-40-2
• 6H-Dibenzo(a,g)quinolizin-3-ol, 5,8,13,13a-tetrahydro-2,9,10-trimethoxy-
• ( inverted exclamation markA)-Corypalmine
• NoName_4241
• (+/-)-DISCRETININE
• SCHEMBL231003
• Corypalmin; Corypalmine; Corypalmine, (-)-; l-Tetrahydrojatrorrhizine
• CORYPALMINE DL-FORM [MI]
• DTXSID30903555
• BMCZTYDZHNTKPR-UHFFFAOYSA-N
• HY-N0654
• (invertedexclamationmarkA)-Corypalmine
• (+/-)-TETRAHYDROJATRORRHIZINE
• AKOS000277451
• AS-72901
• CS-0009677
• FT-0624069
• FT-0688342
• C74412
• Q27263256
• B0005-129029
• 3,4,11-trimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphen-10-ol
• 2,9,10-Trimethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinolin-3-ol #
• 5,8,13,13A-TETRAHYDRO-2,9,10-TRIMETHOXY-6H-DIBENZO(A,G)QUINOLIZIN-3-OL
• Isoquino[2,1-b]isoquinoline, 4b,5,10,10a,11,12-hexahydro-2-hydroxy-3,8,9-tris(methoxy)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7960	79.60%
Caco-2	+	0.8955	89.55%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7489	74.89%
OATP2B1 inhibitior	-	0.8590	85.90%
OATP1B1 inhibitior	+	0.9430	94.30%
OATP1B3 inhibitior	+	0.9426	94.26%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	+	0.6500	65.00%
BSEP inhibitior	-	0.5191	51.91%
P-glycoprotein inhibitior	-	0.5857	58.57%
P-glycoprotein substrate	-	0.5726	57.26%
CYP3A4 substrate	+	0.5974	59.74%
CYP2C9 substrate	+	0.7825	78.25%
CYP2D6 substrate	+	0.8432	84.32%
CYP3A4 inhibition	-	0.7612	76.12%
CYP2C9 inhibition	-	0.9271	92.71%
CYP2C19 inhibition	-	0.5838	58.38%
CYP2D6 inhibition	+	0.7241	72.41%
CYP1A2 inhibition	+	0.6514	65.14%
CYP2C8 inhibition	-	0.5587	55.87%
CYP inhibitory promiscuity	-	0.8609	86.09%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6527	65.27%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9031	90.31%
Skin irritation	-	0.7540	75.40%
Skin corrosion	-	0.9415	94.15%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6866	68.66%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8969	89.69%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.7459	74.59%
Acute Oral Toxicity (c)	III	0.4821	48.21%
Estrogen receptor binding	+	0.6737	67.37%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.6482	64.82%
Glucocorticoid receptor binding	+	0.6318	63.18%
Aromatase binding	-	0.7406	74.06%
PPAR gamma	-	0.6154	61.54%
Honey bee toxicity	-	0.8955	89.55%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.6151	61.51%
Fish aquatic toxicity	-	0.4210	42.10%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2056	P21728	Dopamine D1 receptor	199 nM	Ki	via Super-PRED
CHEMBL217	P14416	Dopamine D2 receptor	42.4 nM	Ki	via Super-PRED
CHEMBL234	P35462	Dopamine D3 receptor	262 nM	Ki	via Super-PRED
CHEMBL1850	P21918	Dopamine D5 receptor	313 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.77%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.28%	93.40%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.07%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.07%	86.33%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	91.62%	91.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.52%	94.45%
CHEMBL2535	P11166	Glucose transporter	91.38%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.58%	89.62%
CHEMBL5747	Q92793	CREB-binding protein	89.23%	95.12%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.13%	95.56%
CHEMBL3438	Q05513	Protein kinase C zeta	89.11%	88.48%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.70%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.98%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.03%	85.14%
CHEMBL2581	P07339	Cathepsin D	85.75%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.62%	95.89%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	85.17%	82.38%
CHEMBL4208	P20618	Proteasome component C5	84.44%	90.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.03%	93.99%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.77%	99.17%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.30%	100.00%
CHEMBL4302	P08183	P-glycoprotein 1	81.24%	92.98%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.22%	91.03%

Plants that contains it

• Annona leptopetala
• Argemone grandiflora
• Corydalis chaerophylla
• Corydalis heterocarpa
• Corydalis nobilis
• Corydalis solida
• Corydalis ternata
• Corydalis turtschaninovii
• Corydalis yanhusuo
• Fibraurea recisa
• Glaucium grandiflorum
• Guatteria friesiana
• Magnolia compressa
• Phellodendron amurense
• Phellodendron chinense
• Pseudofumaria lutea
• Xylopia discreta

Cross-Links

• PubChem: 185605
• NPASS: NPC138488
• LOTUS: LTS0265353
• wikiData: Q27263256