Erysodine

Details

• Internal ID: b9a8fae3-6496-4ed9-bf48-64e18be63a78
• Taxonomy: Alkaloids and derivatives > Erythrina alkaloids > Erythrinanes
• IUPAC Name: (2R,13bS)-2,12-dimethoxy-2,6,8,9-tetrahydro-1H-indolo[7a,1-a]isoquinolin-11-ol
• SMILES (Canonical): COC1CC23C(=CCN2CCC4=CC(=C(C=C34)OC)O)C=C1
• SMILES (Isomeric): CO[C@@H]1C[C@@]23C(=CCN2CCC4=CC(=C(C=C34)OC)O)C=C1
• InChI: InChI=1S/C18H21NO3/c1-21-14-4-3-13-6-8-19-7-5-12-9-16(20)17(22-2)10-15(12)18(13,19)11-14/h3-4,6,9-10,14,20H,5,7-8,11H2,1-2H3/t14-,18-/m0/s1
• InChI Key: BDIVMECULLJBMU-KSSFIOAISA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₁NO₃
• Molecular Weight: 299.40 g/mol
• Exact Mass: 299.15214353 g/mol
• Topological Polar Surface Area (TPSA): 41.90 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• Erysodin
• 7290-03-1
• (+)-erysodine
• 6WZ3T41Y11
• (2R,13bS)-2,12-dimethoxy-2,6,8,9-tetrahydro-1H-indolo[7a,1-a]isoquinolin-11-ol
• 1,2,6,7-Tetradehydro-3,15-dimethoxyerythrinan-16-ol
• UNII-6WZ3T41Y11
• CHEMBL446533
• Erythrinan-16-ol, 1,2,6,7-tetradehydro-3,15-dimethoxy-, (3.beta.)-
• DTXSID20993682
• CHEBI:192381
• BDBM50006647
• Q27265641
• 3,15-Dimethoxy-1,2,6,7-tetradehydroerythrinan-16-ol
• 1,2,6,7-tetradehydro-3beta,15-dimethoxyerythrinan-16-ol
• 3beta,15-dimethoxy-1,2,6,7-tetradehydroerythrinan-16-ol
• (3beta)-1,2,6,7-tetradehydro-3,15-dimethoxyerythrinan-16-ol
• 1,2,6,7-Tetradehydro-3,15-dimethoxy-(3beta)-Erythrinan-16-ol
• Erythrinan-16-ol, 1,2,6,7-tetradehydro-3,15-dimethoxy-, (3beta)-
• (12R,13aS)-2,12-dimethoxy-5H,6H,8H,12H,13H-indolo[7a,1-a]isoquinolin-3-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9885	98.85%
Caco-2	+	0.8863	88.63%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8009	80.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9202	92.02%
OATP1B3 inhibitior	+	0.9528	95.28%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	+	0.7350	73.50%
P-glycoprotein inhibitior	-	0.8210	82.10%
P-glycoprotein substrate	-	0.5223	52.23%
CYP3A4 substrate	+	0.6149	61.49%
CYP2C9 substrate	+	0.5764	57.64%
CYP2D6 substrate	+	0.6146	61.46%
CYP3A4 inhibition	-	0.8892	88.92%
CYP2C9 inhibition	-	0.8703	87.03%
CYP2C19 inhibition	-	0.7570	75.70%
CYP2D6 inhibition	+	0.7427	74.27%
CYP1A2 inhibition	-	0.6650	66.50%
CYP2C8 inhibition	-	0.6915	69.15%
CYP inhibitory promiscuity	-	0.7455	74.55%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5865	58.65%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9098	90.98%
Skin irritation	-	0.7520	75.20%
Skin corrosion	-	0.9292	92.92%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3880	38.80%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8299	82.99%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8117	81.17%
Acute Oral Toxicity (c)	III	0.4758	47.58%
Estrogen receptor binding	+	0.8113	81.13%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.6790	67.90%
Glucocorticoid receptor binding	+	0.6776	67.76%
Aromatase binding	+	0.5754	57.54%
PPAR gamma	-	0.5429	54.29%
Honey bee toxicity	-	0.8397	83.97%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5751	57.51%
Fish aquatic toxicity	+	0.7912	79.12%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1907589	P17787	Neuronal acetylcholine receptor; alpha4/beta2	50 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	98.99%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	96.38%	92.94%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.22%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.20%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.02%	85.14%
CHEMBL4208	P20618	Proteasome component C5	89.58%	90.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	89.37%	91.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.35%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.47%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.65%	94.00%
CHEMBL217	P14416	Dopamine D2 receptor	85.80%	95.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.29%	86.33%
CHEMBL2581	P07339	Cathepsin D	85.25%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.74%	89.62%
CHEMBL2535	P11166	Glucose transporter	83.13%	98.75%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.08%	93.40%
CHEMBL2056	P21728	Dopamine D1 receptor	81.87%	91.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.40%	91.07%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	80.16%	96.25%

Plants that contains it

• Erythrina abyssinica
• Erythrina americana
• Erythrina berteroana
• Erythrina bidwillii
• Erythrina brucei
• Erythrina cochleata
• Erythrina crista-galli
• Erythrina latissima
• Erythrina leptorhiza
• Erythrina lysistemon
• Erythrina poeppigiana
• Erythrina senegalensis
• Erythrina smithiana
• Erythrina speciosa
• Erythrina stricta
• Erythrina suberosa
• Erythrina variegata
• Erythrina velutina

Cross-Links

• PubChem: 169017
• LOTUS: LTS0200261
• wikiData: Q27265641