(2R,9R,13bS)-2,11,12-trimethoxy-7-oxido-2,6,8,9-tetrahydro-1H-indolo[7a,1-a]isoquinolin-7-ium-9-ol

Details

• Internal ID: 39dba5ec-2c6a-44f1-8906-3f464dfb092a
• Taxonomy: Alkaloids and derivatives > Erythrina alkaloids > Erythrinanes
• IUPAC Name: (2R,9R,13bS)-2,11,12-trimethoxy-7-oxido-2,6,8,9-tetrahydro-1H-indolo[7a,1-a]isoquinolin-7-ium-9-ol
• SMILES (Canonical): COC1CC23C(=CC[N+]2(CC(C4=CC(=C(C=C34)OC)OC)O)[O-])C=C1
• SMILES (Isomeric): CO[C@@H]1C[C@@]23C(=CC[N+]2(C[C@@H](C4=CC(=C(C=C34)OC)OC)O)[O-])C=C1
• InChI: InChI=1S/C19H23NO5/c1-23-13-5-4-12-6-7-20(22)11-16(21)14-8-17(24-2)18(25-3)9-15(14)19(12,20)10-13/h4-6,8-9,13,16,21H,7,10-11H2,1-3H3/t13-,16-,19-,20?/m0/s1
• InChI Key: DWXDTNCZRDEMJI-YNCSRZAISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₃NO₅
• Molecular Weight: 345.40 g/mol
• Exact Mass: 345.15762283 g/mol
• Topological Polar Surface Area (TPSA): 66.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 2.18
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7027	70.27%
Caco-2	+	0.7263	72.63%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4099	40.99%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.8923	89.23%
OATP1B3 inhibitior	+	0.9411	94.11%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.6319	63.19%
P-glycoprotein inhibitior	-	0.7001	70.01%
P-glycoprotein substrate	-	0.5426	54.26%
CYP3A4 substrate	+	0.6177	61.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7426	74.26%
CYP3A4 inhibition	-	0.9011	90.11%
CYP2C9 inhibition	-	0.8118	81.18%
CYP2C19 inhibition	-	0.7089	70.89%
CYP2D6 inhibition	-	0.7665	76.65%
CYP1A2 inhibition	-	0.7983	79.83%
CYP2C8 inhibition	+	0.5555	55.55%
CYP inhibitory promiscuity	-	0.9109	91.09%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.4402	44.02%
Eye corrosion	-	0.9803	98.03%
Eye irritation	-	0.9012	90.12%
Skin irritation	-	0.7613	76.13%
Skin corrosion	-	0.9209	92.09%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4160	41.60%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8234	82.34%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.7765	77.65%
Acute Oral Toxicity (c)	III	0.5680	56.80%
Estrogen receptor binding	+	0.7871	78.71%
Androgen receptor binding	+	0.5843	58.43%
Thyroid receptor binding	+	0.8124	81.24%
Glucocorticoid receptor binding	+	0.6467	64.67%
Aromatase binding	+	0.5509	55.09%
PPAR gamma	-	0.6098	60.98%
Honey bee toxicity	-	0.8292	82.92%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5249	52.49%
Fish aquatic toxicity	+	0.8462	84.62%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.19%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.99%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.86%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.14%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.84%	86.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.82%	89.62%
CHEMBL4208	P20618	Proteasome component C5	84.16%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.96%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.54%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.51%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.55%	95.56%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.15%	91.03%

Plants that contains it

• Erythrina americana

Cross-Links

• PubChem: 11152146
• LOTUS: LTS0010021
• wikiData: Q104375888