8,9-Dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline

Details

• Internal ID: a92203b5-e3ec-4b19-8f1f-4478c4322f4e
• Taxonomy: Organoheterocyclic compounds > Tetrahydroisoquinolines
• IUPAC Name: 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline
• SMILES (Canonical): COC1=C(C=C2C3CCCN3CCC2=C1)OC
• SMILES (Isomeric): COC1=C(C=C2C3CCCN3CCC2=C1)OC
• InChI: InChI=1S/C14H19NO2/c1-16-13-8-10-5-7-15-6-3-4-12(15)11(10)9-14(13)17-2/h8-9,12H,3-7H2,1-2H3
• InChI Key: MVIOZTSBCZNBFR-UHFFFAOYSA-N
• Popularity: 21 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₉NO₂
• Molecular Weight: 233.31 g/mol
• Exact Mass: 233.141578849 g/mol
• Topological Polar Surface Area (TPSA): 21.70 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.40
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline
• CHEMBL3235509
• Crispine A
• 1,2,3,5,6,10b-Hexahydro-8,9-dimethoxypyrrolo[2,1-a]isoquinoline
• BDBM50006633
• 8,9-dimethoxy-2,3,4,5,6,10b-hexahydro-1H-pyrrolo[2,1-a]isoquinoline
• InChI=1/C14H19NO2/c1-16-13-8-10-5-7-15-6-3-4-12(15)11(10)9-14(13)17-2/h8-9,12H,3-7H2,1-2H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9953	99.53%
Caco-2	+	0.9423	94.23%
Blood Brain Barrier	+	0.9379	93.79%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7550	75.50%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.9375	93.75%
OATP1B3 inhibitior	+	0.9554	95.54%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.7500	75.00%
BSEP inhibitior	-	0.6902	69.02%
P-glycoprotein inhibitior	-	0.9308	93.08%
P-glycoprotein substrate	-	0.6359	63.59%
CYP3A4 substrate	+	0.5252	52.52%
CYP2C9 substrate	+	0.7753	77.53%
CYP2D6 substrate	+	0.8760	87.60%
CYP3A4 inhibition	-	0.6668	66.68%
CYP2C9 inhibition	-	0.8111	81.11%
CYP2C19 inhibition	-	0.5232	52.32%
CYP2D6 inhibition	+	0.9232	92.32%
CYP1A2 inhibition	+	0.6640	66.40%
CYP2C8 inhibition	-	0.8720	87.20%
CYP inhibitory promiscuity	+	0.6429	64.29%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6055	60.55%
Eye corrosion	-	0.9799	97.99%
Eye irritation	-	0.8339	83.39%
Skin irritation	-	0.7110	71.10%
Skin corrosion	-	0.9066	90.66%
Ames mutagenesis	-	0.8554	85.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7677	76.77%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8604	86.04%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.4724	47.24%
Acute Oral Toxicity (c)	II	0.8121	81.21%
Estrogen receptor binding	-	0.9202	92.02%
Androgen receptor binding	-	0.7532	75.32%
Thyroid receptor binding	-	0.5696	56.96%
Glucocorticoid receptor binding	-	0.5321	53.21%
Aromatase binding	-	0.7097	70.97%
PPAR gamma	-	0.8902	89.02%
Honey bee toxicity	-	0.9249	92.49%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.8148	81.48%
Fish aquatic toxicity	-	0.6165	61.65%

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	95.88%	96.09%
CHEMBL217	P14416	Dopamine D2 receptor	95.00%	95.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.83%	92.94%
CHEMBL2581	P07339	Cathepsin D	92.89%	98.95%
CHEMBL5203	P33316	dUTP pyrophosphatase	92.08%	99.18%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.77%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.16%	89.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.01%	85.14%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	87.86%	90.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.80%	86.33%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	86.49%	91.43%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.57%	95.56%
CHEMBL5747	Q92793	CREB-binding protein	85.10%	95.12%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.50%	93.99%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	84.47%	96.86%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.99%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.91%	97.14%
CHEMBL2056	P21728	Dopamine D1 receptor	82.48%	91.00%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	82.04%	94.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.65%	94.45%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	81.41%	82.67%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.34%	91.03%
CHEMBL2535	P11166	Glucose transporter	81.20%	98.75%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.13%	93.40%
CHEMBL284	P27487	Dipeptidyl peptidase IV	80.77%	95.69%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.49%	97.25%
CHEMBL6031	Q9H9B1	Histone-lysine N-methyltransferase, H3 lysine-9 specific 5	80.32%	94.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.09%	97.09%

Plants that contains it

• Carduus crispus

Cross-Links

• PubChem: 10263398
• LOTUS: LTS0052615
• wikiData: Q105173048