Macrostomine

Details

• Internal ID: d08740e8-b250-455d-8ad4-0d39262e4323
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > Pyrrolidinylpyridines
• IUPAC Name: 1-(1,3-benzodioxol-5-ylmethyl)-6,7-dimethoxy-4-[(2S)-1-methylpyrrolidin-2-yl]isoquinoline
• SMILES (Canonical): CN1CCCC1C2=CN=C(C3=CC(=C(C=C32)OC)OC)CC4=CC5=C(C=C4)OCO5
• SMILES (Isomeric): CN1CCC[C@H]1C2=CN=C(C3=CC(=C(C=C32)OC)OC)CC4=CC5=C(C=C4)OCO5
• InChI: InChI=1S/C24H26N2O4/c1-26-8-4-5-20(26)18-13-25-19(9-15-6-7-21-24(10-15)30-14-29-21)17-12-23(28-3)22(27-2)11-16(17)18/h6-7,10-13,20H,4-5,8-9,14H2,1-3H3/t20-/m0/s1
• InChI Key: XISGRFQSYRKPNQ-FQEVSTJZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₆N₂O₄
• Molecular Weight: 406.50 g/mol
• Exact Mass: 406.18925731 g/mol
• Topological Polar Surface Area (TPSA): 53.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.34
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• 53912-94-0
• (S)-Macrostomine
• DTXSID10202194
• Isoquinoline, 1-(1,3-benzodioxol-5-ylmethyl)-6,7-dimethoxy-4-(1-methyl-2-pyrrolidinyl)-, (S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9397	93.97%
Caco-2	+	0.7764	77.64%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.3741	37.41%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	+	0.9000	90.00%
OATP1B3 inhibitior	+	0.9349	93.49%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9720	97.20%
P-glycoprotein inhibitior	+	0.9379	93.79%
P-glycoprotein substrate	+	0.6985	69.85%
CYP3A4 substrate	+	0.6508	65.08%
CYP2C9 substrate	-	0.6044	60.44%
CYP2D6 substrate	+	0.6315	63.15%
CYP3A4 inhibition	+	0.8785	87.85%
CYP2C9 inhibition	-	0.6221	62.21%
CYP2C19 inhibition	-	0.5913	59.13%
CYP2D6 inhibition	-	0.5352	53.52%
CYP1A2 inhibition	-	0.6488	64.88%
CYP2C8 inhibition	-	0.5718	57.18%
CYP inhibitory promiscuity	+	0.9064	90.64%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5852	58.52%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9838	98.38%
Skin irritation	-	0.8000	80.00%
Skin corrosion	-	0.9468	94.68%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8716	87.16%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.8867	88.67%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.9153	91.53%
Acute Oral Toxicity (c)	III	0.7421	74.21%
Estrogen receptor binding	+	0.7268	72.68%
Androgen receptor binding	+	0.6305	63.05%
Thyroid receptor binding	+	0.7310	73.10%
Glucocorticoid receptor binding	+	0.8428	84.28%
Aromatase binding	+	0.6473	64.73%
PPAR gamma	+	0.7349	73.49%
Honey bee toxicity	-	0.7078	70.78%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.9034	90.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.36%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.15%	96.09%
CHEMBL5203	P33316	dUTP pyrophosphatase	97.80%	99.18%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.12%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	96.51%	95.89%
CHEMBL5747	Q92793	CREB-binding protein	95.94%	95.12%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	94.85%	92.62%
CHEMBL235	P37231	Peroxisome proliferator-activated receptor gamma	94.46%	95.39%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.30%	85.14%
CHEMBL2581	P07339	Cathepsin D	93.30%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.74%	94.00%
CHEMBL1741221	Q9Y4P1	Cysteine protease ATG4B	92.50%	87.50%
CHEMBL2535	P11166	Glucose transporter	91.71%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.68%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.44%	86.33%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	90.11%	91.43%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.33%	95.78%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.32%	94.80%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.51%	93.40%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	85.79%	96.69%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.72%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.55%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.32%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.25%	92.94%
CHEMBL239	Q07869	Peroxisome proliferator-activated receptor alpha	84.79%	90.75%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	84.52%	85.83%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.51%	82.67%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	84.12%	90.95%
CHEMBL4208	P20618	Proteasome component C5	82.79%	90.00%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	82.47%	92.38%
CHEMBL1827	O76074	Phosphodiesterase 5A	81.01%	99.55%
CHEMBL240	Q12809	HERG	80.93%	89.76%
CHEMBL261	P00915	Carbonic anhydrase I	80.86%	96.76%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.68%	82.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.43%	89.00%
CHEMBL5406	Q86X55	Histone-arginine methyltransferase CARM1	80.42%	94.33%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.13%	92.38%

Plants that contains it

• Papaver arenarium
• Papaver macrostomum

Cross-Links

• PubChem: 185760
• LOTUS: LTS0237874
• wikiData: Q83075467