Lotusine

Details

• Internal ID: de64654a-7c8f-473d-8ba6-edfeacb140e4
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Benzylisoquinolines
• IUPAC Name: (1R)-1-[(4-hydroxyphenyl)methyl]-7-methoxy-2,2-dimethyl-3,4-dihydro-1H-isoquinolin-2-ium-6-ol
• SMILES (Canonical): C[N+]1(CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)O)OC)O)C
• SMILES (Isomeric): C[N+]1(CCC2=CC(=C(C=C2[C@H]1CC3=CC=C(C=C3)O)OC)O)C
• InChI: InChI=1S/C19H23NO3/c1-20(2)9-8-14-11-18(22)19(23-3)12-16(14)17(20)10-13-4-6-15(21)7-5-13/h4-7,11-12,17H,8-10H2,1-3H3,(H-,21,22)/p+1/t17-/m1/s1
• InChI Key: ZKTMLINFIQCERN-QGZVFWFLSA-O
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄NO₃+
• Molecular Weight: 314.40 g/mol
• Exact Mass: 314.17561863 g/mol
• Topological Polar Surface Area (TPSA): 49.70 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.02
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 6871-67-6
• (1R)-1,2,3,4-Tetrahydro-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-7-methoxy-2,2-dimethylisoquinolinium
• (-)-Lotusine
• (1R)-1-[(4-hydroxyphenyl)methyl]-7-methoxy-2,2-dimethyl-3,4-dihydro-1H-isoquinolin-2-ium-6-ol
• D-(-)-Lotusine
• CHEBI:81190
• DTXSID501317849
• HY-N4309
• AKOS037515015
• AC-34435
• CS-0032713
• C17567
• E80653
• Q27155136
• (1R)-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydroisoquinolin-2-ium
• Isoquinolinium, 1,2,3,4-tetrahydro-6-hydroxy-1-[(4-hydroxyphenyl)methyl]-7-methoxy-2,2-dimethyl-, (1R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9501	95.01%
Caco-2	+	0.8564	85.64%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6564	65.64%
OATP2B1 inhibitior	-	0.8418	84.18%
OATP1B1 inhibitior	+	0.9339	93.39%
OATP1B3 inhibitior	+	0.9447	94.47%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.6704	67.04%
P-glycoprotein substrate	-	0.6544	65.44%
CYP3A4 substrate	+	0.5976	59.76%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	+	0.5000	50.00%
CYP3A4 inhibition	-	0.9635	96.35%
CYP2C9 inhibition	-	0.8981	89.81%
CYP2C19 inhibition	-	0.8781	87.81%
CYP2D6 inhibition	-	0.5245	52.45%
CYP1A2 inhibition	-	0.7361	73.61%
CYP2C8 inhibition	+	0.8607	86.07%
CYP inhibitory promiscuity	-	0.9126	91.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7175	71.75%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.8684	86.84%
Skin irritation	-	0.7783	77.83%
Skin corrosion	-	0.9214	92.14%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8683	86.83%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8694	86.94%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.9407	94.07%
Acute Oral Toxicity (c)	III	0.6358	63.58%
Estrogen receptor binding	+	0.6218	62.18%
Androgen receptor binding	+	0.5643	56.43%
Thyroid receptor binding	+	0.7698	76.98%
Glucocorticoid receptor binding	+	0.6604	66.04%
Aromatase binding	+	0.6626	66.26%
PPAR gamma	+	0.7644	76.44%
Honey bee toxicity	-	0.8535	85.35%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6151	61.51%
Fish aquatic toxicity	+	0.9204	92.04%

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	98.89%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.51%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.89%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.44%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.18%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.67%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.66%	95.89%
CHEMBL2535	P11166	Glucose transporter	90.70%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.94%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.88%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.23%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.94%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.68%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.63%	94.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	85.69%	93.10%
CHEMBL5896	O75164	Lysine-specific demethylase 4A	83.72%	99.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.13%	92.62%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.20%	89.62%
CHEMBL4208	P20618	Proteasome component C5	81.96%	90.00%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	81.84%	89.44%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.59%	91.71%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	81.26%	96.69%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	80.86%	91.79%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	80.52%	85.49%

Plants that contains it

• Linum usitatissimum
• Magnolia obovata
• Magnolia officinalis
• Nelumbo nucifera
• Phellodendron amurense
• Phellodendron chinense
• Xylopia parviflora

Cross-Links

• PubChem: 5274587
• NPASS: NPC132097
• LOTUS: LTS0050545
• wikiData: Q27155136