(S)-Laudanine

Details

• Internal ID: 9aed55fd-e9a9-4848-96f7-9698bc923b48
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Benzylisoquinolines
• IUPAC Name: 5-[[(1S)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-2-methoxyphenol
• SMILES (Canonical): CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)O)OC)OC
• SMILES (Isomeric): CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)O)OC)OC
• InChI: InChI=1S/C20H25NO4/c1-21-8-7-14-11-19(24-3)20(25-4)12-15(14)16(21)9-13-5-6-18(23-2)17(22)10-13/h5-6,10-12,16,22H,7-9H2,1-4H3/t16-/m0/s1
• InChI Key: MPYHGNAJOKCMAQ-INIZCTEOSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₅NO₄
• Molecular Weight: 343.40 g/mol
• Exact Mass: 343.17835828 g/mol
• Topological Polar Surface Area (TPSA): 51.20 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• L-(+)-Laudanidine
• (+)-Laudanidine
• 3122-95-0
• Laudanine, (+)-
• 1alphaH-Laudanidine
• (+)-laudanine
• UNII-347215J9V9
• 5-[[(1S)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-2-methoxyphenol
• 347215J9V9
• CHEBI:76101
• Phenol, 2-methoxy-5-(((1S)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)-
• 5-[((1S)-6,7-Dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-2-methoxyphenol
• 5-{[(1S)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}-2-methoxyphenol
• 1.ALPHA.H-LAUDANIDINE
• CHEMBL251625
• SCHEMBL15696580
• DTXSID10356308
• MPYHGNAJOKCMAQ-INIZCTEOSA-N
• Phenol, 2-methoxy-5-[(1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl]-, (S)-
• C20712
• Q27145751
• 2-Methoxy-5-[[(1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinolin)-1alpha-yl]methyl]phenol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8515	85.15%
Caco-2	+	0.8685	86.85%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6573	65.73%
OATP2B1 inhibitior	-	0.8629	86.29%
OATP1B1 inhibitior	+	0.9445	94.45%
OATP1B3 inhibitior	+	0.9432	94.32%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.6940	69.40%
P-glycoprotein inhibitior	+	0.7461	74.61%
P-glycoprotein substrate	+	0.5596	55.96%
CYP3A4 substrate	+	0.6385	63.85%
CYP2C9 substrate	+	0.7825	78.25%
CYP2D6 substrate	+	0.8432	84.32%
CYP3A4 inhibition	-	0.8775	87.75%
CYP2C9 inhibition	-	0.9063	90.63%
CYP2C19 inhibition	-	0.9287	92.87%
CYP2D6 inhibition	+	0.8221	82.21%
CYP1A2 inhibition	+	0.7390	73.90%
CYP2C8 inhibition	-	0.5713	57.13%
CYP inhibitory promiscuity	-	0.8980	89.80%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7249	72.49%
Eye corrosion	-	0.9937	99.37%
Eye irritation	-	0.9793	97.93%
Skin irritation	-	0.7627	76.27%
Skin corrosion	-	0.9341	93.41%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8600	86.00%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.9009	90.09%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8863	88.63%
Acute Oral Toxicity (c)	III	0.7877	78.77%
Estrogen receptor binding	+	0.6143	61.43%
Androgen receptor binding	-	0.7371	73.71%
Thyroid receptor binding	+	0.6563	65.63%
Glucocorticoid receptor binding	+	0.6359	63.59%
Aromatase binding	-	0.5541	55.41%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8889	88.89%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.8879	88.79%

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	99.31%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.70%	85.14%
CHEMBL2581	P07339	Cathepsin D	95.74%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.36%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.82%	95.89%
CHEMBL261	P00915	Carbonic anhydrase I	91.75%	96.76%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.56%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.33%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	91.18%	91.49%
CHEMBL2535	P11166	Glucose transporter	89.58%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.00%	94.00%
CHEMBL4208	P20618	Proteasome component C5	88.54%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.93%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.39%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.32%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.61%	93.40%
CHEMBL217	P14416	Dopamine D2 receptor	84.33%	95.62%
CHEMBL5747	Q92793	CREB-binding protein	84.22%	95.12%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.93%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.65%	99.17%
CHEMBL2056	P21728	Dopamine D1 receptor	82.65%	91.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.65%	91.11%

Plants that contains it

• Aglaia odorata
• Aloe microstigma
• Chrozophora plicata
• Croton celtidifolius
• Cryptocarya amygdalina
• Euphorbia lathyris
• Papaver somniferum
• Phoenix dactylifera
• Solanum lasiocarpum
• Stephania cephalantha
• Stephania viridiflavens
• Xylopia parviflora

Cross-Links

• PubChem: 821396
• NPASS: NPC24233
• LOTUS: LTS0153755
• wikiData: Q27145751