Laudanosine

Details

• Internal ID: b0da9926-2e77-442c-9ae5-1467744d200e
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Benzylisoquinolines
• IUPAC Name: 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
• SMILES (Canonical): CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)OC)OC)OC
• SMILES (Isomeric): CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)OC)OC)OC
• InChI: InChI=1S/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3
• InChI Key: KGPAYJZAMGEDIQ-UHFFFAOYSA-N
• Popularity: 164 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₇NO₄
• Molecular Weight: 357.40 g/mol
• Exact Mass: 357.19400834 g/mol
• Topological Polar Surface Area (TPSA): 40.20 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.49
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• DL-Laudanosine
• 1699-51-0
• (+-)-Laudanosine
• 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
• (R,S)-Laudanosine
• Laudanosine (R,S)
• EINECS 216-923-9
• NSC 94267
• 5',8-Dimethoxylaudanosine hydrochloride
• 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
• AI3-61890
• 20412-65-1
• C21H27NO4
• NSC35045
• 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
• (+-)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinoline
• ISOQUINOLINE, 1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2-METHYL-1-VERATRYL-, (+-)-
• (1)-1-((3,4-Dimethoxyphenyl)methyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline
• Isoquinoline, 1-((3,4-dimethoxyphenyl)methyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (+-)-
• Isoquinoline,1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (1R)-
• SMR000064381
• Veraisoquin
• dl-Laudanosin
• NSC-35045
• Prestwick_292
• Spectrum_000863
• (.+-.)-Laudanosine
• SpecPlus_000088
• Prestwick0_000591
• Prestwick1_000591
• Prestwick2_000591
• Prestwick3_000591
• Spectrum2_000663
• Spectrum3_000112
• Spectrum4_000934
• Spectrum5_001625
• (.+/-.)-Laudanosine
• DL-Laudanosine, free base
• D01VUF
• D0F7FX
• CHEMBL1407
• Oprea1_379167
• BSPBio_000462
• BSPBio_001724
• KBioGR_001488
• KBioSS_001343
• MLS000060551
• MLS002634637
• DivK1c_006184
• SCHEMBL466529
• SPBio_000725
• SPBio_002681
• BPBio1_000510
• CHEBI:91599
• KBio1_001128
• KBio2_001343
• KBio2_003911
• KBio2_006479
• KBio3_000864
• DTXSID00871873
• KGPAYJZAMGEDIQ-UHFFFAOYSA-N
• HMS1569H04
• HMS2096H04
• HMS2271K11
• EX-A3381
• NSC94267
• BDBM50270376
• CCG-38566
• MFCD00006910
• NSC-94267
• NSC331268
• STL570293
• 3-CYCLOHEX-1-ENYL-ACRYLICACID
• AKOS001094404
• AKOS022144164
• NSC-331268
• 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoqu inoline
• isoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-
• NCGC00017301-02
• NCGC00142367-01
• AS-37336
• LS-85945
• HY-122489
• AB00052572
• CS-0085743
• FT-0625478
• FT-0670745
• EN300-180011
• L-1400
• AB00052572-12
• A900016
• A937069
• BRD-A24817035-001-05-4
• Q27163429
• Z57474215
• Isoquinoline,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratryl-
• Isoquinoline, 1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratryl-
• (.+/-.)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinoline
• (R)-1-(3',4'-dimethoxybenzyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• Isoquinoline, 1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratryl-, (.+.)-
• Isoquinoline, 1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratryl-, (.+/-.)-
• Isoquinoline,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratryl-, (.+-.)-
• Isoquinoline,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-
• (+-)-1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline
• Isoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (.+.)-
• Isoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (.+/-.)-
• Isoquinoline,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (.+-.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9591	95.91%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5912	59.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9533	95.33%
OATP1B3 inhibitior	+	0.9492	94.92%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.7897	78.97%
P-glycoprotein inhibitior	+	0.9145	91.45%
P-glycoprotein substrate	+	0.6233	62.33%
CYP3A4 substrate	+	0.6191	61.91%
CYP2C9 substrate	+	0.7753	77.53%
CYP2D6 substrate	+	0.8760	87.60%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	-	0.6068	60.68%
CYP2C8 inhibition	-	0.6862	68.62%
CYP inhibitory promiscuity	-	0.8451	84.51%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6948	69.48%
Eye corrosion	-	0.9941	99.41%
Eye irritation	-	0.9709	97.09%
Skin irritation	-	0.7758	77.58%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9224	92.24%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9050	90.50%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.8773	87.73%
Acute Oral Toxicity (c)	III	0.8081	80.81%
Estrogen receptor binding	+	0.7009	70.09%
Androgen receptor binding	-	0.7275	72.75%
Thyroid receptor binding	+	0.6552	65.52%
Glucocorticoid receptor binding	+	0.6247	62.47%
Aromatase binding	-	0.6524	65.24%
PPAR gamma	-	0.5540	55.40%
Honey bee toxicity	-	0.8781	87.81%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9033	90.33%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	25118.9 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	10000 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	17.8 nM; 316.2 nM; 17.8 nM	Potency; Potency; Potency	via Super-PRED; via Super-PRED; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.08%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.78%	85.14%
CHEMBL2581	P07339	Cathepsin D	95.04%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.19%	95.89%
CHEMBL5747	Q92793	CREB-binding protein	92.36%	95.12%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.26%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.42%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.27%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.26%	86.33%
CHEMBL2535	P11166	Glucose transporter	88.07%	98.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.56%	97.25%
CHEMBL261	P00915	Carbonic anhydrase I	87.16%	96.76%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.63%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.54%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.17%	95.56%
CHEMBL4208	P20618	Proteasome component C5	84.07%	90.00%
CHEMBL5555	O00767	Acyl-CoA desaturase	82.38%	97.50%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	81.81%	90.95%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.74%	89.50%
CHEMBL3474	P14555	Phospholipase A2 group IIA	81.69%	94.05%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.70%	92.62%

Plants that contains it

• Berberis heteropoda
• Berberis nummularia
• Cissampelos pareira
• Guatteria amplifolia
• Papaver macrostomum
• Papaver somniferum
• Papaver somniferum subsp. setigerum

Cross-Links

• PubChem: 15548
• NPASS: NPC328750
• ChEMBL: CHEMBL1407
• LOTUS: LTS0094818
• wikiData: Q27163429