1,10-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol

Details

• Internal ID: 39afa21d-0589-43f9-8b25-81e6a80caa77
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: 1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
• SMILES (Canonical): CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)O)OC)O
• SMILES (Isomeric): CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)O)OC)O
• InChI: InChI=1S/C19H21NO4/c1-20-5-4-10-7-15(22)19(24-3)18-12-9-16(23-2)14(21)8-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3
• InChI Key: LZJRNLRASBVRRX-UHFFFAOYSA-N
• Popularity: 19 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.40 g/mol
• Exact Mass: 327.14705815 g/mol
• Topological Polar Surface Area (TPSA): 62.20 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.87
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• NSC65689
• MLS000736729
• Boldine--chloroform
• 55056-93-4
• SMR000440559
• (+)-(S)-Boldine
• SR-01000758928
• NSC-65689
• Spectrum_001124
• SpecPlus_000519
• Prestwick0_000600
• Prestwick1_000600
• Prestwick2_000600
• Spectrum2_000595
• Spectrum3_000719
• Spectrum4_001888
• Spectrum5_000516
• D0LH4L
• Oprea1_772115
• BSPBio_002537
• KBioGR_002420
• KBioSS_001604
• MLS000876773
• DivK1c_006615
• SCHEMBL177549
• SPECTRUM1500862
• SPBio_000470
• SPBio_002699
• MEGxp0_001692
• CHEMBL1321247
• ACon1_002196
• CHEBI:95169
• KBio1_001559
• KBio2_001604
• KBio2_004172
• KBio2_006740
• KBio3_001757
• DTXSID90871665
• 5,6,6a,7-Tetrahydro-1,10-dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline-2,9-diol
• HMS1569H22
• HMS2270O15
• HMS3372F12
• CCG-38516
• STL373090
• AKOS015964955
• SDCCGMLS-0066945.P001
• SMP1_000047
• NCGC00017314-02
• NCGC00017314-03
• NCGC00017314-04
• NCGC00017314-05
• NCGC00095964-01
• NCGC00095964-02
• NCGC00178611-01
• NCGC00178611-02
• NCI60_019674
• 6a.alpha.-Aporphine-2, 1,10-dimethoxy-
• SR-01000758928-5
• SR-01000758928-6
• BRD-A44966919-001-04-9
• BRD-A44966919-001-09-8
• Q27166971
• 4H-Dibenzo[de,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8085	80.85%
Caco-2	+	0.8546	85.46%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5804	58.04%
OATP2B1 inhibitior	-	0.8456	84.56%
OATP1B1 inhibitior	+	0.9300	93.00%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.4562	45.62%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.8070	80.70%
CYP3A4 substrate	+	0.5886	58.86%
CYP2C9 substrate	+	0.7825	78.25%
CYP2D6 substrate	+	0.8432	84.32%
CYP3A4 inhibition	-	0.8593	85.93%
CYP2C9 inhibition	-	0.9081	90.81%
CYP2C19 inhibition	-	0.8384	83.84%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	+	0.9378	93.78%
CYP2C8 inhibition	-	0.7795	77.95%
CYP inhibitory promiscuity	-	0.9213	92.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7029	70.29%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9207	92.07%
Skin irritation	-	0.7540	75.40%
Skin corrosion	-	0.9347	93.47%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4173	41.73%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	-	0.7949	79.49%
skin sensitisation	-	0.8960	89.60%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.8951	89.51%
Acute Oral Toxicity (c)	III	0.7111	71.11%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.5794	57.94%
Thyroid receptor binding	+	0.5941	59.41%
Glucocorticoid receptor binding	+	0.8229	82.29%
Aromatase binding	-	0.5433	54.33%
PPAR gamma	+	0.7521	75.21%
Honey bee toxicity	-	0.8975	89.75%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.8948	89.48%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	28183.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	28183.8 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	25118.9 nM; 25118.9 nM; 25118.9 nM; 25118.9 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM; 31622.8 nM; 31622.8 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	35481.3 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	707.9 nM; 11220.2 nM; 707.9 nM; 707.9 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	316.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.05%	96.09%
CHEMBL217	P14416	Dopamine D2 receptor	98.02%	95.62%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	95.75%	91.79%
CHEMBL2056	P21728	Dopamine D1 receptor	94.88%	91.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.84%	91.11%
CHEMBL3438	Q05513	Protein kinase C zeta	92.82%	88.48%
CHEMBL1951	P21397	Monoamine oxidase A	91.90%	91.49%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	91.17%	91.03%
CHEMBL4208	P20618	Proteasome component C5	90.15%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.00%	95.56%
CHEMBL5747	Q92793	CREB-binding protein	88.83%	95.12%
CHEMBL2581	P07339	Cathepsin D	88.66%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.96%	93.40%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.18%	85.14%
CHEMBL2535	P11166	Glucose transporter	87.11%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.92%	89.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.02%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.56%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.88%	86.33%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	84.80%	82.38%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.77%	93.03%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	83.58%	96.86%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.48%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.16%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.65%	89.00%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	80.06%	95.70%

Plants that contains it

• Actinodaphne pruinosa
• Beilschmiedia alloiophylla
• Beilschmiedia kunstleri
• Hedycarya angustifolia
• Lindera aggregata
• Lindera glauca
• Litsea glutinosa
• Litsea leefeana
• Litsea turfosa
• Litsea wightiana
• Neolitsea acuminatissima
• Neolitsea dealbata
• Neolitsea konishii
• Peumus boldus
• Phoebe grandis
• Sassafras albidum
• Siparuna pauciflora
• Xylopia parviflora

Cross-Links

• PubChem: 248507
• NPASS: NPC13504
• ChEMBL: CHEMBL1321247
• LOTUS: LTS0198439
• wikiData: Q27166971