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Boldine

AlkaPlorer ID: AK002025

Synonym: None

IUPAC Name: (6aS)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol

Structure

SMILES: COC1=C(O)C=C2C[C@H]3C4=C(C2=C1)C(OC)=C(O)C=C4CCN3C

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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/t13-/m0/s1

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InChIKey: LZJRNLRASBVRRX-ZDUSSCGKSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Alpinia pricei Alpinia Zingiberaceae Zingiberales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Vachellia karroo Vachellia Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ormosia fordiana Ormosia Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Sassafras albidum Sassafras Lauraceae Laurales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ficus septica Ficus Moraceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Nalanthamala diospyri Nalanthamala Nectriaceae Hypocreales Sordariomycetes Ascomycota Fungi Eukaryota
Beilschmiedia kunstleri Beilschmiedia Lauraceae Laurales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lindera aggregata Lindera Lauraceae Laurales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Podocarpus elatus Podocarpus Podocarpaceae Araucariales Pinopsida Streptophyta Viridiplantae Eukaryota
Lippia graveolens Lippia Verbenaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ferulago sylvatica Ferulago Apiaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cephalaria leucantha Cephalaria Caprifoliaceae Dipsacales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Crinum stuhlmannii Crinum Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Metrodorea flavida Metrodorea Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Gordonia terrae Gordonia Gordoniaceae Mycobacteriales Actinomycetes Actinomycetota None Bacteria
Bursera simaruba Bursera Burseraceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Diplacus aurantiacus Diplacus Phrymaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Polygala senega Polygala Polygalaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Seiridium cardinale Seiridium Sporocadaceae Xylariales Sordariomycetes Ascomycota Fungi Eukaryota
Ericameria laricifolia Ericameria Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ramalina farinacea Ramalina Ramalinaceae Lecanorales Lecanoromycetes Ascomycota Fungi Eukaryota
Vismia macrophylla Vismia Hypericaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Streptomyces nigrescens Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Cissus quadrangularis Cissus Vitaceae Vitales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Litsea cubeba Litsea Lauraceae Laurales Magnoliopsida Streptophyta Viridiplantae Eukaryota
None Nectandra Lauraceae Laurales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Metadina trichotoma Metadina Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Polanisia trachysperma Polanisia Cleomaceae Brassicales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Delphinium denudatum Delphinium Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Neolitsea dealbata Neolitsea Lauraceae Laurales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Palaquium leiocarpum Palaquium Sapotaceae Ericales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Angelica pachycarpa Angelica Apiaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Curcuma wenyujin Curcuma Zingiberaceae Zingiberales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Paeonia officinalis Paeonia Paeoniaceae Saxifragales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 327.3800000000001

TPSA？: 62.16

MolLogP？: 2.867100000000001

Number of H-Donors: 2

Number of H-Acceptors: 5

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus anthracis Anthrax lethal factor Potency 25118.9 nM None
Bos taurus Mitochondrial peptide methionine sulfoxide reductase IC50 47814.0 nM None
Chlorocebus sabaeus Vero CC50 250000.0 nM 10.1021/np970382v
Chlorocebus sabaeus Vero MTC 125.0 uM 10.1021/np970382v
Electrophorus electricus Acetylcholinesterase Inhibition 9.51 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 1.24 % 10.1016/j.bmc.2012.09.040
Homo sapiens 15-hydroxyprostaglandin dehydrogenase [NAD+] Potency 14125.4 nM None
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 10000.0 nM None
Homo sapiens Ataxin-2 Potency 15848.9 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 12990.0 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 35481.3 nM None
Homo sapiens Casein kinase 2 IC50 700.0 nM 10.1021/acs.jnatprod.8b00889
Homo sapiens Cytochrome P450 1A2 AC50 2511.89 nM None
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 Potency 31622.8 nM None
Homo sapiens Cytochrome P450 2D6 AC50 6309.57 nM None
Homo sapiens Cytochrome P450 2D6 Potency 6309.6 nM None
Homo sapiens Cytochrome P450 2D6 Potency 7943.3 nM None
Homo sapiens Cytochrome P450 3A4 AC50 15848.93 nM None
Homo sapiens Cytochrome P450 3A4 Potency 15848.9 nM None
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 12589.3 nM None
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 31622.8 nM None
Homo sapiens Geminin Potency 6513.1 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 3548.1 nM None
Homo sapiens Hypoxia-inducible factor 1 alpha Potency 1995.3 nM None
Homo sapiens Lysine-specific demethylase 4D-like Potency 8912.5 nM None
Homo sapiens Neuronal acetylcholine receptor; alpha4/beta2 IC50 10000.0 nM 10.1016/j.bmc.2007.03.023
Homo sapiens Neuronal acetylcholine receptor; alpha4/beta2 Ki 3000.0 nM 10.1016/j.bmc.2007.03.023
Homo sapiens Neuronal acetylcholine receptor protein alpha-7 subunit IC50 81000.0 nM 10.1016/j.bmc.2007.03.023
Homo sapiens Neuronal acetylcholine receptor protein alpha-7 subunit Ki 67000.0 nM 10.1016/j.bmc.2007.03.023
Homo sapiens Prelamin-A/C Potency 316.2 nM None
Homo sapiens Sclerostin IC50 5000.0 nM None
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 47.95 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 100.1 % 10.1124/mol.112.084152
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 reverse transcriptase IC50 200.0 ug.mL-1 10.1021/np50073a012
Plasmodium falciparum Plasmodium falciparum IC50 1.47 ug.mL-1 10.1021/np960195h
Plasmodium falciparum Plasmodium falciparum IC50 2.13 ug.mL-1 10.1021/np960195h
Plasmodium falciparum Plasmodium falciparum Potency 18526.0 nM None
Poliovirus 2 Poliovirus 2 Activity nan None 10.1021/np970382v
Poliovirus 2 Poliovirus 2 ED50 125.0 uM 10.1021/np970382v
Rattus norvegicus Alpha-1a adrenergic receptor Ki 4.898 nM 10.1021/np990433j
Rattus norvegicus Alpha-1b adrenergic receptor Ki 316.23 nM 10.1021/np990433j
Rattus norvegicus Dopamine D1 receptor IC50 400.0 nM 10.1021/jm060959i
Rattus norvegicus Dopamine D1 receptor IC50 400.0 nM 10.1021/np990433j
Rattus norvegicus Dopamine D1 receptor Ki 290.0 nM 10.1021/jm060959i
Rattus norvegicus Dopamine D2 receptor IC50 500.0 nM 10.1021/jm060959i
Rattus norvegicus Dopamine D2 receptor IC50 520.0 nM 10.1021/np990433j
Rattus norvegicus Dopamine D2 receptor Ki 370.0 nM 10.1021/jm060959i
Rattus norvegicus Dual specificity tyrosine-phosphorylation-regulated kinase 1A AC50 4838.0 nM None
Rattus norvegicus Rattus norvegicus Activity 25.0 % 10.1021/jm060959i
Rattus norvegicus Rattus norvegicus Activity 50.0 % 10.1021/jm060959i
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 17782.8 nM None
None Unchecked AC50 23870.0 nM None
None Unchecked Potency 446.7 nM None
None Unchecked Ratio 2.0 None 10.1021/np970382v
None Unchecked Ratio 70.0 None 10.1021/np990433j
None Unchecked Ratio IC50 1.3 None 10.1021/np990433j

Metabolism Information