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(R)-Salsolinol

AlkaPlorer ID: AK009087

Synonym: '(-)-Salsolinol', '(R)-(+)-Salsolinol', 'salsolinol', 'Salsolinol', '1-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline', '(+)-(R)-Salsolinol', '6,7-Isoquinolinediol, 1,2,3,4-tetrahydro-1-methyl-, (S)-', '(+)-Salsolinol'

IUPAC Name: (1S)-1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol

Structure

SMILES: C[C@@H]1NCCC2=CC(O)=C(O)C=C21

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InChI: InChI=1S/C10H13NO2/c1-6-8-5-10(13)9(12)4-7(8)2-3-11-6/h4-6,11-13H,2-3H2,1H3/t6-/m0/s1

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InChIKey: IBRKLUSXDYATLG-LURJTMIESA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Rheum tanguticum Rheum Polygonaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Symploca hydnoides Symploca Microcoleaceae Oscillatoriales Cyanophyceae Cyanobacteriota None Bacteria
Codium decorticatum Codium Codiaceae Bryopsidales Ulvophyceae Chlorophyta Viridiplantae Eukaryota
Citrus glauca Citrus Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Baccharis megapotamica Baccharis Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cryptotermes cynocephalus Cryptotermes Kalotermitidae Blattodea Insecta Arthropoda Metazoa Eukaryota
Orthosphenia mexicana Orthosphenia Celastraceae Celastrales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Haplophyllum dauricum Haplophyllum Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Thuja standishii Thuja Cupressaceae Cupressales Pinopsida Streptophyta Viridiplantae Eukaryota
Critonia quadrangularis Critonia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Rhinoceros sondaicus Rhinoceros Rhinocerotidae Perissodactyla Mammalia Chordata Metazoa Eukaryota
Ficus simplicissima Ficus Moraceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aconitum japonicum Aconitum Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Quercus dentata Quercus Fagaceae Fagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Amanita cokeri Amanita Amanitaceae Agaricales Agaricomycetes Basidiomycota Fungi Eukaryota
Annona reticulata Annona Annonaceae Magnoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Swinglea glutinosa Swinglea Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Theobroma cacao Theobroma Malvaceae Malvales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Asteriscus graveolens Asteriscus Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Marrubium supinum Marrubium Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aconitum sachalinense Aconitum Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Salmonella enterica Salmonella Enterobacteriaceae Enterobacterales Gammaproteobacteria Pseudomonadota None Bacteria
Aconitum carmichaelii Aconitum Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Oxyanthus speciosus Oxyanthus Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Styrax perkinsiae Styrax Styracaceae Ericales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Strychnos tabascana Strychnos Loganiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Streptomyces xantholiticus Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Senecio latifolius Senecio Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ceratozamia fuscoviridis Ceratozamia Zamiaceae Cycadales Cycadopsida Streptophyta Viridiplantae Eukaryota
Solanum elaeagnifolium Solanum Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aconitum kusnezoffii Aconitum Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Portulaca oleracea Portulaca Portulacaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aconitum ciliare Aconitum Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Bombus muscorum Bombus Apidae Hymenoptera Insecta Arthropoda Metazoa Eukaryota
Centrosema pascuorum Centrosema Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Flemingia congesta Flemingia Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 179.219

TPSA？: 52.49

MolLogP？: 1.3045

Number of H-Donors: 3

Number of H-Acceptors: 3

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus subtilis 4'-phosphopantetheinyl transferase ffp Potency 35481.3 nM None
Homo sapiens Alpha-1b adrenergic receptor Activity 19.2 % 10.1021/acs.jnatprod.9b00418
Homo sapiens Ataxin-2 Potency 15848.9 nM None
Homo sapiens Beta-1 adrenergic receptor Activity -9.5 % 10.1021/acs.jnatprod.9b00418
Homo sapiens Beta-2 adrenergic receptor Activity 35.5 % 10.1021/acs.jnatprod.7b00762
Homo sapiens Cytochrome P450 1A2 AC50 nan None None
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 AC50 15848.93 nM None
Homo sapiens Cytochrome P450 2C9 Potency 15848.9 nM None
Homo sapiens Cytochrome P450 2D6 AC50 nan None None
Homo sapiens Cytochrome P450 3A4 AC50 nan None None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 15848.9 nM None
Homo sapiens Dopamine D2 receptor Ki 5000.0 nM 10.1021/np4009927
Homo sapiens Dopamine D3 receptor Ki 500.0 nM 10.1021/np4009927
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 251.2 nM None
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 6309.6 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 11220.2 nM None
Homo sapiens Thyroid stimulating hormone receptor Potency 12589.3 nM None
Mus musculus RAW264.7 EC50 58700.0 nM 10.1021/acs.jnatprod.7b00762
Mus musculus RAW264.7 Inhibition nan % 10.1021/acs.jnatprod.7b00762
Rattus norvegicus Rattus norvegicus Activity 21.5 nM 10.1021/np4009927

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT013021 C[C@@H]1NCCc2cc(O)c(O)cc21>>CC=O MNXR103573
AKRT013022 C[C@@H]1NCCc2cc(O)c(O)cc21>>NCCc1ccc(O)c(O)c1 MNXR103573
AKRT014574 C[SAH].C[C@@H]1NCCc2cc(O)c(O)cc21>>COc1cc2c(cc1O)CCN[C@H]2C MNXR103577
AKRT014575 C[SAH].C[C@@H]1NCCc2cc(O)c(O)cc21>>C[C@@H]1c2ccc(O)c(O)c2CCN1C MNXR103663
AKRT014576 C[SAH].C[C@@H]1NCCc2cc(O)c(O)cc21>>C[C@H]1c2cc(O)c(O)cc2CCN1C MNXR103578