(+)-Norephedrine

AlkaPlorer ID: AK008659

Synonym: 'Norephedrine', '', 'pseudonorephedrine', 'Mucorama', 'DL-Phenylpropanolamine', 'L-Phenyl Propanolamine', 'd-Norephedrine', 'Obestat', '(+)-Norephedrine', 'norpseudoephedrine', '(+)-Norpseudoephedrine', 'Prestwick_388', 'Propadrine', 'Nobese', 'Cathine', 'Hydriatine', 'L-NOREPHEDRINE', 'D-Cathine', 'DL-Norephedrine'

IUPAC Name: [(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]azanium

Structure

SMILES: C[C@@H]([NH3+])[C@@H](O)C1=CC=CC=C1

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InChI: InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/p+1/t7-,9-/m1/s1

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InChIKey: DLNKOYKMWOXYQA-VXNVDRBHSA-O

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Eulophia spectabilis Eulophia Orchidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ephedra distachya Ephedra Ephedraceae Ephedrales Gnetopsida Streptophyta Viridiplantae Eukaryota
Bupleurum sibiricum Bupleurum Apiaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ephedra saxatilis Ephedra Ephedraceae Ephedrales Gnetopsida Streptophyta Viridiplantae Eukaryota
Ephedra tweediana Ephedra Ephedraceae Ephedrales Gnetopsida Streptophyta Viridiplantae Eukaryota
Euphorbia serrula Euphorbia Euphorbiaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Omphalotus japonicus Omphalotus Omphalotaceae Agaricales Agaricomycetes Basidiomycota Fungi Eukaryota
Ephedra gerardiana Ephedra Ephedraceae Ephedrales Gnetopsida Streptophyta Viridiplantae Eukaryota
Ephedra major Ephedra Ephedraceae Ephedrales Gnetopsida Streptophyta Viridiplantae Eukaryota
Thymus vulgaris Thymus Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ephedra intermedia Ephedra Ephedraceae Ephedrales Gnetopsida Streptophyta Viridiplantae Eukaryota
Berberis empetrifolia Berberis Berberidaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Mikania cordata Mikania Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ephedra sinica Ephedra Ephedraceae Ephedrales Gnetopsida Streptophyta Viridiplantae Eukaryota
Ephedra regeliana Ephedra Ephedraceae Ephedrales Gnetopsida Streptophyta Viridiplantae Eukaryota
Ephedra equisetina Ephedra Ephedraceae Ephedrales Gnetopsida Streptophyta Viridiplantae Eukaryota
Veronica longifolia Veronica Plantaginaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ephedra monosperma Ephedra Ephedraceae Ephedrales Gnetopsida Streptophyta Viridiplantae Eukaryota
Homo sapiens Homo Hominidae Primates Mammalia Chordata Metazoa Eukaryota
Ephedra przewalskii Ephedra Ephedraceae Ephedrales Gnetopsida Streptophyta Viridiplantae Eukaryota
Ephedra likiangensis Ephedra Ephedraceae Ephedrales Gnetopsida Streptophyta Viridiplantae Eukaryota
Thymus quinquecostatus Thymus Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ephedra sp. Ephedra Ephedraceae Ephedrales Gnetopsida Streptophyta Viridiplantae Eukaryota
Catha edulis Catha Celastraceae Celastrales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Tilia americana Tilia Malvaceae Malvales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Allium atroviolaceum Allium Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Stylissa massa Stylissa Axinellidae Axinellida Demospongiae Porifera Metazoa Eukaryota

Properties Information

Molecule Weight: 152.21699999999998

TPSA: 47.870000000000005

MolLogP: 0.3503999999999995

Number of H-Donors: 2

Number of H-Acceptors: 1

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bos taurus Phenylethanolamine N-methyltransferase Ki 2980000.0 nM 10.1021/jm00118a021
Homo sapiens Histone deacetylase 6 Inhibition -5.79 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 0.41 % 10.6019/CHEMBL4808148
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
None No relevant target pKa 9.05 None 10.1007/s11095-013-1232-z

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT012787 C[C@@H](N)[C@@H](O)c1ccccc1>>CC(=N)C(O)c1ccccc1 enzymemap_22897
AKRT013665 C[C@H](N)C(=O)c1ccccc1>>C[C@@H](N)[C@@H](O)c1ccccc1 MNXR150279
AKRT014572 C[SAH].C[C@@H](N)[C@@H](O)c1ccccc1>>CN[C@@H](C)[C@H](O)c1ccccc1 MNXR150281