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Hyoscyamine

AlkaPlorer ID: AK003832

Synonym: None

IUPAC Name: [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenylpropanoate

Structure

SMILES: CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)[C@H](CO)C1=CC=CC=C1)C2

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InChI: InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1

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InChIKey: RKUNBYITZUJHSG-FXUDXRNXSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Byssomerulius corium Byssomerulius Irpicaceae Polyporales Agaricomycetes Basidiomycota Fungi Eukaryota
Doris odhneri Doris Dorididae Nudibranchia Gastropoda Mollusca Metazoa Eukaryota
Peucedanum officinale Peucedanum Apiaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Saussurea laniceps Saussurea Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Botrylloides leachii Botrylloides Styelidae Stolidobranchia Ascidiacea Chordata Metazoa Eukaryota
Sargassum yezoense Sargassum Sargassaceae Fucales Phaeophyceae None None Eukaryota
Scopolia carniolica Scopolia Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Euphorbia stepposa Euphorbia Euphorbiaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Mimosa pudica Mimosa Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Celastrus rosthornianus Celastrus Celastraceae Celastrales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Sanicula europaea Sanicula Apiaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Physochlaina orientalis Physochlaina Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Penicillium aragonense Penicillium Aspergillaceae Eurotiales Eurotiomycetes Ascomycota Fungi Eukaryota
Stevia tomentosa Stevia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Callitris drummondii Callitris Cupressaceae Cupressales Pinopsida Streptophyta Viridiplantae Eukaryota
Leiothrix curvifolia Leiothrix Eriocaulaceae Poales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ilex canariensis Ilex Aquifoliaceae Aquifoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ipomopsis aggregata Ipomopsis Polemoniaceae Ericales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Paeonia emodi Paeonia Paeoniaceae Saxifragales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Streptomyces flaveolus Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Cipadessa baccifera Cipadessa Meliaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Achillea atrata Achillea Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Vespa orientalis Vespa Vespidae Hymenoptera Insecta Arthropoda Metazoa Eukaryota
Penicillium raistrickii Penicillium Aspergillaceae Eurotiales Eurotiomycetes Ascomycota Fungi Eukaryota
Capuronianthus mahafalensis Capuronianthus Meliaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Potentilla argentea Potentilla Rosaceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Datura inoxia Datura Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lavandula multifida Lavandula Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Podocarpus philippinensis Podocarpus Podocarpaceae Araucariales Pinopsida Streptophyta Viridiplantae Eukaryota
Bazzania trilobata Bazzania Lepidoziaceae Jungermanniales Jungermanniopsida Streptophyta Viridiplantae Eukaryota
Streptomyces fulvoviridis Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Chenopodium album Chenopodium Chenopodiaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ulva reticulata Ulva Ulvaceae Ulvales Ulvophyceae Chlorophyta Viridiplantae Eukaryota
Tecomella undulata Tecomella Bignoniaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Terpios hoshinota Terpios None Suberitida Demospongiae Porifera Metazoa Eukaryota
Viscum articulatum Viscum Viscaceae Santalales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Metapochonia suchlasporia Metapochonia Clavicipitaceae Hypocreales Sordariomycetes Ascomycota Fungi Eukaryota
Pelargonium quercifolium Pelargonium Geraniaceae Geraniales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Alternaria radicina Alternaria Pleosporaceae Pleosporales Dothideomycetes Ascomycota Fungi Eukaryota

Properties Information

Molecule Weight: 289.37500000000006

TPSA？: 49.77

MolLogP？: 1.9309

Number of H-Donors: 1

Number of H-Acceptors: 4

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Electrophorus electricus Acetylcholinesterase Inhibition 15.53 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 3.5 % 10.1016/j.bmc.2012.09.040
Escherichia coli K-12 Beta-lactamase AmpC Potency 8912.5 nM None
Homo sapiens Adenosine A1 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A2a receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A3 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-1a adrenergic receptor AC50 23999.9 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-1a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2b adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2c adrenergic receptor AC50 29000.1 nM 10.1038/s41467-023-40064-9
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 1031.8 nM None
Homo sapiens Beta-1 adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-2 adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Bile salt export pump AC50 300000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Bile salt export pump IC50 1000000.0 nM 10.1124/dmd.112.047068
Homo sapiens Bradykinin B2 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cannabinoid CB1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cholecystokinin A receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cyclooxygenase-2 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Delta opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens DNA polymerase iota Potency 89125.1 nM None
Homo sapiens Dopamine D1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine transporter AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Equilibrative nucleoside transporter 1 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Estrogen receptor alpha AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Geminin Potency 183.6 nM None
Homo sapiens Ghrelin receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Glucocorticoid receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 Potency 6513.1 nM None
Homo sapiens HERG AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H1 receptor AC50 3394.1 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Kappa opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Melanocortin receptor 3 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Melanocortin receptor 4 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Monoamine oxidase A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Motilin receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 6.3 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 7.4 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 6.3 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 16.7 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M3 AC50 4.1 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuronal acetylcholine receptor protein alpha-4 subunit AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuropeptide Y receptor type 1 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Norepinephrine transporter AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 3A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4D AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Pregnane X receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Progesterone receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serine/threonine-protein kinase PLK1 Potency 29934.9 nM None
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2a (5-HT2a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2c (5-HT2c) receptor AC50 26999.8 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 3a (5-HT3a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin transporter AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 97.76 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 102.17 % 10.1124/mol.112.084152
Homo sapiens Thromboxane A2 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Type-1 angiotensin II receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vasopressin V1a receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vasopressin V2 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Plasmodium falciparum Plasmodium falciparum Potency 2936.2 nM None
Rattus norvegicus Androgen Receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Cyclooxygenase-1 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus GABA receptor alpha-1 subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Glutamate (NMDA) receptor subunit zeta 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Voltage-gated L-type calcium channel alpha-1C subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 28.35 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.0469 None 10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.15 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.25 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition index 0.2122 None 10.1101/2020.04.03.023846

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT010517 CN1C2CC(O)C1C[C@@H](OC(=O)[C@@H](CO)c1ccccc1)C2>>CN1[C@H]2CC[C@@H]1C[C@H](OC(=O)[C@H](CO)c1ccccc1)C2 MNXR192149
AKRT010597 CN1[C@H]2CC[C@@H]1C[C@H](O)C2.O=C(O)C(CO)c1ccccc1>>CN1[C@H]2CC[C@@H]1C[C@H](OC(=O)[C@H](CO)c1ccccc1)C2 MNXR148237
AKRT010603 CN1[C@H]2CC[C@@H]1C[C@H](OC(=O)[C@H](C=O)c1ccccc1)C2>>CN1[C@H]2CC[C@@H]1C[C@H](OC(=O)[C@H](CO)c1ccccc1)C2 R08434
AKRT010604 CN1[C@H]2CC[C@@H]1C[C@H](OC(=O)[C@H](CO)c1ccccc1)C2.O=C(O)CCC(=O)C(=O)O>>CN1[C@@H]2C[C@@H](OC(=O)[C@H](CO)c3ccccc3)C[C@H]1C[C@@H]2O.O=C(O)CCC(=O)O.O=C=O None
AKRT010605 CN1[C@H]2CC[C@@H]1C[C@H](OC(=O)[C@H](CO)c1ccccc1)C2>>CN1C2CC(O)C1C[C@@H](OC(=O)C(CO)c1ccccc1)C2 R03812
AKRT010606 CN1[C@H]2CC[C@@H]1C[C@H](OC(=O)[C@H](CO)c1ccccc1)C2>>CN1[C@H]2CC[C@@H]1C[C@H](O)C2 enzymemap_51538
AKRT010607 CN1[C@H]2CC[C@@H]1C[C@H](OC(=O)[C@H](CO)c1ccccc1)C2>>CN1[C@H]2C[C@H](OC(=O)[C@H](CO)c3ccccc3)C[C@@H]1[C@@H](O)C2 HYOSCYAMINE-6-DIOXYGENASE-RXN
AKRT010608 CN1[C@H]2CC[C@@H]1C[C@H](OC(=O)[C@H](CO)c1ccccc1)C2>>O=C(O)[C@H](CO)c1ccccc1 enzymemap_51538
AKRT010610 CN1[C@H]2CC[C@@H]1C[C@H](OC(=O)[C@H](O)Cc1ccccc1)C2>>CN1[C@H]2CC[C@@H]1C[C@H](OC(=O)[C@H](CO)c1ccccc1)C2 RXN-8255
AKRT010613 CN1[C@H]2C[C@H](OC(=O)[C@H](CO)c3ccccc3)C[C@@H]1[C@@H](O)C2>>CN1[C@H]2CC[C@@H]1C[C@H](OC(=O)[C@H](CO)c1ccccc1)C2 enzymemap_10553