EPHEDRINE

ID: ALA211456

Max Phase: Approved

First Approval: 2016

Molecular Formula: C10H15NO

Molecular Weight: 165.24

Molecule Type: Small molecule

Associated Items:

Representations

Synonyms (8): (-)-ephedrine | Ephedrine | Ephedrine, anhydrous | Ephedrinum, anhydrous | L-ephedrine | Xenadrine | NSC-170951 | NSC-8971
Synonyms from Alternative Forms(8):

    Canonical SMILES:  CN[C@@H](C)[C@H](O)c1ccccc1

    Standard InChI:  InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1

    Standard InChI Key:  KWGRBVOPPLSCSI-WPRPVWTQSA-N

    Associated Targets(Human)

    Homo sapiens 32628 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Skin 286 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Whole blood 398 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Phosphatidylinositol-3,4,5-trisphosphate 5-phosphatase 1 17 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2 180 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Histone deacetylase 6 20808 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Histamine H2 receptor 5428 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dopamine D1 receptor 9720 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    HERG 29587 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Beta-1 adrenergic receptor 6630 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Beta-2 adrenergic receptor 11824 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dopamine transporter 10535 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Neuronal acetylcholine receptor protein alpha-4 subunit 1265 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dopamine D4 receptor 7907 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Neurokinin 1 receptor 6273 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Kappa opioid receptor 16155 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 2c (5-HT2c) receptor 11471 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Adenosine A1 receptor 17603 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Adenosine A3 receptor 15931 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Muscarinic acetylcholine receptor M1 12690 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Muscarinic acetylcholine receptor M3 7750 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Alpha-1a adrenergic receptor 8359 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dopamine D2 receptor 23596 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Equilibrative nucleoside transporter 1 1711 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Alpha-2b adrenergic receptor 4412 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Norepinephrine transporter 10102 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Alpha-2c adrenergic receptor 4876 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 3a (5-HT3a) receptor 3366 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin transporter 12625 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Adenosine A2a receptor 16305 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Beta-3 adrenergic receptor 5850 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Hydroxycarboxylic acid receptor 2 1903 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Delta opioid receptor 15096 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Thromboxane A2 receptor 5717 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Alpha-2a adrenergic receptor 9450 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Mu opioid receptor 19785 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Sodium channel protein type V alpha subunit 3462 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Monoamine oxidase A 11911 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Gastric inhibitory polypeptide receptor 542 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Vasopressin V1a receptor 5412 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Vasopressin V2 receptor 2912 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 2b (5-HT2b) receptor 10323 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 1a (5-HT1a) receptor 14969 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cyclooxygenase-2 13999 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Estrogen receptor alpha 17718 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Bradykinin B2 receptor 3970 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cholecystokinin B receptor 3550 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Glucagon receptor 2563 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Ghrelin receptor 6229 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 2a (5-HT2a) receptor 14758 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Estrogen receptor beta 9272 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Glucocorticoid receptor 14987 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Type-1 angiotensin II receptor 5176 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cholecystokinin A receptor 4460 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Endothelin receptor ET-A 5008 Activities

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    Endothelin receptor ET-B 1928 Activities

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    Cannabinoid CB1 receptor 20913 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Bradykinin B1 receptor 1859 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Corticotropin releasing factor receptor 1 2996 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Corticotropin releasing factor receptor 2 399 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Melanocortin receptor 3 5659 Activities

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    Melanocortin receptor 4 10016 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Phosphodiesterase 4D 3546 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Neuropeptide Y receptor type 1 5019 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Motilin receptor 1724 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Neurotensin receptor 1 1525 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Phosphodiesterase 3A 3309 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Neuropeptide Y receptor type 2 3731 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Progesterone receptor 8562 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dopamine D3 receptor 14368 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Muscarinic acetylcholine receptor M2 10671 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Histamine H3 receptor 10389 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Histamine H1 receptor 7573 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Associated Targets(non-human)

    Canis familiaris 36305 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Colon 38 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Small intestine 70 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Rattus norvegicus 775804 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    SARS-CoV-2 38078 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Voltage-gated L-type calcium channel alpha-1C subunit 1321 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Glutamate (NMDA) receptor subunit zeta 1 2166 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    GABA receptor alpha-1 subunit 2848 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Voltage-gated N-type calcium channel alpha-1B subunit 471 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Cyclooxygenase-1 1373 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Androgen Receptor 5522 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Molecule Features

    Natural Product: YesOral: NoChemical Probe: NoParenteral: Yes
    Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
    Chirality: YesAvailability: NoProdrug: No

    Drug Indications

    MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

    Mechanisms of Action

    Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

    Properties

    Molecular Weight: 165.24Molecular Weight (Monoisotopic): 165.1154AlogP: 1.33#Rotatable Bonds: 3
    Polar Surface Area: 32.26Molecular Species: BASEHBA: 2HBD: 2
    #RO5 Violations: 0HBA (Lipinski): 2HBD (Lipinski): 2#RO5 Violations (Lipinski): 0
    CX Acidic pKa: 13.89CX Basic pKa: 9.52CX LogP: 1.32CX LogD: -0.78
    Aromatic Rings: 1Heavy Atoms: 12QED Weighted: 0.71Np Likeness Score: 0.43

    References

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    3. Shimojima Y, Shirai T, Baba T, Hayashi H..  (1985)  1H-2-Benzopyran-1-one derivatives, microbial products with pharmacological activity. Conversion into orally active derivatives with antiinflammatory and antiulcer activities.,  28  (1): [PMID:3965711] [10.1021/jm00379a002]
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    5. Ottaviani G, Martel S, Carrupt PA..  (2006)  Parallel artificial membrane permeability assay: a new membrane for the fast prediction of passive human skin permeability.,  49  (13): [PMID:16789751] [10.1021/jm060230+]
    6. Ottaviani G, Martel S, Carrupt PA..  (2007)  In silico and in vitro filters for the fast estimation of skin permeation and distribution of new chemical entities.,  50  (4): [PMID:17300161] [10.1021/jm0611105]
    7. Baert B, Deconinck E, Van Gele M, Slodicka M, Stoppie P, Bodé S, Slegers G, Vander Heyden Y, Lambert J, Beetens J, De Spiegeleer B..  (2007)  Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds.,  15  (22): [PMID:17827020] [10.1016/j.bmc.2007.07.050]
    8. Gozalbes R, Pineda-Lucena A..  (2010)  QSAR-based solubility model for drug-like compounds.,  18  (19): [PMID:20810286] [10.1016/j.bmc.2010.08.003]
    9. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]
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    13. Settimo L, Bellman K, Knegtel RM..  (2013)  Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.,  [PMID:24249037] [10.1007/s11095-013-1232-z]
    14. Settimo L, Bellman K, Knegtel RM..  (2013)  Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.,  [PMID:24249037] [10.1007/s11095-013-1232-z]
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    23. Unpublished dataset, 
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    26. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]
    27. Unpublished dataset, 
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