SALVINORIN A

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category UNKNOWN
UNII T56W91NG6J
EPA CompTox DTXSID80232584

Structure

InChI Key OBSYBRPAKCASQB-AGQYDFLVSA-N
Smiles COC(=O)[C@@H]1C[C@H](OC(C)=O)C(=O)[C@H]2[C@@]1(C)CC[C@H]1C(=O)O[C@H](c3ccoc3)C[C@]21C
InChI
InChI=1S/C23H28O8/c1-12(24)30-16-9-15(20(26)28-4)22(2)7-5-14-21(27)31-17(13-6-8-29-11-13)10-23(14,3)19(22)18(16)25/h6,8,11,14-17,19H,5,7,9-10H2,1-4H3/t14-,15-,16-,17-,19-,22-,23-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H28O8
Molecular Weight 432.47
AlogP 3.0
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 3.0
Polar Surface Area 109.11
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 31.0
Assay Description Organism Bioactivity Reference
Inhibition of [125I]- IOXY binding to human Opioid receptor kappa1 Homo sapiens 1.9 nM Inhibition of [125I]- IOXY binding to human Opioid receptor kappa1 Homo sapiens 38.0 nM
Inhibition of [3H]diprenorphine binding to human Opioid receptor kappa 1 expressed in chinese hamster ovary cells Homo sapiens 1.3 nM
Inhibition of [3H]U-69593 binding to rat opioid receptor kappa 1 expressed in HEK 293 cells Rattus norvegicus 4.0 nM
Stimulation of [35S]GTP-gamma-S, binding to Opioid receptor kappa1 expressed in CHO cells Homo sapiens 40.0 nM
Effective concentration for activation of human Opioid receptor kappa 1 expressed in chinese hamster ovary cells to enhance [35S]GTP-gamma-S, binding Homo sapiens 4.5 nM
Effective concentration of compound against intracellular calcium mobilization in rat Rattus norvegicus 46.0 nM
In vivo antinociceptive activity against opioid receptor in mouse tail flick test Mus musculus 28.0 %
Inhibition of [3H]diprenorphine binding to human KOR expressed in CHO cells Homo sapiens 1.3 nM Inhibition of [3H]diprenorphine binding to human KOR expressed in CHO cells Homo sapiens 2.6 nM
Enhancement of [35S]GTP-gamma-S binding to human KOR expressed in CHO cells Homo sapiens 4.5 nM Enhancement of [35S]GTP-gamma-S binding to human KOR expressed in CHO cells Homo sapiens 2.2 nM
Displacement of [3H]diprenorphine binding from human kappa opioid receptor expressed in CHO cells Homo sapiens 1.3 nM
Binding potency at human kappa opioid receptor expressed in CHO cells by [35S]GTPgammaS binding assay Homo sapiens 4.5 nM
Displacement of [3H]U-69593 from rat cloned KOR Rattus norvegicus 0.75 nM Displacement of [3H]U-69593 from rat cloned KOR Rattus norvegicus 18.4 nM
Activity at human kappa opioid receptor expressed in HEK293 cells as intracellular calcium mobilization Homo sapiens 2.82 nM Activity at human kappa opioid receptor expressed in HEK293 cells as intracellular calcium mobilization Homo sapiens 4.77 nM
Antagonist activity at human kappa opioid receptor expressed in CHO cells by [35S]GTP-gamma-S binding assay Homo sapiens 45.0 nM
Agonist activity at human kappa opioid receptor assessed as inhibition of Galpha-16-induced calcium flux Homo sapiens 1.24 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor expressed in HEK293 cells Rattus norvegicus 17.5 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor I62A mutant expressed in HEK293 cells Rattus norvegicus 22.0 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor Y66A mutant expressed in HEK293 cells Rattus norvegicus 18.1 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor Y66F mutant expressed in HEK293 cells Rattus norvegicus 6.8 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor K227A mutant expressed in HEK293 cells Rattus norvegicus 25.3 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor I290A mutant expressed in HEK293 cells Rattus norvegicus 29.6 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor I294A mutant expressed in HEK293 cells Rattus norvegicus 2.9 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor Q115A mutant expressed in HEK293 cells Rattus norvegicus 147.0 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor Y119A mutant expressed in HEK293 cells Rattus norvegicus 67.0 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor Y119F mutant expressed in HEK293 cells Rattus norvegicus 17.7 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor D138A mutant expressed in HEK293 cells Rattus norvegicus 17.5 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor Y139F mutant expressed in HEK293 cells Rattus norvegicus 9.5 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor E297A mutant expressed in HEK293 cells Rattus norvegicus 19.5 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor Y312A mutant expressed in HEK293 cells Rattus norvegicus 79.0 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor Y312F mutant expressed in HEK293 cells Rattus norvegicus 16.0 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor Y313A mutant expressed in HEK293 cells Rattus norvegicus 126.0 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor Y313F mutant expressed in HEK293 cells Rattus norvegicus 37.0 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor Y320A mutant expressed in HEK293 cells Rattus norvegicus 565.0 nM
Displacement of [3H]diprenorphine from rat kappa opioid receptor Y320F mutant expressed in HEK293 cells Rattus norvegicus 71.0 nM
Displacement of [3H]diprenorphine from chimeric rat kappa opioid receptor (1-141)/mu opioid receptor (151-233)/kappa opioid receptor (228-380) expressed in HEK293 cells Rattus norvegicus 522.0 nM
Displacement of [3H]diprenorphine from chimeric rat mu opioid receptor (1-150)/kappa opioid receptor (142-227)/mu opioid receptor (234-398) expressed in HEK293 cells Rattus norvegicus 458.0 nM
Displacement of [3H]diprenorphine from human kappa opioid receptor expressed in CHO cells Homo sapiens 2.4 nM
Agonist activity at human kappa opioid receptor expressed in CHO cells assessed as stimulation of [35S]GTPgammaS binding Homo sapiens 1.8 nM
Displacement of [125I]IOXY from human recombinant kappa opioid receptor expressed in CHO cells Homo sapiens 1.9 nM Displacement of [125I]IOXY from human recombinant kappa opioid receptor expressed in CHO cells Homo sapiens 5.7 nM
Agonist activity at human recombinant kappa opioid receptor expressed in CHO cells by [35S]GTP-gamma-S binding assay Homo sapiens 40.0 nM
Displacement of [3H]diprenorphine from human KOPR expressed in CHO cells Homo sapiens 2.5 nM
Agonist activity at human KOPR expressed in CHO cells assessed as enhancement of [35S]GTPgammaS binding Homo sapiens 2.1 nM
Displacement of [125]OXY from kappa opioid receptor None 1.9 nM
Agonist activity at human kappa opioid receptor expressed in CHO cells by [35S]GTPgammaS binding Homo sapiens 45.0 nM
Agonist activity at human kappa opioid receptor-Galpha-16 fusion protein expressed in CHO cells by calcium flux assay Homo sapiens 0.81 nM
Displacement of [3H]U69593 from kappa opioid receptor expressed in HEK293 cells by visible spectrophotometry None 0.8 nM
Binding affinity to kappa opioid receptor None 1.9 nM
Agonist activity at human kappa opioid receptor expressed in CHO cells assessed as increase of [35S]GTPgammaS binding Homo sapiens 7.5 nM
Displacement of [3H]diprenorphine from human kappa opioid receptor expressed in CHO cells at 3 uM Homo sapiens 50.0 %
Displacement of [3H]U69593 from kappa opioid receptor expressed in HEK293 cells None 0.75 nM
Agonist activity at kappa opioid receptor expressed in HEK293 cells by [35S]GTPgammaS binding assay None 0.2 nM
Displacement of [3H]U69593 from kappa opioid receptor None 7.4 nM
Agonist activity at human KOPR expressed in U2OS cells assessed as beta-arrestin2 recruitment after 90 mins by DiscoveRx PathHunter assay Homo sapiens 31.0 nM
Agonist activity at human KOPR expressed in CHO cells assessed as [35S]GTPgammaS binding after 60 mins by liquid scintillation counting Homo sapiens 6.9 nM
Displacement of [3H]diprenorphine from human KOPR expressed in CHO cells Homo sapiens 3.0 nM
Displacement of [3H]diprenorphine from rat MOPR expressed in CHO cells at 3 uM Rattus norvegicus 50.0 %
Agonist activity at human recombinant kappa opioid receptor expressed in CHO cells assessed as [35S]GTP-gamma-S binding after 3 hrs by liquid scintillation counting Homo sapiens 40.0 nM
Displacement of [3H]U69593 from human recombinant kappa opioid receptor expressed in CHO cells after 2 hrs by liquid scintillation counting Homo sapiens 7.4 nM
Agonist activity at human recombinant kappa opioid receptor expressed in CHO cells assessed as calcium mobilization after 1 hrs by fluorescence analysis Homo sapiens 6.11 nM
Agonist activity at kappa opioid receptor in human HEK293 cells assessed as stimulation of Galphai signaling by cAMP assay Homo sapiens 5.0 nM
Displacement of [3H]U69593 from kappa opioid receptor (unknown origin) Homo sapiens 6.2 nM
Displacement of [3H]U69593 from kappa opioid receptor (unknown origin) Homo sapiens 3.162 nM Displacement of [3H]U69593 from kappa opioid receptor (unknown origin) Homo sapiens 3.2 nM
Binding affinity to kappa opioid receptor (unknown origin) expressed in HEK293 cells by radioligand displacement assay Homo sapiens 16.0 nM
Displacement of [3H]U69593 from kappa opioid receptor (unknown origin) expressed in HEK293T cells after 1.5 hrs by radioligand binding assay Homo sapiens 2.9 nM
Inhibition of human kappa opioid receptor expressed in HEK293T cells assessed as inhibition of cAMP production after 30 mins Homo sapiens 0.36 nM
Agonist activity at KOR (unknown origin) Homo sapiens 40.0 nM
Agonist activity at human KOR expressed in CHO cells assessed as inhibition of forskolin-induced cAMP accumulation after 30 mins by luminescence assay Homo sapiens 0.03 nM
Agonist activity at human kappa opioid receptor expressed CHO cells co-expressing Galphaq16 assessed as calcium mobilization by fluorescence assay Homo sapiens 1.7 nM
Displacement of [3H]diprenorphine from human kappa opioid receptor expressed in CHO cell membranes Homo sapiens 1.3 nM
Agonist activity at human kappa opioid receptor expressed in CHO cell membranes assessed as stimulation of [35S]GTPgammaS binding Homo sapiens 4.5 nM
Displacement of [3H]diprenorphine from human kappa opioid receptor expressed in CHO cell membranes at 3 uM Homo sapiens 50.0 %
Displacement of [3H]diprenorphine from FLAG-tagged mouse delta opioid receptor expressed in CHO cell membranes Displacement of [3H]diprenorphine from human kappa opioid receptor expressed in CHO cell membranes at 3 uM Mus musculus 50.0 %
Displacement of [3H]diprenorphine from rat mu opioid receptor expressed in CHO cell membranes Displacement of [3H]diprenorphine from human kappa opioid receptor expressed in CHO cell membranes at 3 uM Rattus norvegicus 50.0 %
Agonist activity at human kappa-type opioid receptor expressed in CHO-K1 cells assessed as forskolin-induced cAMP accumulation after 30 mins in presence of forskolin by luminescence-based HitHunter cAMP assay Homo sapiens 0.21 nM
Agonist activity at human kappa-type opioid receptor expressed in CHO-K1 cells assessed as inhibition of forskolin-induced cAMP accumulation after 30 mins by luminescence-based assay Homo sapiens 0.042 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 9.21 %
Agonist activity at kappa opioid receptor (unknown origin) assessed as increase in venus-tagged N-terminal beta-arrestin-2 recruitment by BRET assay Homo sapiens 10.0 nM
Agonist activity at kappa opioid receptor (unknown origin) expressed in HEK cells co-expressing luciferase based cAMP biosensor assessed as increase in cAMP accumulation after 20 to 30 mins by luciferase reporter gene assay Homo sapiens 4.7 nM
Agonist activity at human KOR expressed in HEK293T cells assessed as inhibition of Galphai-mediated cAMP accumulation after 15 mins by microbeta counting assay Homo sapiens 0.015 nM
Agonist activity at Tango-KOR (unknown origin) expressed in HTLA cells harboring TEV-fused-beta-arrestin 2 assessed as increase in beta arrestin 2 recruitment after overnight incubation by BrightGlo reagent based assay Homo sapiens 5.1 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 14.76 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.02 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.02 %
Agonist activity at human KOR expressed in CHOK1 cells assessed as inhibition of forskolin-stimulated cAMP accumulation incubated for 30 mins by luminescence assay Homo sapiens 0.03 nM
Agonist activity at human kappa opiod receptor expressed in CHO-K1 cells assessed as increase in forskolin induced cAMP production measured after 30 mins by HitHunter luminescence based assay Homo sapiens 0.04 nM

Cross References

Resources Reference
ChEBI 67900
ChEMBL CHEMBL445332
DrugBank DB12327
FDA SRS T56W91NG6J
Guide to Pharmacology 1666
PubChem 128563
SureChEMBL SCHEMBL39147
ZINC ZINC000013607514
CONTENTS