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Compound Detail

CHEMBL445332

SALVINORIN A
Phase I
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Phase I
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
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL445332
Name SALVINORIN A
Phase Phase I
Structure Type MOL
InChI Key OBSYBRPAKCASQB-AGQYDFLVSA-N

Known Names

(-)-salvinorin a Divinorin a Salvinorin Salvinorin a
8
Targets
104
Activities
2
Assay Types
5
PK Parameters
20
Publications
4
Known Names

Molecular Properties

432.5
MW (Da)
3.00
ALogP
8
HBA
0
HBD
109.1
PSA (Ų)
0.53
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product Chemical Probe
USAN Stem sal-; -vin-

Extended Properties

Molecular Formula C23H28O8
MW 432.47
Aromatic Rings 1
Heavy Atoms 31
NP-Likeness 2.98

Activity Summary

Ki 59 meas. best 9.12
EC50 45 meas. best 10.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kappa-type opioid receptor
CHEMBL237
 EC50 10.82 8.602 0.0 40
Kappa-type opioid receptor
CHEMBL237
 Ki 9.12 8.4674 0.8 27
Kappa-type opioid receptor
CHEMBL3614
 Ki 9.12 7.6423 0.8 22
Kappa-type opioid receptor
CHEMBL3952
 Ki 8.37 8.37 4.3 1
Kappa-type opioid receptor
CHEMBL4329
 EC50 8.16 7.57 6.9 2
Kappa-type opioid receptor
CHEMBL4329
 Ki 7.73 7.73 18.7 1
Rattus norvegicus
CHEMBL376
 EC50 7.34 7.34 46.0 1
Unchecked
CHEMBL612545
 Ki 6.34 6.31 458.0 2
Mu-type opioid receptor
CHEMBL233
 Ki 5.86 5.61 1370.0 2
Mu-type opioid receptor
CHEMBL233
 EC50 5.54 5.54 2860.0 1
Delta-type opioid receptor
CHEMBL236
 Ki 5.4 5.28 3990.0 4

Pharmacokinetic Data

Parameter Value Units Species
Ke - - Homo sapiens
Ke - - Homo sapiens
Ke - - Homo sapiens
Ke 5000.0 nM Homo sapiens
Ke 5000.0 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kappa-type opioid receptor EC50 = 0.015 nM 10.82 Agonist activity at human KOR expressed in HEK293T cells assessed as inhibition ... 30543421
Kappa-type opioid receptor EC50 = 0.03 nM 10.52 Agonist activity at human KOR expressed in CHO cells assessed as inhibition of f... 25426797
Kappa-type opioid receptor EC50 = 0.03 nM 10.52 Agonist activity at human KOR expressed in CHOK1 cells assessed as inhibition of... 33479684
Kappa-type opioid receptor EC50 = 0.042 nM 10.38 Agonist activity at human kappa-type opioid receptor expressed in CHO-K1 cells a... 28718638
Kappa-type opioid receptor EC50 = 0.05643 nM 10.25 Agonist activity at KOR (unknown origin) by Glo sensor assay 28288109
Kappa-type opioid receptor EC50 = 0.2 nM 9.7 Agonist activity at kappa opioid receptor expressed in HEK293 cells by [35S]GTPg... 21115248
Kappa-type opioid receptor EC50 = 0.2 nM 9.7 Agonist activity at wild type human KOR receptor expressed in CHO cells assessed... 36179400
Kappa-type opioid receptor EC50 = 0.21 nM 9.68 Agonist activity at human kappa-type opioid receptor expressed in CHO-K1 cells a... 28376298
Kappa-type opioid receptor EC50 = 0.36 nM 9.44 Inhibition of human kappa opioid receptor expressed in HEK293T cells assessed as... 25193297
Kappa-type opioid receptor Ki = 0.75 nM 9.12 Displacement of [3H]U-69593 from rat cloned KOR 17303418
Kappa-type opioid receptor Ki = 0.75 nM 9.12 Displacement of [3H]U69593 from kappa opioid receptor expressed in HEK293 cells 21115248
Kappa-type opioid receptor Ki = 0.8 nM 9.1 Displacement of [3H]U69593 from kappa opioid receptor expressed in HEK293 cells ... 19683449
Kappa-type opioid receptor EC50 = 0.81 nM 9.09 Agonist activity at human kappa opioid receptor-Galpha-16 fusion protein express... 16441078
Kappa-type opioid receptor EC50 = 1.24 nM 8.91 Agonist activity at human kappa opioid receptor assessed as inhibition of Galpha... 17904842
Kappa-type opioid receptor Ki = 1.3 nM 8.89 Inhibition of [3H]diprenorphine binding to human Opioid receptor kappa 1 express... 15869877
Kappa-type opioid receptor Ki = 1.3 nM 8.89 Inhibition of [3H]diprenorphine binding to human KOR expressed in CHO cells 16777411
Kappa-type opioid receptor Ki = 1.3 nM 8.89 Displacement of [3H]diprenorphine binding from human kappa opioid receptor expre... 16945525
Kappa-type opioid receptor Ki = 1.3 nM 8.89 Displacement of [3H]diprenorphine from human kappa opioid receptor expressed in ... 26330078
Kappa-type opioid receptor EC50 = 1.7 nM 8.77 Agonist activity at human kappa opioid receptor expressed CHO cells co-expressin... 25075762
Kappa-type opioid receptor EC50 = 1.8 nM 8.74 Agonist activity at human kappa opioid receptor expressed in CHO cells assessed ... 17981041

Literature References

PubMed DOI Target Context # Activities
18293909 10.1021/jm701040v Unchecked 21
18293909 10.1021/jm701040v Kappa-type opioid receptor 20
36179400 10.1016/j.ejmech.2022.114785 Kappa-type opioid receptor 9
33479684 10.1039/d0md00104j Mu-type opioid receptor 8
28376298 10.1021/acs.jmedchem.7b00148 Mus musculus 8
22204910 10.1016/j.bmcl.2011.11.128 Kappa-type opioid receptor 6
16777411 10.1016/j.bmcl.2006.05.093 Kappa-type opioid receptor 6
17303418 10.1016/j.bmcl.2007.01.100 Kappa-type opioid receptor 6
16441078 10.1021/np050398i Kappa-type opioid receptor 6
39088801 10.1021/acs.jmedchem.4c00590 Kappa-type opioid receptor 5
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 5
22464684 10.1016/j.bmc.2012.02.040 Kappa-type opioid receptor 5
16033256 10.1021/jm048963m Mus musculus 5
16033256 10.1021/jm048963m Delta-type opioid receptor 4
16033256 10.1021/jm048963m Mu-type opioid receptor 4
18380425 10.1021/jm701162g Unchecked 4
18380425 10.1021/jm701162g Kappa-type opioid receptor 4
26330078 10.1016/j.bmcl.2015.06.092 Kappa-type opioid receptor 4
18380425 10.1021/jm701162g Mu-type opioid receptor 4
16033256 10.1021/jm048963m Kappa-type opioid receptor 4

Data from ChEMBL 36 via Core Engine