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Compound Detail

CHEMBL317956

DELTORPHIN C
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CC(C)[C@H](NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](C)NC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)N[C@H](C(=O)NCC(N)=O)C(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL317956
Name DELTORPHIN C
Phase Preclinical
Structure Type BOTH
InChI Key CJAORFIPPWIGPG-QXYJMILXSA-N
11
Targets
73
Activities
4
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

768.9
MW (Da)
-1.66
ALogP
10
HBA
10
HBD
301.2
PSA (Ų)
0.07
QED
2
Ro5 Violations
21
Rot. Bonds

Drug Information

Molecule Type Protein
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C37H52N8O10
MW 768.87
Aromatic Rings 2
Heavy Atoms 55
NP-Likeness 0.02

Activity Summary

IC50 40 meas. best 10.1
Ki 28 meas. best 9.82
EC50 3 meas. best 8.33
Kd 2 meas. best 9.76

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Delta-type opioid receptor
CHEMBL269
 IC50 10.1 9.3667 0.1 6
Delta-type opioid receptor
CHEMBL3222
 IC50 9.96 9.4891 0.1 11
Mus musculus
CHEMBL375
 IC50 9.85 9.68 0.1 3
Delta-type opioid receptor
CHEMBL269
 Ki 9.82 9.4309 0.1 11
Mus musculus
CHEMBL375
 Kd 9.76 8.63 0.2 2
Mu-type opioid receptor
CHEMBL2858
 IC50 9.47 9.47 0.3 1
Delta-type opioid receptor
CHEMBL3222
 Ki 9.1 9.1 0.8 1
Delta-type opioid receptor
CHEMBL236
 IC50 8.89 7.635 1.3 2
Delta-type opioid receptor
CHEMBL236
 Ki 8.76 8.76 1.7 1
Mu-type opioid receptor
CHEMBL4354
 IC50 8.54 6.1163 2.9 8
Delta-type opioid receptor
CHEMBL236
 EC50 8.33 8.33 4.7 1
Delta-type opioid receptor
CHEMBL3222
 EC50 7.9 7.9 12.6 1
Mu-type opioid receptor
CHEMBL270
 Ki 6.83 6.45 147.0 12
Mu-type opioid receptor
CHEMBL233
 IC50 6.65 6.65 225.0 1
Cavia porcellus
CHEMBL369
 IC50 6.38 6.145 420.0 2
Oryctolagus cuniculus
CHEMBL374
 IC50 6.29 6.29 510.0 1
Mu-type opioid receptor
CHEMBL4354
 Ki 6.17 6.17 677.0 1
Mu-type opioid receptor
CHEMBL233
 EC50 5.95 5.95 1130.0 1
Mu-type opioid receptor
CHEMBL270
 IC50 5.78 5.7067 1680.0 3
Mu-type opioid receptor
CHEMBL2858
 Ki 5.7 5.7 1980.0 1
Kappa-type opioid receptor
CHEMBL237
 IC50 5.13 5.13 7330.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 4.0 hr Mus musculus
T1/2 1.833 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Delta-type opioid receptor IC50 = 0.08 nM 10.1 Displacement of [3H][Ile5,6]deltorphin-2 from delta opioid receptor in Wistar ra... 19435668
Delta-type opioid receptor IC50 = 0.11 nM 9.96 Inhibitory activity against Mouse vas deferens smooth muscle -
Mus musculus IC50 = 0.14 nM 9.85 Concentration required to inhibit electrically induced twitch by 50% in mouse va... 1335080
Delta-type opioid receptor IC50 = 0.147 nM 9.83 Inhibition of electrically evoked contractions in mouse vas deferens 1331451
Delta-type opioid receptor Ki = 0.15 nM 9.82 Opioid receptor delta 1 binding affinity by displacement of radioligand [3H][D-P... 9288177
Delta-type opioid receptor Ki = 0.15 nM 9.82 Displacement of [3H]DPDPE (0.63 nM) from Opioid receptor delta 1 8576920
Delta-type opioid receptor Ki = 0.15 nM 9.82 Affinity was assessed using competitive binding assay labeled with [3H]DPDPE (6.... 9258365
Delta-type opioid receptor IC50 = 0.16 nM 9.8 Inhibitory concentration against delta opioid receptor of electrically induced s... 8289188
Delta-type opioid receptor IC50 = 0.17 nM 9.77 Functional bioactivity against delta opioid receptor in mouse vas deferens 16366592
Mus musculus Kd = 0.1738 nM 9.76 Delta or Mu antagonist activity tested in mouse vas deferens (MVD) along with N,... 11806723
Mus musculus IC50 = 0.2 nM 9.7 In vitro concentration required to inhibit electrically evoked twitch in isolate... 9986710
Delta-type opioid receptor Ki = 0.21 nM 9.68 Binding affinity at Opioid receptor delta 1 using rat brain receptor (P2 synapto... 11806723
Delta-type opioid receptor Ki = 0.21 nM 9.68 Inhibition of [3H]-DADLE binding to opioid receptor delta in P2 membrane prepara... 1849997
Delta-type opioid receptor Ki = 0.24 nM 9.62 Binding affinity against opioid receptor delta in rats by displacing [3H]DPDPE 1335080
Delta-type opioid receptor Ki = 0.24 nM 9.62 Displacement of [3H]deltorphin II from rat delta opioid receptor in brain P2 syn... 16366592
Delta-type opioid receptor Ki = 0.31 nM 9.51 Binding affinity was determined on delta [3H]DPDPE site in rat brain synaptosome... 8254604
Mus musculus IC50 = 0.32 nM 9.49 Evaluated for its ability to inhibit electrically induced contractions in the mo... -
Mu-type opioid receptor IC50 = 0.34 nM 9.47 Tested for inhibition of amplification of electrically induced twitch in mouse v... 8254604
Delta-type opioid receptor IC50 = 0.36 nM 9.44 In vitro inhibition of electrically induced smooth muscle contractions of mouse ... 8289187
Delta-type opioid receptor IC50 = 0.371 nM 9.43 Agonist activity at delta opioid receptor assessed as inhibition of electrically... 16942034

Literature References

PubMed DOI Target Context # Activities
8289187 10.1021/jm00027a017 Mu-type opioid receptor 4
1331451 10.1021/jm00099a025 Mu-type opioid receptor 4
1331451 10.1021/jm00099a025 Delta-type opioid receptor 4
9986710 10.1021/jm9810699 Mus musculus 4
8289187 10.1021/jm00027a017 Delta-type opioid receptor 4
11958984 10.1016/s0960-894x(02)00035-5 Mu-type opioid receptor 3
18207400 10.1016/j.bmcl.2008.01.009 Delta-type opioid receptor 3
11448220 10.1021/jm015532k Mu-type opioid receptor 3
11448220 10.1021/jm015532k Delta-type opioid receptor 3
11806723 10.1021/jm010449i Delta-type opioid receptor 2
8289187 10.1021/jm00027a017 Unchecked 2
11806723 10.1021/jm010449i Mus musculus 2
9258365 10.1021/jm9700530 Delta-type opioid receptor 2
9258365 10.1021/jm9700530 Mu-type opioid receptor 2
- 10.1016/S0960-894X(01)81195-1 Delta-type opioid receptor 2
- 10.1016/S0960-894X(01)81195-1 Mu-type opioid receptor 2
8254604 10.1021/jm00076a001 Mu-type opioid receptor 2
11958984 10.1016/s0960-894x(02)00035-5 Delta-type opioid receptor 2
8230106 10.1021/jm00073a020 Mu-type opioid receptor 2
8289187 10.1021/jm00027a017 Opioid receptors; mu & delta 2

Data from ChEMBL 36 via Core Engine