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Compound Detail

CHEMBL200199

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

Basic Information

ChEMBL ID CHEMBL200199
Name BIPHALIN
Phase Preclinical
Structure Type MOL
InChI Key DESSEGDLRYOPTJ-VRANXALZSA-N
11
Targets
89
Activities
3
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

909.0
MW (Da)
-1.62
ALogP
12
HBA
12
HBD
325.3
PSA (Ų)
0.04
QED
3
Ro5 Violations
22
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C46H56N10O10
MW 909.01
Aromatic Rings 4
Heavy Atoms 66
NP-Likeness -0.16

Activity Summary

IC50 37 meas. best 8.95
EC50 26 meas. best 9.0
Ki 26 meas. best 9.27

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 9.27 9.27 0.5 1
Mu-type opioid receptor
CHEMBL270
 Ki 9.1 8.8491 0.8 11
Delta-type opioid receptor
CHEMBL236
 EC50 9.0 8.9226 1.0 19
Mu-type opioid receptor
CHEMBL233
 EC50 9.0 9.0 1.0 1
Delta-type opioid receptor
CHEMBL236
 IC50 8.95 8.6825 1.1 4
Mu-type opioid receptor
CHEMBL233
 IC50 8.85 8.85 1.4 2
Unchecked
CHEMBL612545
 IC50 8.85 8.72 1.4 2
Delta-type opioid receptor
CHEMBL269
 Ki 8.59 8.29 2.6 3
Delta-type opioid receptor
CHEMBL236
 Ki 8.59 8.5588 2.6 8
Delta-type opioid receptor
CHEMBL3222
 IC50 8.57 8.2843 2.7 14
Mu-type opioid receptor
CHEMBL270
 EC50 8.22 8.07 6.0 2
Mu-type opioid receptor
CHEMBL270
 IC50 8.22 8.22 6.0 1
Cavia porcellus
CHEMBL369
 EC50 8.06 8.06 8.8 1
Mu-type opioid receptor
CHEMBL4354
 IC50 8.06 8.06 8.8 14
Mu-type opioid receptor
CHEMBL233
 Ki 7.92 7.92 12.0 1
Mus musculus
CHEMBL375
 EC50 7.57 7.57 27.0 1
Unchecked
CHEMBL612545
 EC50 7.12 7.12 75.4 1
Delta-type opioid receptor
CHEMBL3222
 EC50 7.04 7.04 90.5 1
Kappa-type opioid receptor
CHEMBL237
 Ki 6.57 6.57 270.0 1
Kappa-type opioid receptor
CHEMBL3614
 Ki 6.55 6.55 283.1 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.55 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.54 nM 9.27 Selectivity ratio, Ki for rat mu opioid receptor to Ki for human delta opioid re... 20560643
Mu-type opioid receptor Ki = 0.79 nM 9.1 Displacement of [3H]DAMGO from MOR in Wistar rat whole brain membranes after 45 ... 28835802
Delta-type opioid receptor EC50 = 1.0 nM 9.0 Agonist activity at human delta opioid receptor expressed in mouse HN9.10 cells ... 18821747
Delta-type opioid receptor EC50 = 1.0 nM 9.0 Binding affinity to DOR (unknown origin) 28835802
Mu-type opioid receptor EC50 = 1.0 nM 9.0 Binding affinity to MOR (unknown origin) 28835802
Delta-type opioid receptor EC50 = 1.1 nM 8.96 Agonist activity at human opioid delta receptor expressed in mouse HN9.10 cells ... 21366266
Delta-type opioid receptor EC50 = 1.1 nM 8.96 Agonist activity at human delta opioid receptor expressed in mouse HN9.10 cells ... 18821747
Delta-type opioid receptor EC50 = 1.1 nM 8.96 Agonist activity at human delta opioid receptor by [35S]GTP-gamma-S binding assa... 18266313
Delta-type opioid receptor EC50 = 1.1 nM 8.96 Agonist activity at human delta opioid receptor expressed in HN9.10 cells assess... 19762245
Delta-type opioid receptor EC50 = 1.1 nM 8.96 Agonist activity at human delta opioid receptor expressed in mouse HN9.10 cell m... 20560643
Delta-type opioid receptor EC50 = 1.1 nM 8.96 Agonist activity at human opioid delta receptor expressed in mouse HN9.10 cells ... 20617791
Delta-type opioid receptor EC50 = 1.1 nM 8.96 Activity at human delta opioid receptor expressed in CHO cells by [35S]GTP-gamma... 17201419
Delta-type opioid receptor EC50 = 1.1 nM 8.96 Inhibition of [35S]GTP-gamma-S binding to human delta opioid receptor expressed ... 16509592
Delta-type opioid receptor EC50 = 1.1 nM 8.96 Agonist activity at human delta opioid receptor expressed in HN9.10 cells assess... 17516639
Delta-type opioid receptor EC50 = 1.122 nM 8.95 Agonist activity at human opioid delta receptor expressed in mouse HN9.10 cells ... 20617791
Delta-type opioid receptor EC50 = 1.122 nM 8.95 Agonist activity at human delta opioid receptor expressed in HN9.10 cells assess... 17516639
Delta-type opioid receptor EC50 = 1.122 nM 8.95 Inhibition of [35S]GTP-gamma-S binding to human delta opioid receptor expressed ... 16509592
Delta-type opioid receptor EC50 = 1.122 nM 8.95 Agonist activity at human delta opioid receptor expressed in HN9.10 cells assess... 19762245
Delta-type opioid receptor EC50 = 1.122 nM 8.95 Agonist activity at human opioid delta receptor expressed in mouse HN9.10 cells ... 21366266
Delta-type opioid receptor IC50 = 1.122 nM 8.95 Activity at human delta opioid receptor expressed in CHO cells by [35S]GTP-gamma... 17201419

Literature References

PubMed DOI Target Context # Activities
21366266 10.1021/jm101023r Delta-type opioid receptor 5
18821747 10.1021/jm800389v Delta-type opioid receptor 5
18266313 10.1021/jm070332f Delta-type opioid receptor 5
17516639 10.1021/jm061369n Delta-type opioid receptor 5
19762245 10.1016/j.bmc.2009.08.035 Delta-type opioid receptor 5
20560643 10.1021/jm900473p Delta-type opioid receptor 5
23547584 10.1021/jm301456c Mus musculus 5
16275086 10.1016/j.bmcl.2005.09.080 Delta-type opioid receptor 4
16275086 10.1016/j.bmcl.2005.09.080 Mu-type opioid receptor 4
16509592 10.1021/jm050851n Delta-type opioid receptor 4
25221662 10.1021/ml500241n Delta-type opioid receptor 4
20617791 10.1021/jm100157m Delta-type opioid receptor 4
17201419 10.1021/jm061268p Delta-type opioid receptor 4
23623418 10.1016/j.bmcl.2013.03.065 Mu-type opioid receptor 4
25221662 10.1021/ml500241n Mu-type opioid receptor 4
23623418 10.1016/j.bmcl.2013.03.065 Delta-type opioid receptor 4
31834798 10.1021/acs.jmedchem.9b01963 Mus musculus 3
28835802 10.1021/acsmedchemlett.7b00210 Unchecked 3
25221662 10.1021/ml500241n Kappa-type opioid receptor 3
30996778 10.1021/acsmedchemlett.8b00495 Mus musculus 2

Data from ChEMBL 36 via Core Engine