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Compound Detail

CHEMBL485832

GUANIDINONALTRINDOLE
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N=C(N)Nc1ccc2[nH]c3c(c2c1)C[C@@]1(O)[C@H]2Cc4ccc(O)c5c4[C@@]1(CCN2CC1CC1)[C@H]3O5
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL485832
Name GUANIDINONALTRINDOLE
Phase Preclinical
Structure Type MOL
InChI Key VLNHDKDBGWXJEE-GYHUNEDQSA-N
8
Targets
28
Activities
2
Assay Types
9
PK Parameters
20
Publications
0
Known Names

Molecular Properties

471.6
MW (Da)
2.88
ALogP
5
HBA
6
HBD
130.6
PSA (Ų)
0.26
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H29N5O3
MW 471.56
Aromatic Rings 3
Heavy Atoms 35
NP-Likeness 0.94

Activity Summary

Ki 25 meas. best 10.52
Kd 3 meas. best 10.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kappa-type opioid receptor
CHEMBL3614
 Ki 10.52 9.451 0.0 10
Kappa-type opioid receptor
CHEMBL237
 Kd 10.4 10.4 0.0 1
Mu-type opioid receptor
CHEMBL270
 Ki 10.05 8.16 0.1 7
Kappa-type opioid receptor
CHEMBL237
 Ki 9.82 9.77 0.1 2
Kappa-type opioid receptor
CHEMBL3952
 Ki 9.74 9.74 0.2 1
Delta-type opioid receptor
CHEMBL3222
 Ki 8.96 7.9667 1.1 3
Mu-type opioid receptor
CHEMBL233
 Kd 8.49 8.49 3.2 1
Delta-type opioid receptor
CHEMBL236
 Kd 7.81 7.81 15.5 1
Delta-type opioid receptor
CHEMBL269
 Ki 7.33 7.245 46.2 2

Pharmacokinetic Data

Parameter Value Units Species
Ke 0.14 nM Cavia porcellus
Ke 30.0 nM Cavia porcellus
Ke 115.0 nM -
Ke 0.16 nM Cavia porcellus
Ke 115.0 nM -
Ke 30.3 nM Cavia porcellus
Ke 0.2 nM Cavia porcellus
Ke 30.0 nM Cavia porcellus
Ke - - -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kappa-type opioid receptor Ki = 0.03 nM 10.52 Displacement of [3H]diprenorphine from k-Y312A-receptor expressed in HEK 293 cel... 11300867
Kappa-type opioid receptor Kd = 0.03981 nM 10.4 Antagonistic activity against human cloned kOpioid receptor kappa 1 using U69,59... 12825951
Kappa-type opioid receptor Ki = 0.06 nM 10.22 Mutant factor of the compound against mu-[K303E] with Opioid receptor kappa 1 fo... 9836606
Kappa-type opioid receptor Ki = 0.09 nM 10.05 Effect on binding affinity of mutational exchange of Glu297 in the Opioid recept... 9836606
Mu-type opioid receptor Ki = 0.09 nM 10.05 Displacement of [3H]- diprenorphine from mu-K303E-receptor expressed in HEK 293 ... 11300867
Kappa-type opioid receptor Ki = 0.14 nM 9.85 Binding affinity towards rat opioid receptor kappa 1 was determined using [3H]di... 11405645
Kappa-type opioid receptor Ki = 0.15 nM 9.82 Displacement of [125I]-IBNtxA from KOR-1 expressed in CHO cells 21621410
Kappa-type opioid receptor Ki = 0.18 nM 9.74 Displacement of [3H]diprenorphine from opioid receptor kappa 1 expressed in HEK ... 11300867
Kappa-type opioid receptor Ki = 0.18 nM 9.74 Inhibition of [3H]U-69593 binding to Opioid receptor kappa 1 of guinea pig brain 12825951
Kappa-type opioid receptor Ki = 0.18 nM 9.74 Binding affinity on HEK293 cells transiently transfected with plasmids encoding ... 10893314
Kappa-type opioid receptor Ki = 0.19 nM 9.72 Displacement of [125I]-IBNalA from KOR-1 expressed in CHO cells 21621410
Kappa-type opioid receptor Ki = 0.21 nM 9.68 Effect on binding to wild-type opioid receptor kappa 1 using [3H]diprenorphine i... 11405645
Mu-type opioid receptor Ki = 0.5 nM 9.3 Displacement of [3H]- diprenorphine from mu-W318A-receptor expressed in HEK 293 ... 11300867
Delta-type opioid receptor Ki = 1.1 nM 8.96 Displacement of [3H]- diprenorphine from delta-W284E-receptor expressed in HEK 2... 11300867
Mu-type opioid receptor Kd = 3.236 nM 8.49 Antagonistic activity against human cloned Opioid receptor mu 1 using DPDPE in [... 12825951
Kappa-type opioid receptor Ki = 3.93 nM 8.41 Effect on binding to kappa(Glu297Ala) opioid receptor, using [3H]diprenorphine i... 11405645
Kappa-type opioid receptor Ki = 3.9 nM 8.41 Displacement of [3H]diprenorphine from k-E297A-receptor expressed in HEK 293 cel... 11300867
Mu-type opioid receptor Ki = 9.23 nM 8.04 Effect on binding affinity of mutational exchange of Lys303 in the Opioid recept... 9836606
Kappa-type opioid receptor Ki = 12.9 nM 7.89 Mutant factor of the compound against kappa[E297K] with Opioid receptor kappa 1 ... 9836606
Delta-type opioid receptor Kd = 15.49 nM 7.81 Antagonistic activity against human cloned Opioid receptor delta 1 using DPDPE i... 12825951

Literature References

PubMed DOI Target Context # Activities
9836606 10.1021/jm9805182 Kappa-type opioid receptor 8
11405645 10.1021/jm010095v Kappa-type opioid receptor 5
10893314 10.1021/jm0000665 Delta-type opioid receptor 3
10893314 10.1021/jm0000665 Mu-type opioid receptor 3
11405645 10.1021/jm010095v Delta-type opioid receptor 3
11405645 10.1021/jm010095v Mu-type opioid receptor 3
11300867 10.1021/jm000381r Mu-type opioid receptor 3
10893314 10.1021/jm0000665 Kappa-type opioid receptor 3
11300867 10.1021/jm000381r Kappa-type opioid receptor 3
10893314 10.1021/jm0000665 Opioid receptors; delta & kappa 2
19217280 10.1016/j.bmcl.2008.12.093 Unchecked 2
21621410 10.1016/j.bmcl.2011.05.008 Kappa-type opioid receptor 2
24055076 10.1016/j.bmc.2013.08.042 Unchecked 2
12825951 10.1021/jm030094y Kappa-type opioid receptor 2
12825951 10.1021/jm030094y Delta-type opioid receptor 2
12825951 10.1021/jm030094y Mu-type opioid receptor 2
11300867 10.1021/jm000381r Delta-type opioid receptor 2
23721804 10.1016/j.bmcl.2013.05.027 Unchecked 2
9836606 10.1021/jm9805182 Mu-type opioid receptor 2
9836606 10.1021/jm9805182 Opioid receptors; delta & kappa 1

Data from ChEMBL 36 via Core Engine