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Compound Detail

CHEMBL6640

TRYPTAMINE
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NCCc1c[nH]c2ccccc12

Basic Information

ChEMBL ID CHEMBL6640
Name TRYPTAMINE
Phase Preclinical
Structure Type MOL
InChI Key APJYDQYYACXCRM-UHFFFAOYSA-N
22
Targets
35
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

160.2
MW (Da)
1.67
ALogP
1
HBA
2
HBD
41.8
PSA (Ų)
0.69
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C10H12N2
MW 160.22
Aromatic Rings 2
Heavy Atoms 12
NP-Likeness 0.05

Activity Summary

Ki 18 meas. best 7.64
EC50 7 meas. best 8.13
IC50 7 meas. best 6.11
Kd 3 meas. best 6.27

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL224
EC50 8.13 8.13 7.4 1
5-hydroxytryptamine receptor 1D
CHEMBL1983
Ki 7.64 7.425 23.0 2
Sodium-dependent serotonin transporter
CHEMBL313
EC50 7.49 7.49 32.6 1
5-hydroxytryptamine receptor 1B
CHEMBL1898
Ki 7.44 7.44 36.0 1
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
Ki 7.3 6.42 50.0 2
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 7.3 7.3 50.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 7.16 6.955 70.0 2
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 6.8 6.8 158.5 1
Sodium-dependent dopamine transporter
CHEMBL338
EC50 6.79 6.79 164.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 6.77 6.77 169.8 2
Trace amine-associated receptor 1
CHEMBL3833
EC50 6.51 6.51 310.0 1
5-hydroxytryptamine receptor 2B
CHEMBL323
Kd 6.27 6.27 537.0 1
Norepinephrine transporter
CHEMBL304
EC50 6.14 6.14 716.0 1
Myeloperoxidase
CHEMBL2439
IC50 6.11 6.11 770.0 1
Cytochrome P450 2A6
CHEMBL5282
Ki 5.77 5.77 1700.0 1
Trace amine-associated receptor 1
CHEMBL5857
EC50 5.66 5.66 2210.0 1
Cytochrome P450 2A6
CHEMBL5282
Kd 5.64 5.64 2300.0 1
Cytochrome P450 2A13
CHEMBL3542436
Kd 5.28 5.28 5200.0 1
Unchecked
CHEMBL612545
Ki 5.27 5.27 5400.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.22 4.9 6000.0 3
5-hydroxytryptamine receptor 1B
CHEMBL3459
Ki 4.99 4.99 10200.0 1
Cathepsin K
CHEMBL268
IC50 4.82 4.82 15000.0 1
Cytochrome P450 2A13
CHEMBL3542436
Ki 4.8 4.8 16000.0 1
Adrenergic receptor alpha-2
CHEMBL2093864
Ki 4.72 4.72 19000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A EC50 = 7.36 nM 8.13 Agonist activity at 5HT2A receptor (unknown origin) by cell based calcium mobili... 25193229
5-hydroxytryptamine receptor 1D Ki = 23.0 nM 7.64 Binding affinity towards 5-hydroxytryptamine 1D receptor was determined in calf ... 8568822
Sodium-dependent serotonin transporter EC50 = 32.6 nM 7.49 Induction of 5-HTT-mediated 5-HT release in rat brain synaptosomes by [3H]5-HT r... 25193229
5-hydroxytryptamine receptor 1B Ki = 36.0 nM 7.44 Displacement of [3H]-5-HT from human 5-hydroxytryptamine 1D receptor beta 8568822
5-hydroxytryptamine receptor 2C Ki = 50.0 nM 7.3 Evaluated for the binding affinity to porcine choroid plexus at 5-hydroxytryptam... 3543362
Serotonin 2 (5-HT2) receptor Ki = 50.0 nM 7.3 Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 receptor bin... 3543362
5-hydroxytryptamine receptor 1D Ki = 61.0 nM 7.21 In vitro affinity human cloned 5-hydroxytryptamine 1D receptor alpha by [3H]5-HT... 8568822
5-hydroxytryptamine receptor 6 Ki = 70.0 nM 7.16 Binding affinity to Homo sapiens (human) 5-HT6 receptor -
5-hydroxytryptamine receptor 7 Ki = 158.49 nM 6.8 Displacement of [3H]5-HT from recombinant human 5-HT7 receptor expressed in Afri... 31581003
Sodium-dependent dopamine transporter EC50 = 164.0 nM 6.79 Induction of DAT-mediated dopamine release in rat brain synaptosomes by [3H]DA r... 25193229
5-hydroxytryptamine receptor 1A Ki = 169.82 nM 6.77 Binding affinity of a compound to rat brain 5-hydroxytryptamine 1A (serotonin) r... 8568799
5-hydroxytryptamine receptor 1A Ki = 170.0 nM 6.77 Evaluated for the binding affinity to hippocampus striatal membranes at 5-hydrox... 3543362
5-hydroxytryptamine receptor 6 Ki = 180.0 nM 6.75 Binding affinity for human 5-hydroxytryptamine 6 receptor expressed in HEK 293 h... 10715164
Trace amine-associated receptor 1 EC50 = 310.0 nM 6.51 Agonist activity at rat N-terminal FLAG-tagged TAAR1 expressed in HEK293 cells a... 28244748
5-hydroxytryptamine receptor 2B Kd = 537.03 nM 6.27 The binding affinity to 5-hydroxytryptamine 2B receptor of rat fundus 7086824
Norepinephrine transporter EC50 = 716.0 nM 6.14 Induction of NET-mediated norepinephrine release in rat brain synaptosomes by [3... 25193229
Myeloperoxidase IC50 = 770.0 nM 6.11 Inhibition of human recombinant MPO-mediated taurine chlorination after 5 mins b... 23581551
Cytochrome P450 2A6 Ki = 1700.0 nM 5.77 Competitive inhibition of CYP2A6 (unknown origin) 22696418
Trace amine-associated receptor 1 EC50 = 2210.0 nM 5.66 Agonist activity at recombinant human TAAR1 expressed in CHO-K1 cells assessed a... 35047111
Cytochrome P450 2A6 Kd = 2300.0 nM 5.64 Binding affinity to CYP2A6 (unknown origin) assessed as type 2 interaction as in... 22696418

Literature References

PubMed DOI Target Context # Activities
20727623 10.1016/j.ejmech.2010.07.059 NON-PROTEIN TARGET 7
627999 10.1021/jm00201a003 Mus musculus 7
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
30660829 10.1016/j.ejmech.2019.01.012 Candida albicans 3
25815143 10.1021/ml500385d Indoleamine 2,3-dioxygenase 1 3
22823278 10.1021/jf302038a Plenodomus lingam 3
8568822 10.1021/jm950498t 5-hydroxytryptamine receptor 1D 3
35047111 10.1021/acsmedchemlett.1c00527 Trace amine-associated receptor 1 2
19640715 10.1016/j.bmcl.2009.07.082 Unchecked 2
19113967 10.1021/np800501m Tryprostatin B synthase ftmPT1 2
19113967 10.1021/np800501m Unchecked 2
22696418 10.1124/dmd.112.045161 Cytochrome P450 2A13 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
7658443 10.1021/jm00018a016 5-hydroxytryptamine receptor 1D 2
25193229 10.1016/j.bmcl.2014.07.062 5-hydroxytryptamine receptor 2A 2
27765507 10.1016/j.bmcl.2016.10.004 Escherichia coli 2
3543362 10.1021/jm00384a001 Serotonin 2 (5-HT2) receptor 2
22696418 10.1124/dmd.112.045161 Cytochrome P450 2A6 2
22696418 10.1124/dmd.112.045161 ADMET 2
39013034 10.1021/acs.jmedchem.4c00570 Solute carrier family 2, facilitated glucose transporter member 4 1

Data from ChEMBL 36 via Core Engine