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Compound Detail

CHEMBL350221

OXITRIPTAN
🧪 Phase III
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🧪 Phase III
N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL350221
Name OXITRIPTAN
Phase Phase III
Structure Type MOL
InChI Key LDCYZAJDBXYCGN-VIFPVBQESA-N
Therapeutic ✓ Yes

Known Names

5-hydroxy-l-tryptophan 5-hydroxytryptophan 5-hydroxytryptophan l-form 5-hydroxytryptophan, dl- Cincofarm Dl-5-htp Dl-5-hydroxytryptophan Dl-hydroxytryptophan Dl-oxitriptan Hydroxytryptophan L-5-htp L-5-hydroxytryptophan +12 more
7
Targets
12
Activities
2
Assay Types
0
PK Parameters
20
Publications
24
Known Names
5
Indications

Molecular Properties

220.2
MW (Da)
0.83
ALogP
3
HBA
4
HBD
99.3
PSA (Ų)
0.62
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -triptan

Extended Properties

Molecular Formula C11H12N2O3
MW 220.23
Aromatic Rings 2
Heavy Atoms 16
NP-Likeness 0.79

Indications

Depressive Disorder Sleep Wake Disorders Depressive Disorder, Major Obesity Spinal Cord Injuries

ATC Classification

N06AX01
oxitriptan
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

EC50 8 meas. best 9.74
Ki 4 meas. best 9.04

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2C
CHEMBL225
 EC50 9.74 9.7 0.2 2
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 9.04 8.89 0.9 2
5-hydroxytryptamine receptor 2B
CHEMBL1833
 EC50 9.0 8.945 1.0 2
5-hydroxytryptamine receptor 2A
CHEMBL224
 EC50 8.87 8.16 1.3 3
5-hydroxytryptamine receptor 7
CHEMBL3155
 Ki 8.67 8.67 2.1 1
5-hydroxytryptamine receptor 4
CHEMBL4317
 EC50 8.01 8.01 9.8 1
Serotonin 3 (5-HT3) receptor
CHEMBL2094116
 Ki 6.8 6.8 158.5 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2C EC50 = 0.18 nM 9.74 Agonist activity at recombinant human 5HT2C-INI receptor expressed in Flp-In-293... 26704965
5-hydroxytryptamine receptor 2C EC50 = 0.2188 nM 9.66 Agonist activity at recombinant human 5HT2C-INI receptor expressed in Flp-In-293... 26704965
5-hydroxytryptamine receptor 1A Ki = 0.91 nM 9.04 Displacement of [3H]-5-HT from human 5-HT1A receptor expressed in CHOK1 cells af... 25759032
5-hydroxytryptamine receptor 2B EC50 = 1.0 nM 9.0 Agonist activity at recombinant human 5HT2B receptor expressed in Flp-In-293 cel... 26704965
5-hydroxytryptamine receptor 2B EC50 = 1.288 nM 8.89 Agonist activity at recombinant human 5HT2B receptor expressed in Flp-In-293 cel... 26704965
5-hydroxytryptamine receptor 2A EC50 = 1.349 nM 8.87 Agonist activity at recombinant human 5HT2A receptor expressed in Flp-In-293 cel... 26704965
5-hydroxytryptamine receptor 1A Ki = 1.8 nM 8.74 Displacement of [3H]-8-OH-DPAT from 5-HT1A receptor (unknown origin) expressed i... 26227779
5-hydroxytryptamine receptor 2A EC50 = 1.9 nM 8.72 Agonist activity at recombinant human 5HT2A receptor expressed in Flp-In-293 cel... 26704965
5-hydroxytryptamine receptor 7 Ki = 2.12 nM 8.67 Displacement of [3H]-8-OH-DPAT from human 5-HT7 receptor expressed in CHOK1 cell... 25759032
5-hydroxytryptamine receptor 4 EC50 = 9.772 nM 8.01 Tested for its agonist potency against the 5-hydroxytryptamine 4 receptor locate... -
5-hydroxytryptamine receptor 2A EC50 = 130.0 nM 6.89 Agonist activity at 5-HT2A receptor (unknown origin) expressed in HEK293 cell me... 26227779
Serotonin 3 (5-HT3) receptor Ki = 158.49 nM 6.8 Tested for its binding affinity by measuring its ability to displace [3H]granise... -

Literature References

PubMed DOI Target Context # Activities
25815143 10.1021/ml500385d Indoleamine 2,3-dioxygenase 1 5
38888620 10.1021/acs.jnatprod.4c00118 Staphylococcus aureus 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
26704965 10.1021/acs.jmedchem.5b01153 5-hydroxytryptamine receptor 2A 2
26704965 10.1021/acs.jmedchem.5b01153 5-hydroxytryptamine receptor 2B 2
26704965 10.1021/acs.jmedchem.5b01153 5-hydroxytryptamine receptor 2C 2
25815143 10.1021/ml500385d Tryptophan 2,3-dioxygenase 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
19113967 10.1021/np800501m Tryprostatin B synthase ftmPT1 2
19113967 10.1021/np800501m Unchecked 2
- 10.1016/S0960-894X(01)81243-9 5-hydroxytryptamine receptor 4 2
26227779 10.1016/j.bmcl.2015.07.030 5-hydroxytryptamine receptor 2A 1
38888620 10.1021/acs.jnatprod.4c00118 Enterococcus faecium 1
25759032 10.1016/j.bmcl.2015.02.042 5-hydroxytryptamine receptor 7 1
25759032 10.1016/j.bmcl.2015.02.042 5-hydroxytryptamine receptor 1A 1
17417631 10.1038/nchembio873 Unchecked 1
- 10.1101/2020.04.21.054387 SARS-CoV-2 1

Data from ChEMBL 36 via Core Engine