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Compound Detail

CHEMBL537669

YOHIMBINE HYDROCHLORIDE
🧪 Phase III
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🧪 Phase III
COC(=O)[C@@H]1[C@H]2C[C@H]3c4[nH]c5ccccc5c4CCN3C[C@@H]2CC[C@@H]1O.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL537669
Name YOHIMBINE HYDROCHLORIDE
Phase Phase III
Structure Type MOL
InChI Key PIPZGJSEDRMUAW-VJDCAHTMSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL15245
Active Moiety CHEMBL15245

Known Names

NSC-19509 Prowess plain Yocon Yohimbine hcl Yohimbine hydrochloride
4
Targets
11
Activities
2
Assay Types
0
PK Parameters
18
Publications
5
Known Names
3
Indications

Molecular Properties

354.4
MW (Da)
2.65
ALogP
4
HBA
2
HBD
65.6
PSA (Ų)
0.77
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula C21H27ClN2O3
MW 390.91
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 1.17

Indications

Phobia, Social Depressive Disorder Tobacco Use Disorder

Activity Summary

IC50 8 meas. best 8.44
Ki 3 meas. best 8.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Alpha-2A adrenergic receptor
CHEMBL1867
 Ki 8.74 8.74 1.8 1
Alpha-2C adrenergic receptor
CHEMBL1916
 Ki 8.72 8.72 1.9 1
Alpha-2A adrenergic receptor
CHEMBL1867
 IC50 8.44 8.44 3.7 1
Alpha-2B adrenergic receptor
CHEMBL1942
 Ki 7.82 7.82 15.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
 IC50 7.57 7.57 27.1 1
Plasmodium falciparum
CHEMBL364
 IC50 5.7 5.4833 1995.3 6

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Alpha-2A adrenergic receptor Ki = 1.8 nM 8.74 Displacement of [3H]MK-912 from adrenergic alpha2A receptor in HT29 cells 17257841
Alpha-2C adrenergic receptor Ki = 1.9 nM 8.72 Displacement of [3H]MK912 from adrenergic Alpha-2C receptor in HepG2 cells 17257841
Alpha-2A adrenergic receptor IC50 = 3.67 nM 8.44 Displacement of [3H]MK9112 from human recombinant adrenergic alpha2A receptor ex... 19788200
Alpha-2B adrenergic receptor Ki = 15.0 nM 7.82 Displacement of [3H]MK912 from adrenergic alpha-2B receptor expressed in COS7 ce... 17257841
Alpha-2C adrenergic receptor IC50 = 27.1 nM 7.57 Displacement of radioligand from human adrenergic Alpha-2C receptor after 60 min... 19788200
Plasmodium falciparum IC50 = 1995.26 nM 5.7 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 1995.26 nM 5.7 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 3162.28 nM 5.5 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 3981.07 nM 5.4 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 3981.07 nM 5.4 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 6309.57 nM 5.2 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 6
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
20739103 10.1016/j.ejmech.2010.07.050 Unchecked 2
20739103 10.1016/j.ejmech.2010.07.050 Saccharomyces cerevisiae 2
23062825 10.1016/j.bmc.2012.09.040 Acetylcholinesterase 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
- 10.1101/2020.04.03.023846 SARS-CoV-2 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
23062825 10.1016/j.bmc.2012.09.040 Cholinesterase 1
17257841 10.1016/j.bmcl.2006.12.094 Alpha-2A adrenergic receptor 1
17417631 10.1038/nchembio873 Unchecked 1
19788200 10.1021/jm900458r Alpha-2C adrenergic receptor 1
19788200 10.1021/jm900458r Alpha-2A adrenergic receptor 1
17257841 10.1016/j.bmcl.2006.12.094 Alpha-2C adrenergic receptor 1
17257841 10.1016/j.bmcl.2006.12.094 Alpha-2B adrenergic receptor 1

Data from ChEMBL 36 via Core Engine