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Compound Detail

CHEMBL1255837

DIHYDROERGOCRISTINE MESYLATE
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CC(C)[C@@]1(NC(=O)[C@@H]2C[C@@H]3c4cccc5[nH]cc(c45)C[C@H]3N(C)C2)O[C@@]2(O)[C@@H]3CCCN3C(=O)[C@H](Cc3ccccc3)N2C1=O.CS(=O)(=O)O

Basic Information

ChEMBL ID CHEMBL1255837
Name DIHYDROERGOCRISTINE MESYLATE
Phase Preclinical
Structure Type MOL
InChI Key SPXACGZWWVIDGR-SPZWACKZSA-N
Parent Compound CHEMBL601773
Active Moiety CHEMBL601773
25
Targets
52
Activities
3
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

611.7
MW (Da)
2.72
ALogP
6
HBA
3
HBD
118.2
PSA (Ų)
0.41
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C36H45N5O8S
MW 707.85
Aromatic Rings 3
Heavy Atoms 45
NP-Likeness 1.05

Activity Summary

IC50 30 meas. best 9.14
Ki 20 meas. best 9.38
EC50 2 meas. best 5.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 9.38 9.38 0.4 1
D(2) dopamine receptor
CHEMBL217
Ki 9.31 9.31 0.5 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 9.18 9.18 0.7 1
5-hydroxytryptamine receptor 1A
CHEMBL273
IC50 9.14 9.14 0.7 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 9.13 9.13 0.7 1
D(3) dopamine receptor
CHEMBL234
Ki 9.11 9.11 0.8 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 8.9 8.9 1.3 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 8.9 8.9 1.3 1
D(2) dopamine receptor
CHEMBL217
IC50 8.83 8.83 1.5 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 8.79 8.79 1.6 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 8.7 8.7 2.0 1
D(3) dopamine receptor
CHEMBL234
IC50 8.64 8.64 2.3 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 8.64 8.64 2.3 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 8.44 8.44 3.6 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 8.44 8.44 3.6 1
Unchecked
CHEMBL612545
Ki 8.44 7.06 3.6 2
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 8.38 8.38 4.2 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 8.37 8.37 4.2 1
Unchecked
CHEMBL612545
IC50 8.27 6.955 5.4 2
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 8.18 8.18 6.6 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 8.13 8.13 7.4 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 8.1 8.1 7.9 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 8.06 8.06 8.7 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
Ki 7.96 7.96 11.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 7.82 7.82 15.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 7.72 7.72 19.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
IC50 7.62 7.62 24.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 7.38 7.38 42.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.9 6.9 125.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 6.62 6.62 239.0 1
Plasmodium falciparum
CHEMBL364
IC50 6.5 6.0571 316.2 7
Mu-type opioid receptor
CHEMBL233
Ki 6.46 6.46 345.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 6.23 6.23 589.0 1
5-hydroxytryptamine receptor 4
CHEMBL5017
Ki 6.09 6.09 819.0 1
Mu-type opioid receptor
CHEMBL233
IC50 6.07 6.07 850.0 1
D(1A) dopamine receptor
CHEMBL2056
IC50 5.93 5.93 1179.0 1
Beta-3 adrenergic receptor
CHEMBL246
Ki 5.61 5.61 2481.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 5.52 5.52 3000.0 1
Cytochrome P450 2C9
CHEMBL3397
IC50 5.52 5.52 3000.0 1
Cytochrome P450 2C19
CHEMBL3622
IC50 5.52 5.52 3000.0 1
Beta-3 adrenergic receptor
CHEMBL246
IC50 5.48 5.48 3308.0 1
5-hydroxytryptamine receptor 4
CHEMBL5017
IC50 5.31 5.31 4912.0 1
Trypanosoma cruzi
CHEMBL368
EC50 5.3 5.3 5000.0 1
ADMET
CHEMBL612558
EC50 4.33 4.33 47000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 1A Ki = 0.412 nM 9.38 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ... -
D(2) dopamine receptor Ki = 0.491 nM 9.31 DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) -
Alpha-1A adrenergic receptor Ki = 0.656 nM 9.18 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
5-hydroxytryptamine receptor 1A IC50 = 0.722 nM 9.14 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ... -
Alpha-2A adrenergic receptor Ki = 0.747 nM 9.13 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
D(3) dopamine receptor Ki = 0.777 nM 9.11 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
Alpha-2C adrenergic receptor Ki = 1.257 nM 8.9 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
Alpha-1B adrenergic receptor Ki = 1.272 nM 8.9 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
D(2) dopamine receptor IC50 = 1.474 nM 8.83 DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) -
Alpha-1A adrenergic receptor IC50 = 1.62 nM 8.79 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-2A adrenergic receptor IC50 = 1.993 nM 8.7 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
Alpha-1B adrenergic receptor IC50 = 2.298 nM 8.64 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
D(3) dopamine receptor IC50 = 2.288 nM 8.64 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
Alpha-1D adrenergic receptor Ki = 3.622 nM 8.44 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-2B adrenergic receptor Ki = 3.606 nM 8.44 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Unchecked Ki = 3.619 nM 8.44 DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) -
5-hydroxytryptamine receptor 2B Ki = 4.201 nM 8.38 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2A Ki = 4.24 nM 8.37 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Unchecked IC50 = 5.428 nM 8.27 DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) -
5-hydroxytryptamine receptor 2B IC50 = 6.601 nM 8.18 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
17417631 10.1038/nchembio873 Unchecked 1
20547819 10.1128/aac.01777-09 ADMET 1
20547819 10.1128/aac.01777-09 Trypanosoma cruzi 1
20547819 10.1128/aac.01777-09 Unchecked 1
23062825 10.1016/j.bmc.2012.09.040 Acetylcholinesterase 1
23062825 10.1016/j.bmc.2012.09.040 Cholinesterase 1
29043803 10.1021/acs.jnatprod.6b01052 HL 1
- 10.1101/2020.04.21.054387 SARS-CoV-2 1

Data from ChEMBL 36 via Core Engine