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Compound Detail

CHEMBL1403281

ERGOCRYPTINE
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CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](NC(=O)[C@@H]3C=C4c5cccc6[nH]cc(c56)C[C@H]4N(C)C3)(C(C)C)C(=O)N12

Basic Information

ChEMBL ID CHEMBL1403281
Name ERGOCRYPTINE
Phase Preclinical
Structure Type MOL
InChI Key YDOTUXAWKBPQJW-NSLWYYNWSA-N
23
Targets
42
Activities
2
Assay Types
0
PK Parameters
6
Publications
0
Known Names

Molecular Properties

575.7
MW (Da)
2.43
ALogP
6
HBA
3
HBD
118.2
PSA (Ų)
0.50
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C32H41N5O5
MW 575.71
Aromatic Rings 2
Heavy Atoms 42
NP-Likeness 1.30

Activity Summary

Ki 22 meas. best 9.7
IC50 20 meas. best 9.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(3) dopamine receptor
CHEMBL234
Ki 9.7 9.7 0.2 1
D(3) dopamine receptor
CHEMBL234
IC50 9.23 9.23 0.6 1
D(2) dopamine receptor
CHEMBL217
Ki 9.19 9.19 0.7 1
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 8.82 8.82 1.5 1
D(2) dopamine receptor
CHEMBL217
IC50 8.71 8.71 1.9 1
Unchecked
CHEMBL612545
Ki 8.66 8.66 2.2 1
5-hydroxytryptamine receptor 1A
CHEMBL273
IC50 8.58 8.58 2.6 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 8.53 8.53 3.0 1
Unchecked
CHEMBL612545
IC50 8.48 8.48 3.3 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 8.37 8.37 4.3 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
Ki 8.3 8.3 5.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 8.26 8.26 5.5 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 8.12 8.12 7.6 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 8.1 8.1 7.9 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 8.1 8.1 7.9 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
IC50 8.09 8.09 8.2 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 8.09 8.09 8.2 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 7.96 7.96 11.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 7.92 7.92 12.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 7.89 7.89 13.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 7.85 7.85 14.0 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 7.85 7.85 14.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 7.8 7.8 16.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 7.62 7.62 24.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 7.58 7.58 26.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 7.42 7.42 38.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 7.33 7.33 47.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 7.32 7.32 48.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 7.11 7.11 77.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 6.83 6.83 147.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 6.7 6.7 202.0 1
D(1A) dopamine receptor
CHEMBL2056
IC50 6.39 6.39 403.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 6.22 6.22 600.0 1
Mu-type opioid receptor
CHEMBL233
Ki 6.01 6.01 985.0 1
Beta-3 adrenergic receptor
CHEMBL246
Ki 5.73 5.73 1872.0 1
Mu-type opioid receptor
CHEMBL233
IC50 5.62 5.62 2427.0 1
Beta-3 adrenergic receptor
CHEMBL246
IC50 5.6 5.6 2496.0 1
Cytochrome P450 2C9
CHEMBL3397
IC50 5.22 5.22 6000.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
Ki 5.19 5.05 6430.0 2
ATP-dependent translocase ABCB1
CHEMBL3467
Ki 4.57 4.57 26900.0 1
ATP-dependent translocase ABCB1
CHEMBL2573
Ki 4.36 4.36 43500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(3) dopamine receptor Ki = 0.2 nM 9.7 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
D(3) dopamine receptor IC50 = 0.589 nM 9.23 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
D(2) dopamine receptor Ki = 0.65 nM 9.19 DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) -
5-hydroxytryptamine receptor 1A Ki = 1.503 nM 8.82 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ... -
D(2) dopamine receptor IC50 = 1.95 nM 8.71 DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) -
Unchecked Ki = 2.186 nM 8.66 DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) -
5-hydroxytryptamine receptor 1A IC50 = 2.631 nM 8.58 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ... -
Alpha-2A adrenergic receptor Ki = 2.98 nM 8.53 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
Unchecked IC50 = 3.279 nM 8.48 DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) -
Alpha-1A adrenergic receptor Ki = 4.279 nM 8.37 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
5-hydroxytryptamine receptor 1B Ki = 5.021 nM 8.3 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1B radioligand binding (ligand: ... -
Alpha-2C adrenergic receptor Ki = 5.484 nM 8.26 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
5-hydroxytryptamine receptor 6 Ki = 7.559 nM 8.12 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [... -
Alpha-1B adrenergic receptor Ki = 7.938 nM 8.1 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-2A adrenergic receptor IC50 = 7.946 nM 8.1 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
5-hydroxytryptamine receptor 2B Ki = 8.217 nM 8.09 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 1B IC50 = 8.199 nM 8.09 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1B radioligand binding (ligand: ... -
Alpha-1A adrenergic receptor IC50 = 11.0 nM 7.96 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-2B adrenergic receptor Ki = 12.0 nM 7.92 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
5-hydroxytryptamine receptor 2B IC50 = 13.0 nM 7.89 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -

Literature References

PubMed DOI Target Context # Activities
11961113 10.1124/mol.61.5.964 ATP-dependent translocase ABCB1 2
12235267 10.1124/jpet.102.037549 ATP-dependent translocase ABCB1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.1016/S0960-894X(00)80644-7 Cholecystokinin receptor type A 1
- 10.1016/S0960-894X(00)80644-7 Gastrin/cholecystokinin type B receptor 1
37938154 10.1021/acs.jnatprod.3c00661 20S proteasome 1

Data from ChEMBL 36 via Core Engine