ERGOTAMINE

Search structure
Synonyms:
Status: Approved (1948)
Entry Type: Small molecule
Molecule Category: Parent
ATC: N02CA02
UNII: PR834Q503T

Structure
InChI Key XCGSFFUVFURLIX-VFGNJEKYSA-N
Smile CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](Cc4ccccc4)N3C2=O)C=C2c3cccc4[nH]cc(c34)C[C@H]21
InChI
InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C33H35N5O5
Molecular Weight 581.67
AlogP 1.99
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 4.0
Polar Surface Area 118.21
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 43.0

Pharmacology

Primary Target
5-HT1D receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 1000 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 5 Cytochrome P450 family 5A Cytochrome P450 5A1
- 3064 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Src family
- 3160 - - -
Enzyme
- 1000 - - -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Cholecystokinin receptor
- 17000 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- 12 - 0.796 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- 1728 - 1.433 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
7.3-7.943 0.201 - 0.8-6 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 16.7
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- - - 14250-98900 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hypotension, Orthostatic 1 D007024 ClinicalTrials

Related Entries

Scaffolds

Salt

Cross References

Resources Reference
CAS NUMBER 113-15-5
ChEBI 64318
ChEMBL CHEMBL442
DrugBank DB00696
DrugCentral 1043
EPA CompTox DTXSID9043774
FDA SRS PR834Q503T
Human Metabolome Database HMDB14834
Guide to Pharmacology 149
PDB ERM
PharmGKB PA164747651
PubChem 8223
SureChEMBL SCHEMBL1483
ZINC ZINC000052955754
CONTENTS