DIHYDROERGOTAMINE

Search structure
Synonyms:
Status: Approved (1946)
Entry Type: Small molecule
Molecule Category: Parent
ATC: N02CA01
UNII: 436O5HM03C

Structure
InChI Key LUZRJRNZXALNLM-JGRZULCMSA-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[C@@H]2c3cccc4[nH]cc(c34)C[C@H]21
InChI
InChI=1S/C33H37N5O5/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/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39)/t21-,23-,25-,26+,27+,32-,33+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C33H37N5O5
Molecular Weight 583.69
AlogP 2.08
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
- 2999 - - -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Cholecystokinin receptor
- 23000 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- 27 209 - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 49900 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- 12600 - - 72

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Migraine with Aura 3 D020325 ClinicalTrials
Migraine without Aura 3 D020326 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt

Cross References

Resources Reference
CAS NUMBER 511-12-6
ChEBI 4562
ChEMBL CHEMBL1732
DrugBank DB00320
DrugCentral 888
EPA CompTox DTXSID6045614
FDA SRS 436O5HM03C
Human Metabolome Database HMDB0014465
Guide to Pharmacology 121
KEGG C07798
PDB 2GM
PharmGKB PA164743028
PubChem 10531
SureChEMBL SCHEMBL44931
ZINC ZINC000003978005
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