DIHYDROERGOTAMINE MESYLATE

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Trade Names
Synonyms
Status
Molecule Category Salt-form
UNII 81AXN7R2QT
Parent Compound: DIHYDROERGOTAMINE

Structure

InChI Key ADYPXRFPBQGGAH-UMYZUSPBSA-N
Smiles 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.CS(=O)(=O)O
InChI
InChI=1S/C33H37N5O5.CH4O3S/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;1-5(2,3)4/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39);1H3,(H,2,3,4)/t21-,23-,25-,26+,27+,32-,33+;/m1./s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C34H41N5O8S
Molecular Weight 679.8
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

Bioactivity

Mechanism of Action Action Reference
Serotonin 1d (5-HT1d) receptor agonist AGONIST DailyMed
Protein: Serotonin 1d (5-HT1d) receptor
Description: 5-hydroxytryptamine receptor 1D
Organism : Homo sapiens
P28221 ENSG00000179546
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 10
Assay Description Organism Bioactivity Reference
Antiplasmodial activity against Plasmodium falciparum CDY harboring modified mdr1 protein after 72 hrs by SYBR green assay in presence of 0.8 uM P-gp inhibitor verapamil Plasmodium falciparum 22.0 nM
Antiplasmodial activity against Plasmodium falciparum SDD harboring modified mdr1 protein after 72 hrs by SYBR green assay in presence of 0.8 uM P-gp inhibitor verapamil Plasmodium falciparum 933.0 nM
Antiplasmodial activity against Plasmodium falciparum CDY harboring modified mdr1 protein after 72 hrs by SYBR green assay Plasmodium falciparum 42.0 nM
Antiplasmodial activity against Plasmodium falciparum SDD harboring modified mdr1 protein after 72 hrs by SYBR green assay Plasmodium falciparum 874.0 nM
Antiplasmodial activity against Plasmodium falciparum 3BA6 harboring modified mdr1 protein after 72 hrs by SYBR green assay Plasmodium falciparum 864.0 nM
Antiplasmodial activity against Plasmodium falciparum 7G8 ATCC 567 after 72 hrs by SYBR green assay Plasmodium falciparum 7G8 333.0 nM
Antiplasmodial activity against Plasmodium falciparum D10 ATCC 564 after 72 hrs by SYBR green assay Plasmodium falciparum D10 276.0 nM
Antiplasmodial activity against Plasmodium falciparum DIV30 after 72 hrs by SYBR green assay Plasmodium falciparum 184.0 nM
Antiplasmodial activity against Plasmodium falciparum DIV14 after 72 hrs by SYBR green assay Plasmodium falciparum 308.0 nM
Antiplasmodial activity against Plasmodium falciparum PC26 after 72 hrs by SYBR green assay Plasmodium falciparum 297.0 nM
Antiplasmodial activity against Plasmodium falciparum PC49 after 72 hrs by SYBR green assay Plasmodium falciparum 293.0 nM
Antiplasmodial activity against Plasmodium falciparum JCK after 72 hrs by SYBR green assay Plasmodium falciparum 895.0 nM
Antiplasmodial activity against Plasmodium falciparum PC15 after 72 hrs by SYBR green assay Plasmodium falciparum 410.0 nM
Antiplasmodial activity against Plasmodium falciparum JC3 after 72 hrs by SYBR green assay Plasmodium falciparum 128.0 nM
Antiplasmodial activity against Plasmodium falciparum JF6 after 72 hrs by SYBR green assay Plasmodium falciparum 159.1 nM
Antiplasmodial activity against Plasmodium falciparum JF11 after 72 hrs by SYBR green assay Plasmodium falciparum 157.0 nM
Antiplasmodial activity against Plasmodium falciparum XG10 after 72 hrs by SYBR green assay Plasmodium falciparum 205.4 nM
Antiplasmodial activity against Plasmodium falciparum KC2 after 72 hrs by SYBR green assay Plasmodium falciparum 183.8 nM
Antiplasmodial activity against Plasmodium falciparum WE2 after 72 hrs by SYBR green assay Plasmodium falciparum 179.9 nM
Antiplasmodial activity against Plasmodium falciparum DIV17 after 72 hrs by SYBR green assay Plasmodium falciparum 255.0 nM
Antiplasmodial activity against Plasmodium falciparum PAD after 72 hrs by SYBR green assay Plasmodium falciparum 267.0 nM
Antiplasmodial activity against Plasmodium falciparum DEV after 72 hrs by SYBR green assay Plasmodium falciparum 263.8 nM
Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR green assay Plasmodium falciparum 7G8 199.53 nM Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR green assay Plasmodium falciparum 7G8 371.0 nM
Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR green assay Plasmodium falciparum HB3 891.0 nM Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR green assay Plasmodium falciparum HB3 794.33 nM
Antiplasmodial activity against Plasmodium falciparum WF12 after 72 hrs by SYBR green assay Plasmodium falciparum 357.6 nM
Antiplasmodial activity against Plasmodium falciparum XF12 after 72 hrs by SYBR green assay Plasmodium falciparum 357.6 nM
Antiplasmodial activity against Plasmodium falciparum DAN after 72 hrs by SYBR green assay Plasmodium falciparum 343.8 nM
Antiplasmodial activity against Plasmodium falciparum JB8 after 72 hrs by SYBR green assay Plasmodium falciparum 302.8 nM
Antiplasmodial activity against Plasmodium falciparum WC4 after 72 hrs by SYBR green assay Plasmodium falciparum 279.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 27.06 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 10.07 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 7.54 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 3.35 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.07 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.07 %

Cross References

Resources Reference
ChEBI 59756
ChEMBL CHEMBL1200517
FDA SRS 81AXN7R2QT
Guide to Pharmacology 121
KEGG C07798
PubChem 71171
SureChEMBL SCHEMBL40843
ZINC ZINC03978005
CONTENTS