DIHYDROERGOTAMINE

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Synonyms
Status
Molecule Category Free-form
ATC N02CA01
UNII 436O5HM03C
EPA CompTox DTXSID6045614

Structure

InChI Key LUZRJRNZXALNLM-JGRZULCMSA-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
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
Assay Description Organism Bioactivity Reference
Inhibition of specific [3H]-prazosin binding (0.2 nM) to rat brain membranes alpha-1 adrenergic receptor None 27.0 nM
Inhibition of specific [3H]clonidine binding (0.4 nM) to rat brain membranes alpha-2 adrenergic receptor None 3.7 nM
In vitro antagonist activity against (-)-phenylephrine or (-)-norepinephrine-induced alpha1-adrenoceptor-mediated vasoconstriction of rabbit isolated pulmonary artery. Oryctolagus cuniculus 28.18 nM
In vivo antagonist activity against (-)-phenylephrine-induced alpha-1 adrenergic receptor mediated vasoconstriction in pithed normotensive rats. Rattus norvegicus 208.93 nM
Antagonist activity against B-HT 933-induced alpha-2-adrenoceptor-mediated vasoconstriction in pithed normotensive rats Rattus norvegicus 56.23 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: [3H] 8-OH-DPAT) None 0.659 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: [3H] 8-OH-DPAT) None 0.377 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1B radioligand binding (ligand: [125I] Cyanopindolol) Rattus norvegicus 0.846 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1B radioligand binding (ligand: [125I] Cyanopindolol) Rattus norvegicus 0.384 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 7.955 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 2.273 nM
DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 5.028 nM DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 2.035 nM
DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 8.088 nM DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 4.477 nM
DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 29.0 nM DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 14.0 nM
DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 1.032 nM DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 0.387 nM
DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 3.867 nM DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 1.766 nM
DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 10.0 nM DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 1.51 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 6.804 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 4.33 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: [3H] Mesulergine) None 90.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: [3H] Mesulergine) None 47.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT4 radioligand binding (ligand: [3H] GR-113808) Cavia porcellus 940.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT4 radioligand binding (ligand: [3H] GR-113808) Cavia porcellus 157.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 3.201 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 1.486 nM
DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) None 8.88 nM DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) None 2.96 nM
DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 5.336 nM DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 1.812 nM
DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) Rattus norvegicus 2.503 nM DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) Rattus norvegicus 1.669 nM
Inhibition of human MATE1-mediated ASP+ uptake expressed in HEK293 cells at 20 uM after 1.5 mins by fluorescence assay Homo sapiens 72.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 6.01 %
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 -0.14 % 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 -0.14 %

Related Entries

Cross References

Resources Reference
ChEBI 4562
ChEMBL CHEMBL1732
DrugBank DB00320
DrugCentral 888
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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