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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2019-01-11 19:35:38 UTC
HMDB IDHMDB0015383
Secondary Accession Numbers
  • HMDB15383
Metabolite Identification
Common NameErgonovine
DescriptionErgonovine is only found in individuals that have used or taken this drug. It is an ergot alkaloid with uterine and vascular smooth muscle contractile properties. [PubChem]Ergonovine directly stimulates the uterine muscle to increase force and frequency of contractions. With usual doses, these contractions precede periods of relaxation; with larger doses, basal uterine tone is elevated and these relaxation periods will be decreased. Contraction of the uterine wall around bleeding vessels at the placental site produces hemostasis. Ergonovine also induces cervical contractions. The sensitivity of the uterus to the oxytocic effect is much greater toward the end of pregnancy. The oxytocic actions of ergonovine are greater than its vascular effects. Ergonovine, like other ergot alkaloids, produces arterial vasoconstriction by stimulation of alpha-adrenergic and serotonin receptors and inhibition of endothelial-derived relaxation factor release. It is a less potent vasoconstrictor than ergotamine. As a diagnostic aid (coronary vasospasm), ergonovine causes vasoconstriction of coronary arteries.
Structure
Data?1547235338
Synonyms
ValueSource
(6AR,9R)-7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-FG]quinoline-9-carboxylic acid ((S)-2-hydroxy-1-methyl-ethyl)-amideChEBI
9,10-didehydro-N-(2-Hydroxy-1-methylethyl)-6-methylergoline-8beta(S)-carboxamideChEBI
9,10-didehydro-N-(alpha-(Hydroxymethyl)ethyl)-6-methylergoline-8-beta-carboxamideChEBI
[8beta(S)]-9,10-didehydro-N-(2-Hydroxy-1-methylethyl)-6-methylergoline-8-carboxamideChEBI
D-Lysergic acid 1-hydroxymethylethylamideChEBI
D-Lysergic acid-L-propanolamideChEBI
ErgobasineChEBI
ErgometrinaChEBI
ErgometrinumChEBI
ErgotocineChEBI
MargonovineChEBI
N-(2-Hydroxy-1-methylethyl)-D-(+)-lysergamideChEBI
N-(alpha-(Hydroxymethyl)ethyl)-D-lysergamideChEBI
(6AR,9R)-7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-FG]quinoline-9-carboxylate ((S)-2-hydroxy-1-methyl-ethyl)-amideGenerator
9,10-didehydro-N-(2-Hydroxy-1-methylethyl)-6-methylergoline-8b(S)-carboxamideGenerator
9,10-didehydro-N-(2-Hydroxy-1-methylethyl)-6-methylergoline-8β(S)-carboxamideGenerator
9,10-didehydro-N-(a-(Hydroxymethyl)ethyl)-6-methylergoline-8-b-carboxamideGenerator
9,10-didehydro-N-(α-(hydroxymethyl)ethyl)-6-methylergoline-8-β-carboxamideGenerator
[8b(S)]-9,10-didehydro-N-(2-Hydroxy-1-methylethyl)-6-methylergoline-8-carboxamideGenerator
[8β(S)]-9,10-didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8-carboxamideGenerator
D-Lysergate 1-hydroxymethylethylamideGenerator
D-Lysergate-L-propanolamideGenerator
N-(a-(Hydroxymethyl)ethyl)-D-lysergamideGenerator
N-(α-(hydroxymethyl)ethyl)-D-lysergamideGenerator
ErgometrineHMDB
Ergotrate maleateHMDB
Bedford brand OF ergonovine maleateMeSH
ErgobasinMeSH
ErgometrinMeSH
ErgotrateMeSH
Ergometrine maleateMeSH
Ergonovine maleateMeSH
Chemical FormulaC19H23N3O2
Average Molecular Weight325.4048
Monoisotopic Molecular Weight325.179026995
IUPAC Name(4R,7R)-N-[(2S)-1-hydroxypropan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
Traditional Nameergonovine
CAS Registry Number60-79-7
SMILES
[H][C@@]12CC3=CNC4=CC=CC(=C34)C1=C[C@H](CN2C)C(=O)N[C@@H](C)CO
InChI Identifier
InChI=1S/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11-,13+,17+/m0/s1
InChI KeyWVVSZNPYNCNODU-XTQGRXLLSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassErgoline and derivatives
Sub ClassLysergic acids and derivatives
Direct ParentLysergamides
Alternative Parents
Substituents
  • Lysergic acid amide
  • Indoloquinoline
  • Benzoquinoline
  • Pyrroloquinoline
  • Quinoline-3-carboxamide
  • Quinoline
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Isoindole or derivatives
  • Aralkylamine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Primary alcohol
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point162 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.32 g/LNot Available
LogP0.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.32 g/LALOGPS
logP1.53ALOGPS
logP1.07ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)15ChemAxon
pKa (Strongest Basic)7.93ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area68.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.05 m³·mol⁻¹ChemAxon
Polarizability36.54 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-3931000000-4bdb2fafa3f7edc31959View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006t-3941000000-efd4dcb7883cfc33a6d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-1029000000-c07ebacb47f673bb1d1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-2093000000-ac375307cfa93e46e2b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-3930000000-6800151137f550b0b24fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0029000000-87d6fc7041cc0a8ae488View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-4189000000-1718640f639f14c8ffbcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9270000000-c5c258e619a7caf0d202View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01253 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01253 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01253
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001722
Chemspider ID391970
KEGG Compound IDC07543
BioCyc IDCPD-14457
BiGG IDNot Available
Wikipedia LinkErgometrine
METLIN IDNot Available
PubChem Compound443884
PDB IDNot Available
ChEBI ID4822
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Moubarak AS, Rosenkrans CF Jr, Johnson ZB: Modulation of cytochrome P450 metabolism by ergonovine and dihydroergotamine. Vet Hum Toxicol. 2003 Feb;45(1):6-9. [PubMed:12583687 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
References
  1. Gibson A, Carvajal A: Agonist profile of ergometrine (ergonovine) on a population of postsynaptic alpha-adrenoceptors. J Pharm Pharmacol. 1988 Feb;40(2):137-9. [PubMed:2897449 ]
  2. Zhu F, Han B, Kumar P, Liu X, Ma X, Wei X, Huang L, Guo Y, Han L, Zheng C, Chen Y: Update of TTD: Therapeutic Target Database. Nucleic Acids Res. 2010 Jan;38(Database issue):D787-91. doi: 10.1093/nar/gkp1014. Epub 2009 Nov 20. [PubMed:19933260 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. [PubMed:11961113 ]
  2. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. [PubMed:12235267 ]