Endomorphin-1 (CHEM035990)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:07:02 UTC
Update Date2016-11-09 01:21:24 UTC
Accession NumberCHEM035990
Identification
Common NameEndomorphin-1
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Endomorphin 1ChEMBL, HMDB
H-Tyr-pro-TRP-phe-NH2HMDB
(DMT1)Endomorphin-1MeSH, HMDB
Tyr-pro-TRP-phe-NH2MeSH, HMDB
Tyrosyl-prolyl-tryptophyl-phenylalaninamideMeSH, HMDB
(2S)-2-({[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-N-[(1S)-1-(C-hydroxycarbonimidoyl)-2-phenylethyl]-3-(1H-indol-3-yl)propanimidateGenerator, HMDB
Endomorphin-1MeSH
Chemical FormulaC34H38N6O5
Average Molecular Mass610.703 g/mol
Monoisotopic Mass610.290 g/mol
CAS Registry Number189388-22-5
IUPAC Name(2S)-2-{[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-N-[(1S)-1-carbamoyl-2-phenylethyl]-3-(1H-indol-3-yl)propanamide
Traditional Name(2S)-2-{[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-N-[(1S)-1-carbamoyl-2-phenylethyl]-3-(1H-indol-3-yl)propanamide
SMILESN[C@@H](CC1=CC=C(O)C=C1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(=O)N[C@@H](CC1=CC=CC=C1)C(N)=O
InChI IdentifierInChI=1S/C34H38N6O5/c35-26(17-22-12-14-24(41)15-13-22)34(45)40-16-6-11-30(40)33(44)39-29(19-23-20-37-27-10-5-4-9-25(23)27)32(43)38-28(31(36)42)18-21-7-2-1-3-8-21/h1-5,7-10,12-15,20,26,28-30,37,41H,6,11,16-19,35H2,(H2,36,42)(H,38,43)(H,39,44)/t26-,28-,29-,30-/m0/s1
InChI KeyZEXLJFNSKAHNFH-SYKYGTKKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Phenylalanine or derivatives
  • Proline or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Triptan
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Aralkylamine
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Fatty amide
  • Substituted pyrrole
  • Pyrrole
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Primary carboxylic acid amide
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Primary amine
  • Organic oxide
  • Amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0054 g/LALOGPS
logP2.15ALOGPS
logP1.9ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)7.72ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area183.64 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity168.83 m³·mol⁻¹ChemAxon
Polarizability65.34 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01bl-9840760000-e1462042be3a35cc48c4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0019-3950030000-3cfb504236224b14eb64Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Endomorphin-1,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0962787000-08fed61e4a8e9103704fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06dr-1931210000-8a328ec998de29d776c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abi-5930000000-a012d3c9cffafe0aa1e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0110449000-259fef8bc67f5c3130b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ea-2764931000-9e7efa126e41c1719ad1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9741100000-7f04b5c5fb2273b7131aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000109000-e20a2c480ec099b0435eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4m-4423926000-36f7964f4b61c2bf2645Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kwf-6931200000-3fdae321b61b0dbe17d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0300139000-4d51524d3e5a23acb99dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06rm-0900321000-72f1692dd6486272e1e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xu-4900000000-1192a5fe01b240f4f1c9Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0005773
FooDB IDFDB023763
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEndomorphin-1
Chemspider ID4470614
ChEBI ID239449
PubChem Compound ID5311080
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Cardillo, Giuliana; Gentilucci, Luca; Qasem, Ahmed R.; Sgarzi, Fabio; Spampinato, Santi. Endomorphin-1 Analogues Containing b-Proline Are m-Opioid Receptor Agonists and Display Enhanced Enzymatic Hydrolysis Resistance. Journal of Medicinal Chemistry (2002
2. Irnaten M, Aicher SA, Wang J, Venkatesan P, Evans C, Baxi S, Mendelowitz D: Mu-opioid receptors are located postsynaptically and endomorphin-1 inhibits voltage-gated calcium currents in premotor cardiac parasympathetic neurons in the rat nucleus ambiguus. Neuroscience. 2003;116(2):573-82.
3. Yu Y, Cui Y, Wang X, Fan YZ, Liu J, Yan X, Wang R: Endomorphin1 and endomorphin2, endogenous potent inhibitors of electrical field stimulation (EFS)-induced cholinergic contractions of rat isolated bronchus. Peptides. 2006 Jul;27(7):1846-51. Epub 2006 Mar 27.
4. Whitten RD, Martin-Schild S, Zadina JE, Albers HE: Endomorphin1-like immunoreactivity in the limbic system of Syrian hamsters (Mesocricetus auratus). Brain Res Bull. 2001 Dec;56(6):563-7.
5. Feng Y, Zhao QY, Chen Q, Wang R: Vasorelaxant responses to endomorphin1[psi] and endomorphin2[psi], analogues of endomorphins, in rat aorta rings. Pharmazie. 2005 Nov;60(11):851-5.
6. Yu Y, Wang CL, Cui Y, Fan YZ, Liu J, Shao X, Liu HM, Wang R: C-terminal amide to alcohol conversion changes the cardiovascular effects of endomorphins in anesthetized rats. Peptides. 2006 Jan;27(1):136-43. Epub 2005 Sep 1.
7. Koda Y, Liang MT, Blanchfield JT, Toth I: In vitro stability and permeability studies of liposomal delivery systems for a novel lipophilic endomorphin 1 analogue. Int J Pharm. 2008 May 22;356(1-2):37-43. doi: 10.1016/j.ijpharm.2007.12.036. Epub 2008 Jan 4.