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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-12-19 20:58:00 UTC
Update Date2017-12-07 01:55:29 UTC
HMDB IDHMDB0005774
Secondary Accession Numbers
  • HMDB05774
Metabolite Identification
Common NameEndomorphin-2
DescriptionEndomorphin-1 (H-Tyr-Pro-Trp-Phe-NH2) and endomorphin-2 (H-Tyr-Pro-Phe-Phe-NH2) are peptide amides with the highest known affinity and specificity for the mu-opioid receptor.
Structure
Thumb
Synonyms
ValueSource
Endomorphin 2HMDB
H-Tyr-pro-phe-phe-NH2HMDB
Tyrosyl-prolyl-phenylalanyl-phenylalaninamideMeSH
Tyr-pro-phe-phe-NH2MeSH
Chemical FormulaC32H37N5O5
Average Molecular Weight571.6667
Monoisotopic Molecular Weight571.279469319
IUPAC Name(2S)-2-{[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-N-[(1S)-1-carbamoyl-2-phenylethyl]-3-phenylpropanamide
Traditional Name(2S)-2-{[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-N-[(1S)-1-carbamoyl-2-phenylethyl]-3-phenylpropanamide
CAS Registry Number141801-26-5
SMILES
N[C@@H](CC1=CC=C(O)C=C1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(N)=O
InChI Identifier
InChI=1S/C32H37N5O5/c33-25(18-23-13-15-24(38)16-14-23)32(42)37-17-7-12-28(37)31(41)36-27(20-22-10-5-2-6-11-22)30(40)35-26(29(34)39)19-21-8-3-1-4-9-21/h1-6,8-11,13-16,25-28,38H,7,12,17-20,33H2,(H2,34,39)(H,35,40)(H,36,41)/t25-,26-,27-,28-/m0/s1
InChI KeyXIJHWXXXIMEHKW-LJWNLINESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Phenylalanine or derivatives
  • Proline or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • N-acylpyrrolidine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Fatty amide
  • Benzenoid
  • Fatty acyl
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Primary amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point130 - 131 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0061 g/LALOGPS
logP1.93ALOGPS
logP1.8ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)7.72ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area167.85 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity157.74 m³·mol⁻¹ChemAxon
Polarizability61.25 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01qi-7632920000-61c9c3747ad919a34c4dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0zfu-9443853000-b0f6cf2c32cb5ac7bccaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0532290000-d0fd32e7d5d368aa05e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00yr-1942010000-5ab5f523355007c7035dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-5930000000-cd6666801968bdeee246View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0101190000-e9403040412cd1a9fc72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2965550000-1bb3d8a636a7d6c56062View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9741100000-f250d43c7be9e88c4b87View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023764
KNApSAcK IDNot Available
Chemspider ID4470615
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEndomorphin-2
METLIN IDNot Available
PubChem Compound5311081
PDB IDNot Available
ChEBI ID297398
References
Synthesis ReferenceShimizu, Yoshiro; Takahashi, Motohiro; Fukumizu, Atsuko; Tsuda, Yuko; Bryant, Sharon D.; Lazarus, Lawrence H.; Okada, Yoshio. Synthesis of endomorphin analogs and studies on the structure-opioid receptor-binding activity relationship. Peptide Science (1999), Volume Date 1998, 35th 197-200.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:16564113 ]
  2. 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. [PubMed:16320949 ]
  3. 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. [PubMed:16139930 ]