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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-12-19 20:58:00 UTC
Update Date2021-09-14 15:37:14 UTC
HMDB IDHMDB0005774
Secondary Accession Numbers
  • HMDB05774
Metabolite Identification
Common NameEndomorphin-2
DescriptionEndomorphin-2 belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Endomorphin-2 has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make endomorphin-2 a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Endomorphin-2.
Structure
Thumb
Synonyms
ValueSource
Endomorphin 2HMDB
H-Tyr-pro-phe-phe-NH2HMDB
Tyrosyl-prolyl-phenylalanyl-phenylalaninamideMeSH, HMDB
Tyr-pro-phe-phe-NH2MeSH, 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-phenylpropanimidateGenerator, HMDB
Endomorphin-2MeSH
L-Tyrosyl-L-prolyl-L-phenylalanyl-L-phenylalaninamideMeSH, HMDB
Tetrapeptide-15MeSH, HMDB
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
Description Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflav-2-enes
Direct ParentIsoflavones
Alternative Parents
Substituents
  • Hydroxyisoflavonoid
  • Isoflavone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point130 - 131 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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)Not Available
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 ]