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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
Data?1582752363
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
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point130 - 131 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0061 g/LALOGPS
logP10(1.93) g/LALOGPS
logP10(1.8) g/LChemAxon
logS10(-5) g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+228.00831661259
DarkChem[M-H]-218.68631661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Endomorphin-2,1TMS,#1C[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H](CC2=CC=CC=C2)C(N)=O)C=C14935.9Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Endomorphin-2,1TMS,#2C[Si](C)(C)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)=O4972.6Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Endomorphin-2,1TMS,#3C[Si](C)(C)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CC1=CC=C(O)C=C14947.2Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Endomorphin-2,1TMS,#4C[Si](C)(C)N(C(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CC1=CC=C(O)C=C1)[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(N)=O4869.4Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Endomorphin-2,1TMS,#5C[Si](C)(C)N(C(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CC1=CC=C(O)C=C1)[C@@H](CC1=CC=CC=C1)C(N)=O4840.9Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Endomorphin-2,1TBDMS,#1CC(C)(C)[Si](C)(C)OC1=CC=C(C[C@H](N)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H](CC2=CC=CC=C2)C(N)=O)C=C15226.8Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Endomorphin-2,1TBDMS,#2CC(C)(C)[Si](C)(C)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)=O5173.1Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Endomorphin-2,1TBDMS,#3CC(C)(C)[Si](C)(C)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CC1=CC=C(O)C=C15135.4Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Endomorphin-2,1TBDMS,#4CC(C)(C)[Si](C)(C)N(C(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CC1=CC=C(O)C=C1)[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)C(N)=O5083.6Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Endomorphin-2,1TBDMS,#5CC(C)(C)[Si](C)(C)N(C(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CC1=CC=C(O)C=C1)[C@@H](CC1=CC=CC=C1)C(N)=O5059.3Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Endomorphin-2 GC-MS (Non-derivatized) - 70eV, Positivesplash10-01qi-7632920000-61c9c3747ad919a34c4d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Endomorphin-2 GC-MS (1 TMS) - 70eV, Positivesplash10-0zfu-9443853000-b0f6cf2c32cb5ac7bcca2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Endomorphin-2 GC-MS ("Endomorphin-2,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endomorphin-2 10V, Positive-QTOFsplash10-0ab9-0532290000-d0fd32e7d5d368aa05e92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endomorphin-2 20V, Positive-QTOFsplash10-00yr-1942010000-5ab5f523355007c7035d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endomorphin-2 40V, Positive-QTOFsplash10-00xr-5930000000-cd6666801968bdeee2462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endomorphin-2 10V, Negative-QTOFsplash10-00di-0101190000-e9403040412cd1a9fc722017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endomorphin-2 20V, Negative-QTOFsplash10-03di-2965550000-1bb3d8a636a7d6c560622017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endomorphin-2 40V, Negative-QTOFsplash10-01ox-9741100000-f250d43c7be9e88c4b872017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endomorphin-2 10V, Positive-QTOFsplash10-05fr-0200190000-588c4199c498359ce9ae2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endomorphin-2 20V, Positive-QTOFsplash10-0abj-0900230000-da52f0e85cfb83709a362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endomorphin-2 40V, Positive-QTOFsplash10-00dj-5900000000-8a102e76f50fa2d169952021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endomorphin-2 10V, Negative-QTOFsplash10-00di-0000190000-3c226367db9570ed339a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endomorphin-2 20V, Negative-QTOFsplash10-05fu-5335790000-c4bd1a1b31a969d34acc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Endomorphin-2 40V, Negative-QTOFsplash10-00kf-9683200000-5dde9bfa06e8110d9fc82021-09-22Wishart LabView Spectrum
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)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 ]