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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-03-04 20:24:46 UTC
Update Date2021-09-14 15:36:54 UTC
HMDB IDHMDB0059792
Secondary Accession Numbers
  • HMDB59792
Metabolite Identification
Common NameOpiorphin
DescriptionOpiorphin is an endogenous 5-residue opioid peptide (Gln-Arg-Phe-Ser-Arg) first isolated from human saliva. Initial research with mice shows the compound has a painkilling effect greater than that of morphine. It works by stopping the normal breakdown of enkephalins, natural pain-killing opioids in the spinal cord. Opiorphin originates from the N-terminal region of the protein PROL1 (proline rich, lacrimal 1) and inhibits three proteases: neutral ecto-endopeptidase (MME), ecto-aminopeptidase N (ANPEP) and a dipeptidyl peptidase DPP3. This protease inhibitory action extends the duration of enkephalins, which are natural pain killers that are released in response to specific potentially painful stimuli.
Structure
Data?1563865975
Synonyms
ValueSource
GLN-Arg-phe-ser-argHMDB
QRFSR PeptideHMDB
Glutaminyl-arginyl-phenylalanyl-seryl-arginineHMDB
Chemical FormulaC29H48N12O8
Average Molecular Weight692.767
Monoisotopic Molecular Weight692.371806572
IUPAC Name(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-1,3-dihydroxypropylidene]amino}-5-carbamimidamidopentanoic acid
Traditional Name(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}-1,3-dihydroxypropylidene]amino}-5-carbamimidamidopentanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(CCC(O)=N)C(O)=N[C@@]([H])(CCCNC(N)=N)C(O)=N[C@@]([H])(CC1=CC=CC=C1)C(O)=N[C@@]([H])(CO)C(O)=N[C@@]([H])(CCCNC(N)=N)C(O)=O
InChI Identifier
InChI=1S/C29H48N12O8/c30-17(10-11-22(31)43)23(44)38-18(8-4-12-36-28(32)33)24(45)40-20(14-16-6-2-1-3-7-16)25(46)41-21(15-42)26(47)39-19(27(48)49)9-5-13-37-29(34)35/h1-3,6-7,17-21,42H,4-5,8-15,30H2,(H2,31,43)(H,38,44)(H,39,47)(H,40,45)(H,41,46)(H,48,49)(H4,32,33,36)(H4,34,35,37)/t17-,18-,19-,20-,21-/m0/s1
InChI KeyTWWFCOBVAKAKIT-SXYSDOLCSA-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
  • Glutamine or derivatives
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Serine or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Benzenoid
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Guanidine
  • Primary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Alcohol
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Primary amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP-2ALOGPS
logP-6.9ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.31ChemAxon
pKa (Strongest Basic)12.3ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area381.79 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity208.34 m³·mol⁻¹ChemAxon
Polarizability71.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+230.93530932474
DeepCCS[M-H]-228.5430932474
DeepCCS[M-2H]-262.36530932474
DeepCCS[M+Na]+237.09130932474
AllCCS[M+H]+253.632859911
AllCCS[M+H-H2O]+253.332859911
AllCCS[M+NH4]+253.832859911
AllCCS[M+Na]+253.832859911
AllCCS[M-H]-249.332859911
AllCCS[M+Na-2H]-253.132859911
AllCCS[M+HCOO]-257.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Opiorphin[H][C@](N)(CCC(O)=N)C(O)=N[C@@]([H])(CCCNC(N)=N)C(O)=N[C@@]([H])(CC1=CC=CC=C1)C(O)=N[C@@]([H])(CO)C(O)=N[C@@]([H])(CCCNC(N)=N)C(O)=O4876.5Standard polar33892256
Opiorphin[H][C@](N)(CCC(O)=N)C(O)=N[C@@]([H])(CCCNC(N)=N)C(O)=N[C@@]([H])(CC1=CC=CC=C1)C(O)=N[C@@]([H])(CO)C(O)=N[C@@]([H])(CCCNC(N)=N)C(O)=O5275.7Standard non polar33892256
Opiorphin[H][C@](N)(CCC(O)=N)C(O)=N[C@@]([H])(CCCNC(N)=N)C(O)=N[C@@]([H])(CC1=CC=CC=C1)C(O)=N[C@@]([H])(CO)C(O)=N[C@@]([H])(CCCNC(N)=N)C(O)=O6922.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9240535000-837e548c02bd3266bd2b2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_1_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_1_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_1_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_1_15) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Opiorphin GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Opiorphin 10V, Positive-QTOFsplash10-0729-1520219000-ae63d44cc1d9e984abb42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Opiorphin 20V, Positive-QTOFsplash10-0nt9-4950212000-2fae7176985aec3dbfad2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Opiorphin 40V, Positive-QTOFsplash10-114i-6920000000-3de2c9545a91010bb1a82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Opiorphin 10V, Negative-QTOFsplash10-05u7-0000009000-8803c4f7c24df02272f62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Opiorphin 20V, Negative-QTOFsplash10-0a59-3100009000-1970d4b1ed57fb79997b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Opiorphin 40V, Negative-QTOFsplash10-052f-9310101000-661b0929abbcf656ed4c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Opiorphin 10V, Negative-QTOFsplash10-0006-0000009000-c01f25ad5b9e25ebf0812021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Opiorphin 20V, Negative-QTOFsplash10-00dl-2200069000-576b7aaa12ddce82feaa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Opiorphin 40V, Negative-QTOFsplash10-009f-8289300000-a03b7ee7facef173ee322021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Opiorphin 10V, Positive-QTOFsplash10-0006-0000009000-b52aa8be01313f3baf9a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Opiorphin 20V, Positive-QTOFsplash10-004i-1200009000-aacfc34201b4b1e2c0cb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Opiorphin 40V, Positive-QTOFsplash10-0zfr-9800010000-36db38438cc4310e66612021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart 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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOpiorphin
METLIN IDNot Available
PubChem Compound25195667
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available