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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:03:24 UTC
Update Date2022-09-22 18:34:23 UTC
HMDB IDHMDB0029026
Secondary Accession Numbers
  • HMDB29026
Metabolite Identification
Common NameProlyl-Serine
DescriptionProlyl-Serine is a dipeptide composed of proline and serine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite.
Structure
Data?1582753367
Synonyms
ValueSource
L-Prolyl-L-serineHMDB
p-S DipeptideHMDB
Pro-serHMDB
Proline serine dipeptideHMDB
Proline-serine dipeptideHMDB
ProlylserineHMDB
PS DipeptideHMDB
3-Hydroxy-2-{[hydroxy(pyrrolidin-2-yl)methylidene]amino}propanoateHMDB
Prolyl-serineMeSH
Chemical FormulaC8H14N2O4
Average Molecular Weight202.2078
Monoisotopic Molecular Weight202.095356946
IUPAC Name3-hydroxy-2-[(pyrrolidin-2-yl)formamido]propanoic acid
Traditional Name3-hydroxy-2-(pyrrolidin-2-ylformamido)propanoic acid
CAS Registry NumberNot Available
SMILES
OCC(NC(=O)C1CCCN1)C(O)=O
InChI Identifier
InChI=1S/C8H14N2O4/c11-4-6(8(13)14)10-7(12)5-2-1-3-9-5/h5-6,9,11H,1-4H2,(H,10,12)(H,13,14)
InChI KeyAFWBWPCXSWUCLB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Proline or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Serine or derivatives
  • Alpha-amino acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • Beta-hydroxy acid
  • Hydroxy acid
  • Pyrrolidine
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Secondary aliphatic amine
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-4.16Extrapolated
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility14.6 g/LALOGPS
logP-3.2ALOGPS
logP-4.2ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.5ChemAxon
pKa (Strongest Basic)9.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area98.66 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity46.91 m³·mol⁻¹ChemAxon
Polarizability19.72 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+144.0931661259
DarkChem[M-H]-144.29731661259
DeepCCS[M+H]+138.94730932474
DeepCCS[M-H]-135.11930932474
DeepCCS[M-2H]-172.54330932474
DeepCCS[M+Na]+148.08230932474
AllCCS[M+H]+143.832859911
AllCCS[M+H-H2O]+139.932859911
AllCCS[M+NH4]+147.432859911
AllCCS[M+Na]+148.432859911
AllCCS[M-H]-141.632859911
AllCCS[M+Na-2H]-142.232859911
AllCCS[M+HCOO]-142.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Prolyl-SerineOCC(NC(=O)C1CCCN1)C(O)=O2983.3Standard polar33892256
Prolyl-SerineOCC(NC(=O)C1CCCN1)C(O)=O1795.9Standard non polar33892256
Prolyl-SerineOCC(NC(=O)C1CCCN1)C(O)=O2008.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prolyl-Serine,1TMS,isomer #1C[Si](C)(C)OCC(NC(=O)C1CCCN1)C(=O)O1944.7Semi standard non polar33892256
Prolyl-Serine,1TMS,isomer #2C[Si](C)(C)OC(=O)C(CO)NC(=O)C1CCCN11945.1Semi standard non polar33892256
Prolyl-Serine,1TMS,isomer #3C[Si](C)(C)N(C(=O)C1CCCN1)C(CO)C(=O)O1950.1Semi standard non polar33892256
Prolyl-Serine,1TMS,isomer #4C[Si](C)(C)N1CCCC1C(=O)NC(CO)C(=O)O1954.3Semi standard non polar33892256
Prolyl-Serine,2TMS,isomer #1C[Si](C)(C)OCC(NC(=O)C1CCCN1)C(=O)O[Si](C)(C)C1972.6Semi standard non polar33892256
Prolyl-Serine,2TMS,isomer #2C[Si](C)(C)OCC(C(=O)O)N(C(=O)C1CCCN1)[Si](C)(C)C1960.0Semi standard non polar33892256
Prolyl-Serine,2TMS,isomer #3C[Si](C)(C)OCC(NC(=O)C1CCCN1[Si](C)(C)C)C(=O)O1981.9Semi standard non polar33892256
Prolyl-Serine,2TMS,isomer #4C[Si](C)(C)OC(=O)C(CO)N(C(=O)C1CCCN1)[Si](C)(C)C1924.0Semi standard non polar33892256
Prolyl-Serine,2TMS,isomer #5C[Si](C)(C)OC(=O)C(CO)NC(=O)C1CCCN1[Si](C)(C)C1965.8Semi standard non polar33892256
Prolyl-Serine,2TMS,isomer #6C[Si](C)(C)N1CCCC1C(=O)N(C(CO)C(=O)O)[Si](C)(C)C1925.5Semi standard non polar33892256
Prolyl-Serine,3TMS,isomer #1C[Si](C)(C)OCC(C(=O)O[Si](C)(C)C)N(C(=O)C1CCCN1)[Si](C)(C)C1945.5Semi standard non polar33892256
Prolyl-Serine,3TMS,isomer #1C[Si](C)(C)OCC(C(=O)O[Si](C)(C)C)N(C(=O)C1CCCN1)[Si](C)(C)C2033.4Standard non polar33892256
Prolyl-Serine,3TMS,isomer #2C[Si](C)(C)OCC(NC(=O)C1CCCN1[Si](C)(C)C)C(=O)O[Si](C)(C)C1992.7Semi standard non polar33892256
Prolyl-Serine,3TMS,isomer #2C[Si](C)(C)OCC(NC(=O)C1CCCN1[Si](C)(C)C)C(=O)O[Si](C)(C)C2045.5Standard non polar33892256
Prolyl-Serine,3TMS,isomer #3C[Si](C)(C)OCC(C(=O)O)N(C(=O)C1CCCN1[Si](C)(C)C)[Si](C)(C)C2017.6Semi standard non polar33892256
Prolyl-Serine,3TMS,isomer #3C[Si](C)(C)OCC(C(=O)O)N(C(=O)C1CCCN1[Si](C)(C)C)[Si](C)(C)C2066.0Standard non polar33892256
Prolyl-Serine,3TMS,isomer #4C[Si](C)(C)OC(=O)C(CO)N(C(=O)C1CCCN1[Si](C)(C)C)[Si](C)(C)C1970.7Semi standard non polar33892256
Prolyl-Serine,3TMS,isomer #4C[Si](C)(C)OC(=O)C(CO)N(C(=O)C1CCCN1[Si](C)(C)C)[Si](C)(C)C2027.2Standard non polar33892256
Prolyl-Serine,4TMS,isomer #1C[Si](C)(C)OCC(C(=O)O[Si](C)(C)C)N(C(=O)C1CCCN1[Si](C)(C)C)[Si](C)(C)C2043.3Semi standard non polar33892256
Prolyl-Serine,4TMS,isomer #1C[Si](C)(C)OCC(C(=O)O[Si](C)(C)C)N(C(=O)C1CCCN1[Si](C)(C)C)[Si](C)(C)C2116.2Standard non polar33892256
Prolyl-Serine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(NC(=O)C1CCCN1)C(=O)O2200.7Semi standard non polar33892256
Prolyl-Serine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(CO)NC(=O)C1CCCN12220.4Semi standard non polar33892256
Prolyl-Serine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C(=O)C1CCCN1)C(CO)C(=O)O2213.4Semi standard non polar33892256
Prolyl-Serine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1CCCC1C(=O)NC(CO)C(=O)O2232.7Semi standard non polar33892256
Prolyl-Serine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(NC(=O)C1CCCN1)C(=O)O[Si](C)(C)C(C)(C)C2456.1Semi standard non polar33892256
Prolyl-Serine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(C(=O)O)N(C(=O)C1CCCN1)[Si](C)(C)C(C)(C)C2439.0Semi standard non polar33892256
Prolyl-Serine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OCC(NC(=O)C1CCCN1[Si](C)(C)C(C)(C)C)C(=O)O2493.1Semi standard non polar33892256
Prolyl-Serine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(CO)N(C(=O)C1CCCN1)[Si](C)(C)C(C)(C)C2408.5Semi standard non polar33892256
Prolyl-Serine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)C(CO)NC(=O)C1CCCN1[Si](C)(C)C(C)(C)C2488.0Semi standard non polar33892256
Prolyl-Serine,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N1CCCC1C(=O)N(C(CO)C(=O)O)[Si](C)(C)C(C)(C)C2445.0Semi standard non polar33892256
Prolyl-Serine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)C1CCCN1)[Si](C)(C)C(C)(C)C2633.3Semi standard non polar33892256
Prolyl-Serine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)C1CCCN1)[Si](C)(C)C(C)(C)C2640.6Standard non polar33892256
Prolyl-Serine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(NC(=O)C1CCCN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2714.6Semi standard non polar33892256
Prolyl-Serine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(NC(=O)C1CCCN1[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2645.9Standard non polar33892256
Prolyl-Serine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OCC(C(=O)O)N(C(=O)C1CCCN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2708.1Semi standard non polar33892256
Prolyl-Serine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OCC(C(=O)O)N(C(=O)C1CCCN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2644.2Standard non polar33892256
Prolyl-Serine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(CO)N(C(=O)C1CCCN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2673.5Semi standard non polar33892256
Prolyl-Serine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C(CO)N(C(=O)C1CCCN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2622.4Standard non polar33892256
Prolyl-Serine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)C1CCCN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2909.2Semi standard non polar33892256
Prolyl-Serine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)C1CCCN1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2866.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prolyl-Serine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-9200000000-a2e1c43a60d998ade8702017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prolyl-Serine GC-MS (2 TMS) - 70eV, Positivesplash10-006x-4911000000-62f941df9c46d42b32a62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prolyl-Serine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolyl-Serine 10V, Negative-QTOFsplash10-0udi-0970000000-2a87d4ea4e3edd70878c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolyl-Serine 20V, Negative-QTOFsplash10-0kh0-2910000000-f01c94896906425edddc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolyl-Serine 40V, Negative-QTOFsplash10-0m4x-9100000000-b0551484143a8f22961f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolyl-Serine 10V, Negative-QTOFsplash10-0udi-3970000000-eec432cf112f7acdcd452021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolyl-Serine 20V, Negative-QTOFsplash10-0002-9000000000-a033727829f70a61d04a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolyl-Serine 40V, Negative-QTOFsplash10-00y0-9000000000-806ab4917bf004779efc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolyl-Serine 10V, Positive-QTOFsplash10-0f79-8960000000-00d20447c8194c18c59e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolyl-Serine 20V, Positive-QTOFsplash10-00di-9100000000-c4faed593d29fa3f88db2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolyl-Serine 40V, Positive-QTOFsplash10-00di-9000000000-6c9be2c12ee63027f2412017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolyl-Serine 10V, Positive-QTOFsplash10-006t-9000000000-78859c2e610cdd14b9a32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolyl-Serine 20V, Positive-QTOFsplash10-00di-9000000000-7a5c6955a88a797e0cd72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prolyl-Serine 40V, Positive-QTOFsplash10-00di-9000000000-d45e95ab488065eef6382021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Metastatic melanoma
details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Metastatic melanoma
  1. Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112034
KNApSAcK IDNot Available
Chemspider ID16568367
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound18218236
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 References
  1. Akarca US, Greene S, Lok AS: Detection of precore hepatitis B virus mutants in asymptomatic HBsAg-positive family members. Hepatology. 1994 Jun;19(6):1366-70. [PubMed:8188166 ]