Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:34 UTC
Update Date2021-09-14 15:29:57 UTC
HMDB IDHMDB0002053
Secondary Accession Numbers
  • HMDB02053
Metabolite Identification
Common NameHistidylproline diketopiperazine
DescriptionHistidylproline diketopiperazine is a cyclic dipeptide initially described in both the hypothalamus and cerebral tissues, has been detected in various sites outside the central nervous system, including the gastrointestinal tract and, more specifically, the endocrine pancreas. Histidylproline diketopiperazine belongs to the family of Dioxopiperazines. These are compounds containing a piperazine ring bearing two ketone groups.
Structure
Data?1582752225
Synonyms
ValueSource
His-pro-DKPMeSH
Cyclo(his-pro)MeSH
Cyclo(histidyl-prolyl)MeSH
Histidyl-proline diketopiperazineMeSH
Histidyl-proline diketopiperazine, (3R-cis)-isomerMeSH
Histidyl-proline diketopiperazine, (3S-cis)-isomerMeSH
Histidyl-proline diketopiperazine, (3S-trans)-isomerMeSH
Histidyl-proline-diketopiperazineMeSH
Chemical FormulaC12H16N4O2
Average Molecular Weight248.281
Monoisotopic Molecular Weight248.127325776
IUPAC Name(3S,9aS)-3-(1H-imidazol-5-ylmethyl)-octahydro-1H-pyrido[1,2-a]piperazine-1,4-dione
Traditional Name(3S,9aS)-3-(3H-imidazol-4-ylmethyl)-hexahydro-2H-pyrido[1,2-a]piperazine-1,4-dione
CAS Registry Number53109-32-3
SMILES
[H][C@@]12CCCCN1C(=O)[C@H](CC1=CN=CN1)NC2=O
InChI Identifier
InChI=1S/C12H16N4O2/c17-11-10-3-1-2-4-16(10)12(18)9(15-11)5-8-6-13-7-14-8/h6-7,9-10H,1-5H2,(H,13,14)(H,15,17)/t9-,10-/m0/s1
InChI KeyLCXWQHWWTPOAFI-UWVGGRQHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Piperidine
  • Azole
  • Imidazole
  • Tertiary carboxylic acid amide
  • Cyclic carboximidic acid
  • Heteroaromatic compound
  • Lactam
  • Carboxamide group
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility9.12 g/LALOGPS
logP-0.36ALOGPS
logP-1.1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)10.95ChemAxon
pKa (Strongest Basic)6.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area78.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.45 m³·mol⁻¹ChemAxon
Polarizability24.5 ųChemAxon
Number of Rings3ChemAxon
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]+157.87231661259
DarkChem[M-H]-156.70731661259
DeepCCS[M-2H]-183.32630932474
DeepCCS[M+Na]+158.28530932474
AllCCS[M+H]+157.632859911
AllCCS[M+H-H2O]+153.832859911
AllCCS[M+NH4]+161.032859911
AllCCS[M+Na]+162.032859911
AllCCS[M-H]-160.232859911
AllCCS[M+Na-2H]-159.832859911
AllCCS[M+HCOO]-159.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Histidylproline diketopiperazine[H][C@@]12CCCCN1C(=O)[C@H](CC1=CN=CN1)NC2=O3465.1Standard polar33892256
Histidylproline diketopiperazine[H][C@@]12CCCCN1C(=O)[C@H](CC1=CN=CN1)NC2=O2620.7Standard non polar33892256
Histidylproline diketopiperazine[H][C@@]12CCCCN1C(=O)[C@H](CC1=CN=CN1)NC2=O2721.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Histidylproline diketopiperazine,1TMS,isomer #1C[Si](C)(C)N1C=NC=C1C[C@@H]1NC(=O)[C@@H]2CCCCN2C1=O2544.1Semi standard non polar33892256
Histidylproline diketopiperazine,1TMS,isomer #1C[Si](C)(C)N1C=NC=C1C[C@@H]1NC(=O)[C@@H]2CCCCN2C1=O2478.0Standard non polar33892256
Histidylproline diketopiperazine,1TMS,isomer #1C[Si](C)(C)N1C=NC=C1C[C@@H]1NC(=O)[C@@H]2CCCCN2C1=O4206.8Standard polar33892256
Histidylproline diketopiperazine,1TMS,isomer #2C[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=C[NH]12307.8Semi standard non polar33892256
Histidylproline diketopiperazine,1TMS,isomer #2C[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=C[NH]12410.2Standard non polar33892256
Histidylproline diketopiperazine,1TMS,isomer #2C[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=C[NH]13721.4Standard polar33892256
Histidylproline diketopiperazine,2TMS,isomer #1C[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=CN1[Si](C)(C)C2384.4Semi standard non polar33892256
Histidylproline diketopiperazine,2TMS,isomer #1C[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=CN1[Si](C)(C)C2461.3Standard non polar33892256
Histidylproline diketopiperazine,2TMS,isomer #1C[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=CN1[Si](C)(C)C3511.8Standard polar33892256
Histidylproline diketopiperazine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=NC=C1C[C@@H]1NC(=O)[C@@H]2CCCCN2C1=O2791.7Semi standard non polar33892256
Histidylproline diketopiperazine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=NC=C1C[C@@H]1NC(=O)[C@@H]2CCCCN2C1=O2717.7Standard non polar33892256
Histidylproline diketopiperazine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=NC=C1C[C@@H]1NC(=O)[C@@H]2CCCCN2C1=O4269.3Standard polar33892256
Histidylproline diketopiperazine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=C[NH]12518.1Semi standard non polar33892256
Histidylproline diketopiperazine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=C[NH]12652.7Standard non polar33892256
Histidylproline diketopiperazine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=C[NH]13752.8Standard polar33892256
Histidylproline diketopiperazine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=CN1[Si](C)(C)C(C)(C)C2804.2Semi standard non polar33892256
Histidylproline diketopiperazine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=CN1[Si](C)(C)C(C)(C)C2919.4Standard non polar33892256
Histidylproline diketopiperazine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)[C@@H]2CCCCN2C(=O)[C@@H]1CC1=CN=CN1[Si](C)(C)C(C)(C)C3481.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Histidylproline diketopiperazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0c10-8960000000-b59521a7bf7f2dbcd98b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Histidylproline diketopiperazine 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 - Histidylproline diketopiperazine 10V, Positive-QTOFsplash10-0002-0090000000-843d3723786addf5c81b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 20V, Positive-QTOFsplash10-006t-0090000000-38a066bbd349061998cc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 40V, Positive-QTOFsplash10-001i-9100000000-98e8fd70b7c52af6ad802017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 10V, Negative-QTOFsplash10-0002-0190000000-1981c342d35a74baaaf52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 20V, Negative-QTOFsplash10-001j-8940000000-df121bc941f701b83e432017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 40V, Negative-QTOFsplash10-001i-9400000000-bb22aeb05ef45a82e9032017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 10V, Positive-QTOFsplash10-0002-0090000000-2d6df444943bd8abf9e02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 20V, Positive-QTOFsplash10-0002-0090000000-7a61131b9929146e0cc32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 40V, Positive-QTOFsplash10-000t-9560000000-d98006bfa210732b955f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 10V, Negative-QTOFsplash10-0002-0090000000-9825da4495af4eed0ee22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 20V, Negative-QTOFsplash10-0002-1290000000-03e21d76de28525b9ad92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Histidylproline diketopiperazine 40V, Negative-QTOFsplash10-0006-9410000000-f6ed33b9456dfc589d832021-09-24Wishart 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
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000022 (0.000011-0.000033) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022818
KNApSAcK IDNot Available
Chemspider ID58646
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound65137
PDB IDNot Available
ChEBI ID90039
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMa, Yaping; Bai, Wei; Zhong, Fei; Cui, Xueyun. Method for the preparation of all stereoisomers of cyclo(histidylproline). Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 11pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Leduque P, Jackson IM, Kervran A, Aratan-Spire S, Czernichow P, Dubois PM: Histidyl-proline diketopiperazine (His-Pro DKP) immunoreactivity is present in the glucagon-containing cells of the human fetal pancreas. J Clin Invest. 1987 Mar;79(3):875-80. [PubMed:3102558 ]
  2. Takahara Y, Battaini F, Ross DD, Akman SA, Bachur NR, Bailey KR, Lakatos E, Peterkofsky A: Detection in human serum by radioimmunoassay of histidyl-proline diketopiperazine, a metabolite of thyrotropin-releasing hormone. J Clin Endocrinol Metab. 1983 Feb;56(2):312-9. [PubMed:6401750 ]