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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2019-04-04 16:09:28 UTC
Update Date2022-09-22 17:44:16 UTC
HMDB IDHMDB0240345
Secondary Accession NumbersNone
Metabolite Identification
Common NameN2,N5-Diacetylornithine
DescriptionN2,N5-Diacetylornithine, also known as bisorcic, belongs to the class of organic compounds known as N-acyl-L-alpha-amino acids. These are N-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N2,N5-Diacetylornithine is an N-acetyl-L-amino acid that is L-ornithine carrying two acetyl substituents at positions N-2 and N-5. N2,N5-Diacetylornithine was identified as one of forty plasma metabolites that could be used to predict gut microbiome Shannon diversity (PMID: 31477923 ). Shannon diversity is a metric that summarizes both species abundance and evenness, and it has been suggested as a marker for microbiome health.
Structure
Data?1580835652
Synonyms
ValueSource
BisorcicoChEBI
BisorcicumChEBI
N(2),N(5)-DiacetylornithineChEBI
BisorcicHMDB
N2,N5-Diacetyl-L-ornithineHMDB
N2,N5-DiacetylornithineHMDB
Chemical FormulaC9H16N2O4
Average Molecular Weight216.237
Monoisotopic Molecular Weight216.111007003
IUPAC Name(2S)-2,5-diacetamidopentanoic acid
Traditional Name(2S)-2,5-diacetamidopentanoic acid
CAS Registry Number39825-23-5
SMILES
CC(=O)NCCC[C@H](NC(C)=O)C(O)=O
InChI Identifier
InChI=1S/C9H16N2O4/c1-6(12)10-5-3-4-8(9(14)15)11-7(2)13/h8H,3-5H2,1-2H3,(H,10,12)(H,11,13)(H,14,15)/t8-/m0/s1
InChI KeyXUYANFPPYJSBPU-QMMMGPOBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-L-alpha-amino acids
Alternative Parents
Substituents
  • N-acyl-l-alpha-amino acid
  • Fatty acid
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
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
logP-1.1ALOGPS
logP-1.5ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.5 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity52.1 m³·mol⁻¹ChemAxon
Polarizability22.18 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+143.8630932474
DeepCCS[M-H]-141.50330932474
DeepCCS[M-2H]-176.76530932474
DeepCCS[M+Na]+152.11530932474
AllCCS[M+H]+149.132859911
AllCCS[M+H-H2O]+145.632859911
AllCCS[M+NH4]+152.332859911
AllCCS[M+Na]+153.232859911
AllCCS[M-H]-148.432859911
AllCCS[M+Na-2H]-149.432859911
AllCCS[M+HCOO]-150.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N2,N5-DiacetylornithineCC(=O)NCCC[C@H](NC(C)=O)C(O)=O3077.3Standard polar33892256
N2,N5-DiacetylornithineCC(=O)NCCC[C@H](NC(C)=O)C(O)=O2018.8Standard non polar33892256
N2,N5-DiacetylornithineCC(=O)NCCC[C@H](NC(C)=O)C(O)=O2080.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N2,N5-Diacetylornithine,1TMS,isomer #1CC(=O)NCCC[C@H](NC(C)=O)C(=O)O[Si](C)(C)C1938.9Semi standard non polar33892256
N2,N5-Diacetylornithine,1TMS,isomer #2CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C)C(=O)O1991.1Semi standard non polar33892256
N2,N5-Diacetylornithine,1TMS,isomer #3CC(=O)NCCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C1937.3Semi standard non polar33892256
N2,N5-Diacetylornithine,2TMS,isomer #1CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C1998.8Semi standard non polar33892256
N2,N5-Diacetylornithine,2TMS,isomer #1CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C1990.6Standard non polar33892256
N2,N5-Diacetylornithine,2TMS,isomer #1CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C2557.9Standard polar33892256
N2,N5-Diacetylornithine,2TMS,isomer #2CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C1968.6Semi standard non polar33892256
N2,N5-Diacetylornithine,2TMS,isomer #2CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C1987.5Standard non polar33892256
N2,N5-Diacetylornithine,2TMS,isomer #2CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C2467.0Standard polar33892256
N2,N5-Diacetylornithine,2TMS,isomer #3CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C1933.1Semi standard non polar33892256
N2,N5-Diacetylornithine,2TMS,isomer #3CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C2041.1Standard non polar33892256
N2,N5-Diacetylornithine,2TMS,isomer #3CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C2530.7Standard polar33892256
N2,N5-Diacetylornithine,3TMS,isomer #1CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C1954.8Semi standard non polar33892256
N2,N5-Diacetylornithine,3TMS,isomer #1CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C2046.9Standard non polar33892256
N2,N5-Diacetylornithine,3TMS,isomer #1CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C2205.0Standard polar33892256
N2,N5-Diacetylornithine,1TBDMS,isomer #1CC(=O)NCCC[C@H](NC(C)=O)C(=O)O[Si](C)(C)C(C)(C)C2203.0Semi standard non polar33892256
N2,N5-Diacetylornithine,1TBDMS,isomer #2CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)C(=O)O2217.1Semi standard non polar33892256
N2,N5-Diacetylornithine,1TBDMS,isomer #3CC(=O)NCCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C2193.6Semi standard non polar33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #1CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2467.4Semi standard non polar33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #1CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2407.2Standard non polar33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #1CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2657.7Standard polar33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #2CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C2452.3Semi standard non polar33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #2CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C2417.1Standard non polar33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #2CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C2602.7Standard polar33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #3CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2442.9Semi standard non polar33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #3CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2434.2Standard non polar33892256
N2,N5-Diacetylornithine,2TBDMS,isomer #3CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2657.4Standard polar33892256
N2,N5-Diacetylornithine,3TBDMS,isomer #1CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2661.6Semi standard non polar33892256
N2,N5-Diacetylornithine,3TBDMS,isomer #1CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2645.2Standard non polar33892256
N2,N5-Diacetylornithine,3TBDMS,isomer #1CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2590.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N2,N5-Diacetylornithine 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 - N2,N5-Diacetylornithine 10V, Negative-QTOFsplash10-014i-1290000000-6e78e276c45a4713d2772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2,N5-Diacetylornithine 20V, Negative-QTOFsplash10-0aw9-7930000000-de76aed8b20891e48b6b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2,N5-Diacetylornithine 40V, Negative-QTOFsplash10-052f-9000000000-ecdf9cccc783343733562021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2,N5-Diacetylornithine 10V, Positive-QTOFsplash10-014i-0890000000-054190e18f43372686ed2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2,N5-Diacetylornithine 20V, Positive-QTOFsplash10-0900-2900000000-fa754e72201047cf4edc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2,N5-Diacetylornithine 40V, Positive-QTOFsplash10-03di-9400000000-31a611ad836e3304367b2021-09-22Wishart 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
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (40 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedElderly (>65 years old)MaleRenal failure with dialysis details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID59375
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound65977
PDB IDNot Available
ChEBI ID133217
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. Wilmanski T, Rappaport N, Earls JC, Magis AT, Manor O, Lovejoy J, Omenn GS, Hood L, Gibbons SM, Price ND: Blood metabolome predicts gut microbiome alpha-diversity in humans. Nat Biotechnol. 2019 Oct;37(10):1217-1228. doi: 10.1038/s41587-019-0233-9. Epub 2019 Sep 2. [PubMed:31477923 ]