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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:20:02 UTC
HMDB IDHMDB0000679
Secondary Accession Numbers
  • HMDB00679
Metabolite Identification
Common NameHomocitrulline
DescriptionHomocitrulline belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Homocitrulline 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 homocitrulline a potential biomarker for the consumption of these foods. Homocitrulline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Homocitrulline.
Structure
Data?1582752149
Synonyms
ValueSource
N(6)-(Aminocarbonyl)-L-lysineChEBI
Homo-L-citrullineHMDB
L-HomocitrullineHMDB
N-e-Carbamyl-L-lysineHMDB
N-epsilon-Carbamyl-L-lysineHMDB
N6-Carbamoyl-L-lysineHMDB
N6-Carbamoyl-lysineHMDB
Ureidocaproic acidHMDB
(S)-2-Amino-6-ureidohexanoic acidHMDB
N-Ε-carbamyl-L-lysineHMDB
N6-(Aminocarbonyl)-L-lysineHMDB
HomocitrullineMeSH
Chemical FormulaC7H15N3O3
Average Molecular Weight189.2123
Monoisotopic Molecular Weight189.111341361
IUPAC Name(2S)-2-amino-6-(carbamoylamino)hexanoic acid
Traditional Namehomocitrulline
CAS Registry Number1190-49-4
SMILES
N[C@@H](CCCCNC(N)=O)C(O)=O
InChI Identifier
InChI=1S/C7H15N3O3/c8-5(6(11)12)3-1-2-4-10-7(9)13/h5H,1-4,8H2,(H,11,12)(H3,9,10,13)/t5-/m0/s1
InChI KeyXIGSAGMEBXLVJJ-YFKPBYRVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are 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 ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Carbonic acid derivative
  • Amino acid
  • Urea
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point211 - 212 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility600 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility12.1 g/LALOGPS
logP10(-3.1) g/LALOGPS
logP10(-3.5) g/LChemAxon
logS10(-1.2) g/LALOGPS
pKa (Strongest Acidic)2.35ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area118.44 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity45.93 m³·mol⁻¹ChemAxon
Polarizability19.49 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
DarkChem[M+H]+144.79131661259
DarkChem[M-H]-141.94531661259
AllCCS[M+H]+141.52932859911
AllCCS[M-H]-140.17232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HomocitrullineN[C@@H](CCCCNC(N)=O)C(O)=O2698.9Standard polar33892256
HomocitrullineN[C@@H](CCCCNC(N)=O)C(O)=O1792.4Standard non polar33892256
HomocitrullineN[C@@H](CCCCNC(N)=O)C(O)=O2277.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Homocitrulline,1TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)CCCCNC(N)=O2026.5Semi standard non polar33892256
Homocitrulline,1TMS,isomer #2C[Si](C)(C)N[C@@H](CCCCNC(N)=O)C(=O)O2084.0Semi standard non polar33892256
Homocitrulline,1TMS,isomer #3C[Si](C)(C)NC(=O)NCCCC[C@H](N)C(=O)O2121.9Semi standard non polar33892256
Homocitrulline,1TMS,isomer #4C[Si](C)(C)N(CCCC[C@H](N)C(=O)O)C(N)=O2065.3Semi standard non polar33892256
Homocitrulline,2TMS,isomer #1C[Si](C)(C)N[C@@H](CCCCNC(N)=O)C(=O)O[Si](C)(C)C2090.8Semi standard non polar33892256
Homocitrulline,2TMS,isomer #1C[Si](C)(C)N[C@@H](CCCCNC(N)=O)C(=O)O[Si](C)(C)C1941.0Standard non polar33892256
Homocitrulline,2TMS,isomer #1C[Si](C)(C)N[C@@H](CCCCNC(N)=O)C(=O)O[Si](C)(C)C3408.5Standard polar33892256
Homocitrulline,2TMS,isomer #2C[Si](C)(C)NC(=O)NCCCC[C@H](N)C(=O)O[Si](C)(C)C2110.7Semi standard non polar33892256
Homocitrulline,2TMS,isomer #2C[Si](C)(C)NC(=O)NCCCC[C@H](N)C(=O)O[Si](C)(C)C1922.1Standard non polar33892256
Homocitrulline,2TMS,isomer #2C[Si](C)(C)NC(=O)NCCCC[C@H](N)C(=O)O[Si](C)(C)C3278.8Standard polar33892256
Homocitrulline,2TMS,isomer #3C[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(N)=O)[Si](C)(C)C1970.8Semi standard non polar33892256
Homocitrulline,2TMS,isomer #3C[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(N)=O)[Si](C)(C)C1994.3Standard non polar33892256
Homocitrulline,2TMS,isomer #3C[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(N)=O)[Si](C)(C)C3525.7Standard polar33892256
Homocitrulline,2TMS,isomer #4C[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O2181.4Semi standard non polar33892256
Homocitrulline,2TMS,isomer #4C[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O1899.0Standard non polar33892256
Homocitrulline,2TMS,isomer #4C[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O3224.8Standard polar33892256
Homocitrulline,2TMS,isomer #5C[Si](C)(C)N([C@@H](CCCCNC(N)=O)C(=O)O)[Si](C)(C)C2243.6Semi standard non polar33892256
Homocitrulline,2TMS,isomer #5C[Si](C)(C)N([C@@H](CCCCNC(N)=O)C(=O)O)[Si](C)(C)C2003.4Standard non polar33892256
Homocitrulline,2TMS,isomer #5C[Si](C)(C)N([C@@H](CCCCNC(N)=O)C(=O)O)[Si](C)(C)C3584.3Standard polar33892256
Homocitrulline,2TMS,isomer #6C[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C)C(=O)O2118.6Semi standard non polar33892256
Homocitrulline,2TMS,isomer #6C[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C)C(=O)O2009.7Standard non polar33892256
Homocitrulline,2TMS,isomer #6C[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C)C(=O)O3272.6Standard polar33892256
Homocitrulline,2TMS,isomer #7C[Si](C)(C)N(C(=O)NCCCC[C@H](N)C(=O)O)[Si](C)(C)C2175.4Semi standard non polar33892256
Homocitrulline,2TMS,isomer #7C[Si](C)(C)N(C(=O)NCCCC[C@H](N)C(=O)O)[Si](C)(C)C1991.1Standard non polar33892256
Homocitrulline,2TMS,isomer #7C[Si](C)(C)N(C(=O)NCCCC[C@H](N)C(=O)O)[Si](C)(C)C3528.7Standard polar33892256
Homocitrulline,2TMS,isomer #8C[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C2116.0Semi standard non polar33892256
Homocitrulline,2TMS,isomer #8C[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C1983.9Standard non polar33892256
Homocitrulline,2TMS,isomer #8C[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C3441.4Standard polar33892256
Homocitrulline,3TMS,isomer #1C[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C2190.2Semi standard non polar33892256
Homocitrulline,3TMS,isomer #1C[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1946.9Standard non polar33892256
Homocitrulline,3TMS,isomer #1C[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C2780.1Standard polar33892256
Homocitrulline,3TMS,isomer #10C[Si](C)(C)N(CCCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C2159.8Semi standard non polar33892256
Homocitrulline,3TMS,isomer #10C[Si](C)(C)N(CCCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C2145.4Standard non polar33892256
Homocitrulline,3TMS,isomer #10C[Si](C)(C)N(CCCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C3111.1Standard polar33892256
Homocitrulline,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CCCCNC(N)=O)N([Si](C)(C)C)[Si](C)(C)C2248.2Semi standard non polar33892256
Homocitrulline,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CCCCNC(N)=O)N([Si](C)(C)C)[Si](C)(C)C2045.3Standard non polar33892256
Homocitrulline,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CCCCNC(N)=O)N([Si](C)(C)C)[Si](C)(C)C3243.0Standard polar33892256
Homocitrulline,3TMS,isomer #3C[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C2040.8Semi standard non polar33892256
Homocitrulline,3TMS,isomer #3C[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C2017.7Standard non polar33892256
Homocitrulline,3TMS,isomer #3C[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C3024.5Standard polar33892256
Homocitrulline,3TMS,isomer #4C[Si](C)(C)OC(=O)[C@@H](N)CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C2120.1Semi standard non polar33892256
Homocitrulline,3TMS,isomer #4C[Si](C)(C)OC(=O)[C@@H](N)CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C2072.1Standard non polar33892256
Homocitrulline,3TMS,isomer #4C[Si](C)(C)OC(=O)[C@@H](N)CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C2995.3Standard polar33892256
Homocitrulline,3TMS,isomer #5C[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C2058.0Semi standard non polar33892256
Homocitrulline,3TMS,isomer #5C[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C2034.2Standard non polar33892256
Homocitrulline,3TMS,isomer #5C[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C2964.6Standard polar33892256
Homocitrulline,3TMS,isomer #6C[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2219.4Semi standard non polar33892256
Homocitrulline,3TMS,isomer #6C[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2053.9Standard non polar33892256
Homocitrulline,3TMS,isomer #6C[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2819.2Standard polar33892256
Homocitrulline,3TMS,isomer #7C[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C2165.5Semi standard non polar33892256
Homocitrulline,3TMS,isomer #7C[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C2042.3Standard non polar33892256
Homocitrulline,3TMS,isomer #7C[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C2796.7Standard polar33892256
Homocitrulline,3TMS,isomer #8C[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2334.2Semi standard non polar33892256
Homocitrulline,3TMS,isomer #8C[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1992.3Standard non polar33892256
Homocitrulline,3TMS,isomer #8C[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2906.4Standard polar33892256
Homocitrulline,3TMS,isomer #9C[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(N)=O2212.6Semi standard non polar33892256
Homocitrulline,3TMS,isomer #9C[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(N)=O2101.7Standard non polar33892256
Homocitrulline,3TMS,isomer #9C[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(N)=O3118.4Standard polar33892256
Homocitrulline,4TMS,isomer #1C[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2162.8Semi standard non polar33892256
Homocitrulline,4TMS,isomer #1C[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2104.3Standard non polar33892256
Homocitrulline,4TMS,isomer #1C[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2482.2Standard polar33892256
Homocitrulline,4TMS,isomer #2C[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C2124.2Semi standard non polar33892256
Homocitrulline,4TMS,isomer #2C[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C2057.4Standard non polar33892256
Homocitrulline,4TMS,isomer #2C[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C2451.0Standard polar33892256
Homocitrulline,4TMS,isomer #3C[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2331.6Semi standard non polar33892256
Homocitrulline,4TMS,isomer #3C[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2037.1Standard non polar33892256
Homocitrulline,4TMS,isomer #3C[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2597.5Standard polar33892256
Homocitrulline,4TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](CCCCN(C(N)=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2213.7Semi standard non polar33892256
Homocitrulline,4TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](CCCCN(C(N)=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2118.6Standard non polar33892256
Homocitrulline,4TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](CCCCN(C(N)=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2951.6Standard polar33892256
Homocitrulline,4TMS,isomer #5C[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2131.5Semi standard non polar33892256
Homocitrulline,4TMS,isomer #5C[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2199.7Standard non polar33892256
Homocitrulline,4TMS,isomer #5C[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2702.3Standard polar33892256
Homocitrulline,4TMS,isomer #6C[Si](C)(C)N(C(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2346.0Semi standard non polar33892256
Homocitrulline,4TMS,isomer #6C[Si](C)(C)N(C(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2162.8Standard non polar33892256
Homocitrulline,4TMS,isomer #6C[Si](C)(C)N(C(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2608.8Standard polar33892256
Homocitrulline,4TMS,isomer #7C[Si](C)(C)N[C@@H](CCCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O2219.4Semi standard non polar33892256
Homocitrulline,4TMS,isomer #7C[Si](C)(C)N[C@@H](CCCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O2217.4Standard non polar33892256
Homocitrulline,4TMS,isomer #7C[Si](C)(C)N[C@@H](CCCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O2483.6Standard polar33892256
Homocitrulline,4TMS,isomer #8C[Si](C)(C)NC(=O)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2285.8Semi standard non polar33892256
Homocitrulline,4TMS,isomer #8C[Si](C)(C)NC(=O)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2142.9Standard non polar33892256
Homocitrulline,4TMS,isomer #8C[Si](C)(C)NC(=O)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2585.4Standard polar33892256
Homocitrulline,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2376.0Semi standard non polar33892256
Homocitrulline,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2192.9Standard non polar33892256
Homocitrulline,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2357.3Standard polar33892256
Homocitrulline,5TMS,isomer #2C[Si](C)(C)N[C@@H](CCCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2188.5Semi standard non polar33892256
Homocitrulline,5TMS,isomer #2C[Si](C)(C)N[C@@H](CCCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2243.0Standard non polar33892256
Homocitrulline,5TMS,isomer #2C[Si](C)(C)N[C@@H](CCCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2203.3Standard polar33892256
Homocitrulline,5TMS,isomer #3C[Si](C)(C)NC(=O)N(CCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2330.9Semi standard non polar33892256
Homocitrulline,5TMS,isomer #3C[Si](C)(C)NC(=O)N(CCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2156.8Standard non polar33892256
Homocitrulline,5TMS,isomer #3C[Si](C)(C)NC(=O)N(CCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2343.4Standard polar33892256
Homocitrulline,5TMS,isomer #4C[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N([Si](C)(C)C)[Si](C)(C)C2365.0Semi standard non polar33892256
Homocitrulline,5TMS,isomer #4C[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N([Si](C)(C)C)[Si](C)(C)C2334.8Standard non polar33892256
Homocitrulline,5TMS,isomer #4C[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N([Si](C)(C)C)[Si](C)(C)C2331.3Standard polar33892256
Homocitrulline,6TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CCCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2431.2Semi standard non polar33892256
Homocitrulline,6TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CCCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2337.9Standard non polar33892256
Homocitrulline,6TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CCCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2166.4Standard polar33892256
Homocitrulline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCNC(N)=O2275.9Semi standard non polar33892256
Homocitrulline,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CCCCNC(N)=O)C(=O)O2342.5Semi standard non polar33892256
Homocitrulline,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N)C(=O)O2355.5Semi standard non polar33892256
Homocitrulline,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(CCCC[C@H](N)C(=O)O)C(N)=O2282.5Semi standard non polar33892256
Homocitrulline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCCNC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C2561.2Semi standard non polar33892256
Homocitrulline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCCNC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C2357.2Standard non polar33892256
Homocitrulline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCCNC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C3333.9Standard polar33892256
Homocitrulline,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C2590.6Semi standard non polar33892256
Homocitrulline,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C2340.1Standard non polar33892256
Homocitrulline,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C3182.3Standard polar33892256
Homocitrulline,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C2451.7Semi standard non polar33892256
Homocitrulline,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C2404.3Standard non polar33892256
Homocitrulline,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C3508.6Standard polar33892256
Homocitrulline,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O2691.7Semi standard non polar33892256
Homocitrulline,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O2331.1Standard non polar33892256
Homocitrulline,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O3056.0Standard polar33892256
Homocitrulline,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N([C@@H](CCCCNC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C2683.0Semi standard non polar33892256
Homocitrulline,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N([C@@H](CCCCNC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C2411.3Standard non polar33892256
Homocitrulline,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N([C@@H](CCCCNC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C3434.7Standard polar33892256
Homocitrulline,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O2591.4Semi standard non polar33892256
Homocitrulline,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O2437.2Standard non polar33892256
Homocitrulline,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O3248.0Standard polar33892256
Homocitrulline,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(C(=O)NCCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C2619.6Semi standard non polar33892256
Homocitrulline,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(C(=O)NCCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C2429.6Standard non polar33892256
Homocitrulline,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(C(=O)NCCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C3332.5Standard polar33892256
Homocitrulline,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C2583.2Semi standard non polar33892256
Homocitrulline,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C2413.4Standard non polar33892256
Homocitrulline,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C3302.1Standard polar33892256
Homocitrulline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2872.4Semi standard non polar33892256
Homocitrulline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2496.1Standard non polar33892256
Homocitrulline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2846.1Standard polar33892256
Homocitrulline,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)N(CCCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2818.2Semi standard non polar33892256
Homocitrulline,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)N(CCCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2708.2Standard non polar33892256
Homocitrulline,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)N(CCCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3083.7Standard polar33892256
Homocitrulline,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCNC(N)=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2891.3Semi standard non polar33892256
Homocitrulline,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCNC(N)=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2641.8Standard non polar33892256
Homocitrulline,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCNC(N)=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3209.5Standard polar33892256
Homocitrulline,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2726.1Semi standard non polar33892256
Homocitrulline,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2595.1Standard non polar33892256
Homocitrulline,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3125.6Standard polar33892256
Homocitrulline,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2799.0Semi standard non polar33892256
Homocitrulline,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2659.4Standard non polar33892256
Homocitrulline,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3013.4Standard polar33892256
Homocitrulline,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2734.9Semi standard non polar33892256
Homocitrulline,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2615.7Standard non polar33892256
Homocitrulline,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3032.4Standard polar33892256
Homocitrulline,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2922.3Semi standard non polar33892256
Homocitrulline,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2638.5Standard non polar33892256
Homocitrulline,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2885.9Standard polar33892256
Homocitrulline,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2869.4Semi standard non polar33892256
Homocitrulline,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2611.9Standard non polar33892256
Homocitrulline,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2901.9Standard polar33892256
Homocitrulline,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2976.8Semi standard non polar33892256
Homocitrulline,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2567.3Standard non polar33892256
Homocitrulline,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2922.8Standard polar33892256
Homocitrulline,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(N)=O2863.1Semi standard non polar33892256
Homocitrulline,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(N)=O2658.3Standard non polar33892256
Homocitrulline,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(N)=O3167.0Standard polar33892256
Homocitrulline,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3054.9Semi standard non polar33892256
Homocitrulline,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2806.6Standard non polar33892256
Homocitrulline,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2779.4Standard polar33892256
Homocitrulline,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3006.6Semi standard non polar33892256
Homocitrulline,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2756.5Standard non polar33892256
Homocitrulline,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2806.4Standard polar33892256
Homocitrulline,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3169.6Semi standard non polar33892256
Homocitrulline,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2743.7Standard non polar33892256
Homocitrulline,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2847.4Standard polar33892256
Homocitrulline,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3093.7Semi standard non polar33892256
Homocitrulline,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2829.9Standard non polar33892256
Homocitrulline,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3139.4Standard polar33892256
Homocitrulline,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2998.8Semi standard non polar33892256
Homocitrulline,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2895.4Standard non polar33892256
Homocitrulline,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2932.1Standard polar33892256
Homocitrulline,4TBDMS,isomer #6CC(C)(C)[Si](C)(C)N(C(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3205.0Semi standard non polar33892256
Homocitrulline,4TBDMS,isomer #6CC(C)(C)[Si](C)(C)N(C(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2876.2Standard non polar33892256
Homocitrulline,4TBDMS,isomer #6CC(C)(C)[Si](C)(C)N(C(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2833.1Standard polar33892256
Homocitrulline,4TBDMS,isomer #7CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O3101.6Semi standard non polar33892256
Homocitrulline,4TBDMS,isomer #7CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2893.9Standard non polar33892256
Homocitrulline,4TBDMS,isomer #7CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2815.1Standard polar33892256
Homocitrulline,4TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3123.7Semi standard non polar33892256
Homocitrulline,4TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2830.4Standard non polar33892256
Homocitrulline,4TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2867.3Standard polar33892256
Homocitrulline,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3404.1Semi standard non polar33892256
Homocitrulline,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3041.5Standard non polar33892256
Homocitrulline,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2765.8Standard polar33892256
Homocitrulline,5TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3262.9Semi standard non polar33892256
Homocitrulline,5TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3052.6Standard non polar33892256
Homocitrulline,5TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2738.9Standard polar33892256
Homocitrulline,5TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3366.7Semi standard non polar33892256
Homocitrulline,5TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3002.0Standard non polar33892256
Homocitrulline,5TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2804.0Standard polar33892256
Homocitrulline,5TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3387.0Semi standard non polar33892256
Homocitrulline,5TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3119.9Standard non polar33892256
Homocitrulline,5TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2774.8Standard polar33892256
Homocitrulline,6TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3604.8Semi standard non polar33892256
Homocitrulline,6TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3297.7Standard non polar33892256
Homocitrulline,6TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2784.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Homocitrulline GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-0900000000-74fcbf67e1025457671a2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Homocitrulline GC-EI-TOF (Non-derivatized)splash10-00di-0900000000-74fcbf67e1025457671a2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homocitrulline GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9100000000-560475aa29e1d94e59aa2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homocitrulline GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9700000000-ef60915445de08613bb12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homocitrulline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homocitrulline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homocitrulline GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homocitrulline GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homocitrulline GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homocitrulline GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homocitrulline GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homocitrulline GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Homocitrulline GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00di-1900000000-adcca2902e0538d46b162012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001i-9200000000-1fb814f74322670c53a22012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-053r-9000000000-0940c0b18cf743baf3672012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline 30V, Positive-QTOFsplash10-001i-9100000000-cc77b5afd311cbae0fa82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline 40V, Positive-QTOFsplash10-053r-9000000000-a0189e6f8078c6ffa5202021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline 20V, Negative-QTOFsplash10-0002-9300000000-ece511f06e8ad89964562021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline 40V, Negative-QTOFsplash10-054k-9000000000-6fc6f1f7981d8d290c042021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline 0V, Positive-QTOFsplash10-01ox-2930000000-fb8aea8c8cb6fa1f69802021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline 10V, Negative-QTOFsplash10-0005-4900000000-9d6c42dcd46ed350e0d62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline 40V, Negative-QTOFsplash10-0006-9000000000-28a7ec59b0224b2b10442021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline 10V, Positive-QTOFsplash10-0pir-8900000000-ebaf5608fe25e11a4a6f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline 30V, Positive-QTOFsplash10-0a4i-9000000000-766ff7efc90e65dc3cc42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline 20V, Negative-QTOFsplash10-0002-1900000000-4a46de28055906c905e42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline 30V, Negative-QTOFsplash10-0005-7900000000-cf282e5450dc67e5a74e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline 0V, Positive-QTOFsplash10-01ox-1950000000-5b126d209e94f7a29c4e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline 20V, Positive-QTOFsplash10-003r-9600000000-8bc13bf563ece5c338742021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline 10V, Positive-QTOFsplash10-00b9-1900000000-db388565404b40f99df52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline 40V, Positive-QTOFsplash10-0a59-9000000000-c3763a240b1b1a1329f52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Homocitrulline 10V, Positive-QTOFsplash10-00fr-1900000000-853bd3fba3289e99c3422021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocitrulline 10V, Positive-QTOFsplash10-006y-0900000000-8e7e33c59412f835b2c52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocitrulline 20V, Positive-QTOFsplash10-0fam-4900000000-32c82cff8160c02dccef2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocitrulline 40V, Positive-QTOFsplash10-001i-9000000000-ce7fde8e34720158c0b22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocitrulline 10V, Negative-QTOFsplash10-002n-3900000000-9f2e58f8c995982ec6ad2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocitrulline 20V, Negative-QTOFsplash10-002e-4900000000-5bdd3f534ea48aaaccb72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Homocitrulline 40V, Negative-QTOFsplash10-0006-9000000000-04f0b7eb9d2e035a6fa22017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified5.0 (0.0-12.0) uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified<7.013 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified0 - 10.18 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 10.18 umol/mmol creatinineInfant (1 - 6 months old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 10.18 umol/mmol creatinineInfant (6 months - <1 year old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 10.18 umol/mmol creatinineChildren (1 - 2 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 10.18 umol/mmol creatinineChildren (2 - 4 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 10.18 umol/mmol creatinineChildren (4 - 13 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 10.18 umol/mmol creatinineAdolescent (13 - 21 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0 - 10.18 umol/mmol creatinineAdult (>21 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified6.0 (0-8.8) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified<3.73 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal details
UrineDetected and Quantified<3.39 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified<33.36 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified1.24-17.87 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified7.5 (3.8-13.8) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified<8.031 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified11.998 +/- 9.054 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified63-83 umol/mmol creatinineChildren (1-13 years old)BothHyperlysinemia I, familial details
UrineDetected and Quantified8.359 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Hyperlysinemia I, familial
  1. Tondo M, Calpena E, Arriola G, Sanz P, Martorell L, Ormazabal A, Castejon E, Palacin M, Ugarte M, Espinos C, Perez B, Perez-Duenas B, Perez-Cerda C, Artuch R: Clinical, biochemical, molecular and therapeutic aspects of 2 new cases of 2-aminoadipic semialdehyde synthase deficiency. Mol Genet Metab. 2013 Nov;110(3):231-6. doi: 10.1016/j.ymgme.2013.06.021. Epub 2013 Jul 6. [PubMed:23890588 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022178
KNApSAcK IDC00052314
Chemspider ID58582
KEGG Compound IDC02427
BioCyc IDCPD-161
BiGG IDNot Available
Wikipedia LinkHomocitrulline
METLIN ID46
PubChem Compound65072
PDB IDNot Available
ChEBI ID17443
Food Biomarker OntologyNot Available
VMH IDHMCR
MarkerDB IDMDB00029987
Good Scents IDNot Available
References
Synthesis ReferenceStark, George R. Reactions of cyanate with functional groups of proteins. III. Reactions with amino and carboxyl groups. Biochemistry (1965), 4(6), 1030-6.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kato T, Sano M, Mizutani N: Inhibitory effect of intravenous lysine infusion on urea cycle metabolism. Eur J Pediatr. 1987 Jan;146(1):56-8. [PubMed:3107993 ]
  2. Tuchman M, Knopman DS, Shih VE: Episodic hyperammonemia in adult siblings with hyperornithinemia, hyperammonemia, and homocitrullinuria syndrome. Arch Neurol. 1990 Oct;47(10):1134-7. [PubMed:2222247 ]
  3. Rajantie J, Simell O, Perheentupa J: Oral administration of epsilon N-acetyllysine and homocitrulline in lysinuric protein intolerance. J Pediatr. 1983 Mar;102(3):388-90. [PubMed:6402575 ]
  4. Dionisi Vici C, Bachmann C, Gambarara M, Colombo JP, Sabetta G: Hyperornithinemia-hyperammonemia-homocitrullinuria syndrome: low creatine excretion and effect of citrulline, arginine, or ornithine supplement. Pediatr Res. 1987 Sep;22(3):364-7. [PubMed:3116497 ]
  5. Hommes FA, Roesel RA, Metoki K, Hartlage PL, Dyken PR: Studies on a case of HHH-syndrome (hyperammonemia, hyperornithinemia, homocitrullinuria). Neuropediatrics. 1986 Feb;17(1):48-52. [PubMed:3960284 ]
  6. Koshiishi I, Kobori Y, Imanari T: Determination of citrulline and homocitrulline by high-performance liquid chromatography with post-column derivatization. J Chromatogr. 1990 Oct 26;532(1):37-43. [PubMed:2079537 ]
  7. Evered DF, Vadgama JV: Absorption of homocitrulline from the gastrointestinal tract. Br J Nutr. 1983 Jan;49(1):35-42. [PubMed:6821687 ]
  8. Kato T, Sano M, Mizutani N, Hayakawa C: Homocitrullinuria and homoargininuria in hyperargininaemia. J Inherit Metab Dis. 1988;11(3):261-5. [PubMed:2466169 ]
  9. Kato T, Sano M: Effect of ammonium chloride on homocitrulline and homoarginine synthesis from lysine. J Inherit Metab Dis. 1993;16(5):906-7. [PubMed:7507534 ]
  10. Kato T, Sano M, Mizutani N: Homocitrullinuria and homoargininuria in lysinuric protein intolerance. J Inherit Metab Dis. 1989;12(2):157-61. [PubMed:2474087 ]
  11. Zammarchi E, Donati MA, Filippi L, Resti M: Cryptogenic hepatitis masking the diagnosis of ornithine transcarbamylase deficiency. J Pediatr Gastroenterol Nutr. 1996 May;22(4):380-3. [PubMed:8732901 ]
  12. Simell O, Mackenzie S, Clow CL, Scriver CR: Ornithine loading did not prevent induced hyperammonemia in a patient with hyperornithinemia-hyperammonemia-homocitrullinuria syndrome. Pediatr Res. 1985 Dec;19(12):1283-7. [PubMed:4080446 ]
  13. Kraus LM, Gaber L, Handorf CR, Marti HP, Kraus AP Jr: Carbamoylation of glomerular and tubular proteins in patients with kidney failure: a potential mechanism of ongoing renal damage. Swiss Med Wkly. 2001 Mar 24;131(11-12):139-4. [PubMed:11416886 ]
  14. Kraus LM, Elberger AJ, Handorf CR, Pabst MJ, Kraus AP Jr: Urea-derived cyanate forms epsilon-amino-carbamoyl-lysine (homocitrulline) in leukocyte proteins in patients with end-stage renal disease on peritoneal dialysis. J Lab Clin Med. 1994 Jun;123(6):882-91. [PubMed:8201267 ]
  15. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]