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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:55:58 UTC

HMDB ID

HMDB0000679

Secondary Accession Numbers

HMDB00679

Metabolite Identification

Common Name

Homocitrulline

Description

Homocitrulline 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 01-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-NOV-19         0                                  
HETATM    1  C   UNK     0    8685.0178682.603   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8686.3528683.373   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8687.6848682.603   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8689.0208683.373   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8687.6848681.063   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0    8686.3528684.912   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0    8683.6818683.373   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8682.3488682.603   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8681.0148683.373   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0    8679.6798682.603   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    8678.3458683.373   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8677.0118682.603   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0    8678.3458684.912   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

COMPND    HMDB0000679
HETATM    1  N1  UNL     1       4.190   0.983  -1.094  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.863   0.546  -0.806  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.958   1.403  -0.956  1.00  0.00           O  
HETATM    4  N2  UNL     1       2.619  -0.784  -0.377  1.00  0.00           N  
HETATM    5  C2  UNL     1       1.282  -1.248  -0.078  1.00  0.00           C  
HETATM    6  C3  UNL     1       0.683  -0.437   1.034  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.702  -0.859   1.400  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.692  -0.763   0.287  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.787   0.669  -0.195  1.00  0.00           C  
HETATM   10  N3  UNL     1      -2.208   1.474   0.911  1.00  0.00           N  
HETATM   11  C7  UNL     1      -2.699   0.808  -1.351  1.00  0.00           C  
HETATM   12  O2  UNL     1      -3.686   1.578  -1.230  1.00  0.00           O  
HETATM   13  O3  UNL     1      -2.532   0.147  -2.545  1.00  0.00           O  
HETATM   14  H1  UNL     1       4.992   0.458  -0.673  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.399   1.790  -1.696  1.00  0.00           H  
HETATM   16  H3  UNL     1       3.428  -1.433  -0.279  1.00  0.00           H  
HETATM   17  H4  UNL     1       0.677  -1.065  -1.013  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.280  -2.320   0.100  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.688   0.635   0.832  1.00  0.00           H  
HETATM   20  H7  UNL     1       1.311  -0.586   1.962  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.710  -1.887   1.831  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.038  -0.194   2.234  1.00  0.00           H  
HETATM   23  H10 UNL     1      -1.475  -1.407  -0.567  1.00  0.00           H  
HETATM   24  H11 UNL     1      -2.699  -1.035   0.664  1.00  0.00           H  
HETATM   25  H12 UNL     1      -0.788   0.981  -0.524  1.00  0.00           H  
HETATM   26  H13 UNL     1      -2.635   0.967   1.693  1.00  0.00           H  
HETATM   27  H14 UNL     1      -2.742   2.319   0.628  1.00  0.00           H  
HETATM   28  H15 UNL     1      -2.975  -0.741  -2.777  1.00  0.00           H  
CONECT    1    2   14   15
CONECT    2    3    3    4
CONECT    4    5   16
CONECT    5    6   17   18
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9   23   24
CONECT    9   10   11   25
CONECT   10   26   27
CONECT   11   12   12   13
CONECT   13   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N(6)-(Aminocarbonyl)-L-lysine	ChEBI
Homo-L-citrulline	HMDB
L-Homocitrulline	HMDB
N-e-Carbamyl-L-lysine	HMDB
N-epsilon-Carbamyl-L-lysine	HMDB
N6-Carbamoyl-L-lysine	HMDB
N6-Carbamoyl-lysine	HMDB
Ureidocaproic acid	HMDB
(S)-2-Amino-6-ureidohexanoic acid	HMDB
N-Ε-carbamyl-L-lysine	HMDB
N6-(Aminocarbonyl)-L-lysine	HMDB
Homocitrulline	MeSH

Chemical Formula

C₇H₁₅N₃O₃

Average Molecular Weight

189.2123

Monoisotopic Molecular Weight

189.111341361

IUPAC Name

(2S)-2-amino-6-(carbamoylamino)hexanoic acid

Traditional Name

homocitrulline

CAS Registry Number

1190-49-4

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 Key

XIGSAGMEBXLVJJ-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-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 Framework

Aliphatic acyclic compounds

External Descriptors

ureas (CHEBI:17443 )
non-proteinogenic L-alpha-amino acid (CHEBI:17443 )
L-lysine derivative (CHEBI:17443 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000679)

Organ

Placenta (HMDB: HMDB0000679)

Excreta

Biofluid or Excreta

Urine (PMID: 17053917)
Feces (PMID: 27543620)

Cellular substructure

Cytoplasm (HMDB: HMDB0000679)
Membrane (HMDB: HMDB0000679)

Source

Endogenous

Endogenous (HMDB: HMDB0000679)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome] (HMDB: HMDB0000679)

Role

Biological role

Human metabolite (HMDB: HMDB0000679)
Mouse metabolite (HMDB: HMDB0000679)

Industrial application

Pharmaceutical industry

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00029987)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	211 - 212 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	600 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12.1 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-3.5	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	2.35	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	118.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	45.93 m³·mol⁻¹	ChemAxon
Polarizability	19.49 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	144.791	31661259
DarkChem	[M-H]-	141.945	31661259
AllCCS	[M+H]+	141.529	32859911
AllCCS	[M-H]-	140.172	32859911
DeepCCS	[M+H]+	139.758	30932474
DeepCCS	[M-H]-	136.108	30932474
DeepCCS	[M-2H]-	173.707	30932474
DeepCCS	[M+Na]+	149.246	30932474
AllCCS	[M+H]+	141.5	32859911
AllCCS	[M+H-H2O]+	137.9	32859911
AllCCS	[M+NH4]+	144.9	32859911
AllCCS	[M+Na]+	145.9	32859911
AllCCS	[M-H]-	140.2	32859911
AllCCS	[M+Na-2H]-	141.4	32859911
AllCCS	[M+HCOO]-	142.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Homocitrulline	N[C@@H](CCCCNC(N)=O)C(O)=O	2698.9	Standard polar	33892256
Homocitrulline	N[C@@H](CCCCNC(N)=O)C(O)=O	1792.4	Standard non polar	33892256
Homocitrulline	N[C@@H](CCCCNC(N)=O)C(O)=O	2277.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Homocitrulline,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CCCCNC(N)=O	2026.5	Semi standard non polar	33892256
Homocitrulline,1TMS,isomer #2	C[Si](C)(C)N[C@@H](CCCCNC(N)=O)C(=O)O	2084.0	Semi standard non polar	33892256
Homocitrulline,1TMS,isomer #3	C[Si](C)(C)NC(=O)NCCCC[C@H](N)C(=O)O	2121.9	Semi standard non polar	33892256
Homocitrulline,1TMS,isomer #4	C[Si](C)(C)N(CCCC[C@H](N)C(=O)O)C(N)=O	2065.3	Semi standard non polar	33892256
Homocitrulline,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CCCCNC(N)=O)C(=O)O[Si](C)(C)C	2090.8	Semi standard non polar	33892256
Homocitrulline,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CCCCNC(N)=O)C(=O)O[Si](C)(C)C	1941.0	Standard non polar	33892256
Homocitrulline,2TMS,isomer #1	C[Si](C)(C)N[C@@H](CCCCNC(N)=O)C(=O)O[Si](C)(C)C	3408.5	Standard polar	33892256
Homocitrulline,2TMS,isomer #2	C[Si](C)(C)NC(=O)NCCCC[C@H](N)C(=O)O[Si](C)(C)C	2110.7	Semi standard non polar	33892256
Homocitrulline,2TMS,isomer #2	C[Si](C)(C)NC(=O)NCCCC[C@H](N)C(=O)O[Si](C)(C)C	1922.1	Standard non polar	33892256
Homocitrulline,2TMS,isomer #2	C[Si](C)(C)NC(=O)NCCCC[C@H](N)C(=O)O[Si](C)(C)C	3278.8	Standard polar	33892256
Homocitrulline,2TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(N)=O)[Si](C)(C)C	1970.8	Semi standard non polar	33892256
Homocitrulline,2TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(N)=O)[Si](C)(C)C	1994.3	Standard non polar	33892256
Homocitrulline,2TMS,isomer #3	C[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(N)=O)[Si](C)(C)C	3525.7	Standard polar	33892256
Homocitrulline,2TMS,isomer #4	C[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O	2181.4	Semi standard non polar	33892256
Homocitrulline,2TMS,isomer #4	C[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O	1899.0	Standard non polar	33892256
Homocitrulline,2TMS,isomer #4	C[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O	3224.8	Standard polar	33892256
Homocitrulline,2TMS,isomer #5	C[Si](C)(C)N([C@@H](CCCCNC(N)=O)C(=O)O)[Si](C)(C)C	2243.6	Semi standard non polar	33892256
Homocitrulline,2TMS,isomer #5	C[Si](C)(C)N([C@@H](CCCCNC(N)=O)C(=O)O)[Si](C)(C)C	2003.4	Standard non polar	33892256
Homocitrulline,2TMS,isomer #5	C[Si](C)(C)N([C@@H](CCCCNC(N)=O)C(=O)O)[Si](C)(C)C	3584.3	Standard polar	33892256
Homocitrulline,2TMS,isomer #6	C[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C)C(=O)O	2118.6	Semi standard non polar	33892256
Homocitrulline,2TMS,isomer #6	C[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C)C(=O)O	2009.7	Standard non polar	33892256
Homocitrulline,2TMS,isomer #6	C[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C)C(=O)O	3272.6	Standard polar	33892256
Homocitrulline,2TMS,isomer #7	C[Si](C)(C)N(C(=O)NCCCC[C@H](N)C(=O)O)[Si](C)(C)C	2175.4	Semi standard non polar	33892256
Homocitrulline,2TMS,isomer #7	C[Si](C)(C)N(C(=O)NCCCC[C@H](N)C(=O)O)[Si](C)(C)C	1991.1	Standard non polar	33892256
Homocitrulline,2TMS,isomer #7	C[Si](C)(C)N(C(=O)NCCCC[C@H](N)C(=O)O)[Si](C)(C)C	3528.7	Standard polar	33892256
Homocitrulline,2TMS,isomer #8	C[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C	2116.0	Semi standard non polar	33892256
Homocitrulline,2TMS,isomer #8	C[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C	1983.9	Standard non polar	33892256
Homocitrulline,2TMS,isomer #8	C[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C	3441.4	Standard polar	33892256
Homocitrulline,3TMS,isomer #1	C[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2190.2	Semi standard non polar	33892256
Homocitrulline,3TMS,isomer #1	C[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1946.9	Standard non polar	33892256
Homocitrulline,3TMS,isomer #1	C[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2780.1	Standard polar	33892256
Homocitrulline,3TMS,isomer #10	C[Si](C)(C)N(CCCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	2159.8	Semi standard non polar	33892256
Homocitrulline,3TMS,isomer #10	C[Si](C)(C)N(CCCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	2145.4	Standard non polar	33892256
Homocitrulline,3TMS,isomer #10	C[Si](C)(C)N(CCCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C	3111.1	Standard polar	33892256
Homocitrulline,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CCCCNC(N)=O)N([Si](C)(C)C)[Si](C)(C)C	2248.2	Semi standard non polar	33892256
Homocitrulline,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CCCCNC(N)=O)N([Si](C)(C)C)[Si](C)(C)C	2045.3	Standard non polar	33892256
Homocitrulline,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](CCCCNC(N)=O)N([Si](C)(C)C)[Si](C)(C)C	3243.0	Standard polar	33892256
Homocitrulline,3TMS,isomer #3	C[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2040.8	Semi standard non polar	33892256
Homocitrulline,3TMS,isomer #3	C[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2017.7	Standard non polar	33892256
Homocitrulline,3TMS,isomer #3	C[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C	3024.5	Standard polar	33892256
Homocitrulline,3TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H](N)CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C	2120.1	Semi standard non polar	33892256
Homocitrulline,3TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H](N)CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C	2072.1	Standard non polar	33892256
Homocitrulline,3TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H](N)CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C	2995.3	Standard polar	33892256
Homocitrulline,3TMS,isomer #5	C[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2058.0	Semi standard non polar	33892256
Homocitrulline,3TMS,isomer #5	C[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2034.2	Standard non polar	33892256
Homocitrulline,3TMS,isomer #5	C[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2964.6	Standard polar	33892256
Homocitrulline,3TMS,isomer #6	C[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2219.4	Semi standard non polar	33892256
Homocitrulline,3TMS,isomer #6	C[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2053.9	Standard non polar	33892256
Homocitrulline,3TMS,isomer #6	C[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2819.2	Standard polar	33892256
Homocitrulline,3TMS,isomer #7	C[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2165.5	Semi standard non polar	33892256
Homocitrulline,3TMS,isomer #7	C[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2042.3	Standard non polar	33892256
Homocitrulline,3TMS,isomer #7	C[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2796.7	Standard polar	33892256
Homocitrulline,3TMS,isomer #8	C[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2334.2	Semi standard non polar	33892256
Homocitrulline,3TMS,isomer #8	C[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1992.3	Standard non polar	33892256
Homocitrulline,3TMS,isomer #8	C[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2906.4	Standard polar	33892256
Homocitrulline,3TMS,isomer #9	C[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(N)=O	2212.6	Semi standard non polar	33892256
Homocitrulline,3TMS,isomer #9	C[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(N)=O	2101.7	Standard non polar	33892256
Homocitrulline,3TMS,isomer #9	C[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(N)=O	3118.4	Standard polar	33892256
Homocitrulline,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2162.8	Semi standard non polar	33892256
Homocitrulline,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2104.3	Standard non polar	33892256
Homocitrulline,4TMS,isomer #1	C[Si](C)(C)N[C@@H](CCCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2482.2	Standard polar	33892256
Homocitrulline,4TMS,isomer #2	C[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2124.2	Semi standard non polar	33892256
Homocitrulline,4TMS,isomer #2	C[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2057.4	Standard non polar	33892256
Homocitrulline,4TMS,isomer #2	C[Si](C)(C)NC(=O)N(CCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2451.0	Standard polar	33892256
Homocitrulline,4TMS,isomer #3	C[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2331.6	Semi standard non polar	33892256
Homocitrulline,4TMS,isomer #3	C[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2037.1	Standard non polar	33892256
Homocitrulline,4TMS,isomer #3	C[Si](C)(C)NC(=O)NCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2597.5	Standard polar	33892256
Homocitrulline,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CCCCN(C(N)=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2213.7	Semi standard non polar	33892256
Homocitrulline,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CCCCN(C(N)=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2118.6	Standard non polar	33892256
Homocitrulline,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](CCCCN(C(N)=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2951.6	Standard polar	33892256
Homocitrulline,4TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2131.5	Semi standard non polar	33892256
Homocitrulline,4TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2199.7	Standard non polar	33892256
Homocitrulline,4TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2702.3	Standard polar	33892256
Homocitrulline,4TMS,isomer #6	C[Si](C)(C)N(C(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2346.0	Semi standard non polar	33892256
Homocitrulline,4TMS,isomer #6	C[Si](C)(C)N(C(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2162.8	Standard non polar	33892256
Homocitrulline,4TMS,isomer #6	C[Si](C)(C)N(C(=O)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2608.8	Standard polar	33892256
Homocitrulline,4TMS,isomer #7	C[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	2219.4	Semi standard non polar	33892256
Homocitrulline,4TMS,isomer #7	C[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	2217.4	Standard non polar	33892256
Homocitrulline,4TMS,isomer #7	C[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	2483.6	Standard polar	33892256
Homocitrulline,4TMS,isomer #8	C[Si](C)(C)NC(=O)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2285.8	Semi standard non polar	33892256
Homocitrulline,4TMS,isomer #8	C[Si](C)(C)NC(=O)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2142.9	Standard non polar	33892256
Homocitrulline,4TMS,isomer #8	C[Si](C)(C)NC(=O)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2585.4	Standard polar	33892256
Homocitrulline,5TMS,isomer #1	C[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)C	2376.0	Semi standard non polar	33892256
Homocitrulline,5TMS,isomer #1	C[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)C	2192.9	Standard non polar	33892256
Homocitrulline,5TMS,isomer #1	C[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)C	2357.3	Standard polar	33892256
Homocitrulline,5TMS,isomer #2	C[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)C	2188.5	Semi standard non polar	33892256
Homocitrulline,5TMS,isomer #2	C[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)C	2243.0	Standard non polar	33892256
Homocitrulline,5TMS,isomer #2	C[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)C	2203.3	Standard polar	33892256
Homocitrulline,5TMS,isomer #3	C[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)C	2330.9	Semi standard non polar	33892256
Homocitrulline,5TMS,isomer #3	C[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)C	2156.8	Standard non polar	33892256
Homocitrulline,5TMS,isomer #3	C[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)C	2343.4	Standard polar	33892256
Homocitrulline,5TMS,isomer #4	C[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)C	2365.0	Semi standard non polar	33892256
Homocitrulline,5TMS,isomer #4	C[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)C	2334.8	Standard non polar	33892256
Homocitrulline,5TMS,isomer #4	C[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)C	2331.3	Standard polar	33892256
Homocitrulline,6TMS,isomer #1	C[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)C	2431.2	Semi standard non polar	33892256
Homocitrulline,6TMS,isomer #1	C[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)C	2337.9	Standard non polar	33892256
Homocitrulline,6TMS,isomer #1	C[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)C	2166.4	Standard polar	33892256
Homocitrulline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCNC(N)=O	2275.9	Semi standard non polar	33892256
Homocitrulline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCCCNC(N)=O)C(=O)O	2342.5	Semi standard non polar	33892256
Homocitrulline,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N)C(=O)O	2355.5	Semi standard non polar	33892256
Homocitrulline,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CCCC[C@H](N)C(=O)O)C(N)=O	2282.5	Semi standard non polar	33892256
Homocitrulline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCCCNC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C	2561.2	Semi standard non polar	33892256
Homocitrulline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCCCNC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C	2357.2	Standard non polar	33892256
Homocitrulline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCCCNC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C	3333.9	Standard polar	33892256
Homocitrulline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	2590.6	Semi standard non polar	33892256
Homocitrulline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	2340.1	Standard non polar	33892256
Homocitrulline,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	3182.3	Standard polar	33892256
Homocitrulline,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C	2451.7	Semi standard non polar	33892256
Homocitrulline,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C	2404.3	Standard non polar	33892256
Homocitrulline,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C	3508.6	Standard polar	33892256
Homocitrulline,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	2691.7	Semi standard non polar	33892256
Homocitrulline,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	2331.1	Standard non polar	33892256
Homocitrulline,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	3056.0	Standard polar	33892256
Homocitrulline,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N([C@@H](CCCCNC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C	2683.0	Semi standard non polar	33892256
Homocitrulline,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N([C@@H](CCCCNC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C	2411.3	Standard non polar	33892256
Homocitrulline,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N([C@@H](CCCCNC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C	3434.7	Standard polar	33892256
Homocitrulline,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O	2591.4	Semi standard non polar	33892256
Homocitrulline,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O	2437.2	Standard non polar	33892256
Homocitrulline,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N[C@@H](CCCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O	3248.0	Standard polar	33892256
Homocitrulline,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C(=O)NCCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	2619.6	Semi standard non polar	33892256
Homocitrulline,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C(=O)NCCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	2429.6	Standard non polar	33892256
Homocitrulline,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C(=O)NCCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	3332.5	Standard polar	33892256
Homocitrulline,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	2583.2	Semi standard non polar	33892256
Homocitrulline,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	2413.4	Standard non polar	33892256
Homocitrulline,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)NC(=O)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C	3302.1	Standard polar	33892256
Homocitrulline,3TBDMS,isomer #1	CC(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)C	2872.4	Semi standard non polar	33892256
Homocitrulline,3TBDMS,isomer #1	CC(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)C	2496.1	Standard non polar	33892256
Homocitrulline,3TBDMS,isomer #1	CC(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)C	2846.1	Standard polar	33892256
Homocitrulline,3TBDMS,isomer #10	CC(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)C	2818.2	Semi standard non polar	33892256
Homocitrulline,3TBDMS,isomer #10	CC(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)C	2708.2	Standard non polar	33892256
Homocitrulline,3TBDMS,isomer #10	CC(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)C	3083.7	Standard polar	33892256
Homocitrulline,3TBDMS,isomer #2	CC(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)C	2891.3	Semi standard non polar	33892256
Homocitrulline,3TBDMS,isomer #2	CC(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)C	2641.8	Standard non polar	33892256
Homocitrulline,3TBDMS,isomer #2	CC(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)C	3209.5	Standard polar	33892256
Homocitrulline,3TBDMS,isomer #3	CC(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)C	2726.1	Semi standard non polar	33892256
Homocitrulline,3TBDMS,isomer #3	CC(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)C	2595.1	Standard non polar	33892256
Homocitrulline,3TBDMS,isomer #3	CC(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)C	3125.6	Standard polar	33892256
Homocitrulline,3TBDMS,isomer #4	CC(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)C	2799.0	Semi standard non polar	33892256
Homocitrulline,3TBDMS,isomer #4	CC(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)C	2659.4	Standard non polar	33892256
Homocitrulline,3TBDMS,isomer #4	CC(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)C	3013.4	Standard polar	33892256
Homocitrulline,3TBDMS,isomer #5	CC(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)C	2734.9	Semi standard non polar	33892256
Homocitrulline,3TBDMS,isomer #5	CC(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)C	2615.7	Standard non polar	33892256
Homocitrulline,3TBDMS,isomer #5	CC(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)C	3032.4	Standard polar	33892256
Homocitrulline,3TBDMS,isomer #6	CC(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	2922.3	Semi standard non polar	33892256
Homocitrulline,3TBDMS,isomer #6	CC(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	2638.5	Standard non polar	33892256
Homocitrulline,3TBDMS,isomer #6	CC(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	2885.9	Standard polar	33892256
Homocitrulline,3TBDMS,isomer #7	CC(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	2869.4	Semi standard non polar	33892256
Homocitrulline,3TBDMS,isomer #7	CC(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	2611.9	Standard non polar	33892256
Homocitrulline,3TBDMS,isomer #7	CC(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	2901.9	Standard polar	33892256
Homocitrulline,3TBDMS,isomer #8	CC(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)C	2976.8	Semi standard non polar	33892256
Homocitrulline,3TBDMS,isomer #8	CC(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)C	2567.3	Standard non polar	33892256
Homocitrulline,3TBDMS,isomer #8	CC(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)C	2922.8	Standard polar	33892256
Homocitrulline,3TBDMS,isomer #9	CC(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)=O	2863.1	Semi standard non polar	33892256
Homocitrulline,3TBDMS,isomer #9	CC(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)=O	2658.3	Standard non polar	33892256
Homocitrulline,3TBDMS,isomer #9	CC(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)=O	3167.0	Standard polar	33892256
Homocitrulline,4TBDMS,isomer #1	CC(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)C	3054.9	Semi standard non polar	33892256
Homocitrulline,4TBDMS,isomer #1	CC(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)C	2806.6	Standard non polar	33892256
Homocitrulline,4TBDMS,isomer #1	CC(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)C	2779.4	Standard polar	33892256
Homocitrulline,4TBDMS,isomer #2	CC(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)C	3006.6	Semi standard non polar	33892256
Homocitrulline,4TBDMS,isomer #2	CC(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)C	2756.5	Standard non polar	33892256
Homocitrulline,4TBDMS,isomer #2	CC(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)C	2806.4	Standard polar	33892256
Homocitrulline,4TBDMS,isomer #3	CC(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)C	3169.6	Semi standard non polar	33892256
Homocitrulline,4TBDMS,isomer #3	CC(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)C	2743.7	Standard non polar	33892256
Homocitrulline,4TBDMS,isomer #3	CC(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)C	2847.4	Standard polar	33892256
Homocitrulline,4TBDMS,isomer #4	CC(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)C	3093.7	Semi standard non polar	33892256
Homocitrulline,4TBDMS,isomer #4	CC(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)C	2829.9	Standard non polar	33892256
Homocitrulline,4TBDMS,isomer #4	CC(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)C	3139.4	Standard polar	33892256
Homocitrulline,4TBDMS,isomer #5	CC(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)C	2998.8	Semi standard non polar	33892256
Homocitrulline,4TBDMS,isomer #5	CC(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)C	2895.4	Standard non polar	33892256
Homocitrulline,4TBDMS,isomer #5	CC(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)C	2932.1	Standard polar	33892256
Homocitrulline,4TBDMS,isomer #6	CC(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)C	3205.0	Semi standard non polar	33892256
Homocitrulline,4TBDMS,isomer #6	CC(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)C	2876.2	Standard non polar	33892256
Homocitrulline,4TBDMS,isomer #6	CC(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)C	2833.1	Standard polar	33892256
Homocitrulline,4TBDMS,isomer #7	CC(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	3101.6	Semi standard non polar	33892256
Homocitrulline,4TBDMS,isomer #7	CC(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	2893.9	Standard non polar	33892256
Homocitrulline,4TBDMS,isomer #7	CC(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	2815.1	Standard polar	33892256
Homocitrulline,4TBDMS,isomer #8	CC(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)C	3123.7	Semi standard non polar	33892256
Homocitrulline,4TBDMS,isomer #8	CC(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)C	2830.4	Standard non polar	33892256
Homocitrulline,4TBDMS,isomer #8	CC(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)C	2867.3	Standard polar	33892256
Homocitrulline,5TBDMS,isomer #1	CC(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)C	3404.1	Semi standard non polar	33892256
Homocitrulline,5TBDMS,isomer #1	CC(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)C	3041.5	Standard non polar	33892256
Homocitrulline,5TBDMS,isomer #1	CC(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)C	2765.8	Standard polar	33892256
Homocitrulline,5TBDMS,isomer #2	CC(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)C	3262.9	Semi standard non polar	33892256
Homocitrulline,5TBDMS,isomer #2	CC(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)C	3052.6	Standard non polar	33892256
Homocitrulline,5TBDMS,isomer #2	CC(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)C	2738.9	Standard polar	33892256
Homocitrulline,5TBDMS,isomer #3	CC(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)C	3366.7	Semi standard non polar	33892256
Homocitrulline,5TBDMS,isomer #3	CC(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)C	3002.0	Standard non polar	33892256
Homocitrulline,5TBDMS,isomer #3	CC(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)C	2804.0	Standard polar	33892256
Homocitrulline,5TBDMS,isomer #4	CC(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)C	3387.0	Semi standard non polar	33892256
Homocitrulline,5TBDMS,isomer #4	CC(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)C	3119.9	Standard non polar	33892256
Homocitrulline,5TBDMS,isomer #4	CC(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)C	2774.8	Standard polar	33892256
Homocitrulline,6TBDMS,isomer #1	CC(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)C	3604.8	Semi standard non polar	33892256
Homocitrulline,6TBDMS,isomer #1	CC(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)C	3297.7	Standard non polar	33892256
Homocitrulline,6TBDMS,isomer #1	CC(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)C	2784.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Homocitrulline GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00di-0900000000-74fcbf67e1025457671a	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Homocitrulline GC-EI-TOF (Non-derivatized)	splash10-00di-0900000000-74fcbf67e1025457671a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homocitrulline GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9100000000-560475aa29e1d94e59aa	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homocitrulline GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9700000000-ef60915445de08613bb1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homocitrulline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homocitrulline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homocitrulline GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homocitrulline GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homocitrulline GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homocitrulline GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homocitrulline GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homocitrulline GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homocitrulline GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00di-1900000000-adcca2902e0538d46b16	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-001i-9200000000-1fb814f74322670c53a2	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-053r-9000000000-0940c0b18cf743baf367	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline 30V, Positive-QTOF	splash10-001i-9100000000-cc77b5afd311cbae0fa8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline 40V, Positive-QTOF	splash10-053r-9000000000-a0189e6f8078c6ffa520	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline 20V, Negative-QTOF	splash10-0002-9300000000-ece511f06e8ad8996456	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline 40V, Negative-QTOF	splash10-054k-9000000000-6fc6f1f7981d8d290c04	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline 0V, Positive-QTOF	splash10-01ox-2930000000-fb8aea8c8cb6fa1f6980	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline 10V, Negative-QTOF	splash10-0005-4900000000-9d6c42dcd46ed350e0d6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline 40V, Negative-QTOF	splash10-0006-9000000000-28a7ec59b0224b2b1044	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline 10V, Positive-QTOF	splash10-0pir-8900000000-ebaf5608fe25e11a4a6f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline 30V, Positive-QTOF	splash10-0a4i-9000000000-766ff7efc90e65dc3cc4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline 20V, Negative-QTOF	splash10-0002-1900000000-4a46de28055906c905e4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline 30V, Negative-QTOF	splash10-0005-7900000000-cf282e5450dc67e5a74e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline 0V, Positive-QTOF	splash10-01ox-1950000000-5b126d209e94f7a29c4e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline 20V, Positive-QTOF	splash10-003r-9600000000-8bc13bf563ece5c33874	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline 10V, Positive-QTOF	splash10-00b9-1900000000-db388565404b40f99df5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline 40V, Positive-QTOF	splash10-0a59-9000000000-c3763a240b1b1a1329f5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Homocitrulline 10V, Positive-QTOF	splash10-00fr-1900000000-853bd3fba3289e99c342	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homocitrulline 10V, Positive-QTOF	splash10-006y-0900000000-8e7e33c59412f835b2c5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homocitrulline 20V, Positive-QTOF	splash10-0fam-4900000000-32c82cff8160c02dccef	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homocitrulline 40V, Positive-QTOF	splash10-001i-9000000000-ce7fde8e34720158c0b2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homocitrulline 10V, Negative-QTOF	splash10-002n-3900000000-9f2e58f8c995982ec6ad	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homocitrulline 20V, Negative-QTOF	splash10-002e-4900000000-5bdd3f534ea48aaaccb7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homocitrulline 40V, Negative-QTOF	splash10-0006-9000000000-04f0b7eb9d2e035a6fa2	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+H]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	5.0 (0.0-12.0) uM	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ...	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected and Quantified	<7.013 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	0 - 10.18 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 10.18 umol/mmol creatinine	Infant (1 - 6 months old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 10.18 umol/mmol creatinine	Infant (6 months - <1 year old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 10.18 umol/mmol creatinine	Children (1 - 2 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 10.18 umol/mmol creatinine	Children (2 - 4 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 10.18 umol/mmol creatinine	Children (4 - 13 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 10.18 umol/mmol creatinine	Adolescent (13 - 21 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 10.18 umol/mmol creatinine	Adult (>21 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	6.0 (0-8.8) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17053917	details
Urine	Detected and Quantified	<3.73 umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	<3.39 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	<33.36 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	1.24-17.87 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	7.5 (3.8-13.8) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	3.14 (2.45-4.68) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	<8.031 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	11.998 +/- 9.054 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	63-83 umol/mmol creatinine	Children (1-13 years old)	Both	Hyperlysinemia I, familial	23890588	details
Urine	Detected and Quantified	8.359 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
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 ] 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
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Hyperlysinemia I, familial
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

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)
238700 (Hyperlysinemia I, familial)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Homocitrulline

METLIN ID

PubChem Compound

65072

PDB ID

Not Available

ChEBI ID

17443

Food Biomarker Ontology

Not Available

VMH ID

HMCR

MarkerDB ID

MDB00029987

Good Scents ID

Not Available

References

Synthesis Reference

Stark, 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

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
Evered DF, Vadgama JV: Absorption of homocitrulline from the gastrointestinal tract. Br J Nutr. 1983 Jan;49(1):35-42. [PubMed:6821687 ]
Kato T, Sano M, Mizutani N, Hayakawa C: Homocitrullinuria and homoargininuria in hyperargininaemia. J Inherit Metab Dis. 1988;11(3):261-5. [PubMed:2466169 ]
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 ]
Kato T, Sano M, Mizutani N: Homocitrullinuria and homoargininuria in lysinuric protein intolerance. J Inherit Metab Dis. 1989;12(2):157-61. [PubMed:2474087 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Showing metabocard for Homocitrulline (HMDB0000679)

MOL for HMDB0000679 (Homocitrulline)

3D MOL for HMDB0000679 (Homocitrulline)

3D SDF for HMDB0000679 (Homocitrulline)

3D-SDF for HMDB0000679 (Homocitrulline)

PDB for HMDB0000679 (Homocitrulline)

3D PDB for HMDB0000679 (Homocitrulline)

SMILES for HMDB0000679 (Homocitrulline)

INCHI for HMDB0000679 (Homocitrulline)

Structure for HMDB0000679 (Homocitrulline)

3D Structure for HMDB0000679 (Homocitrulline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra