Bovine Metabolome Database: Showing metabocard for Homocitrulline (BMDB0000679)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:34:48 UTC

Update Date

2020-05-11 20:37:34 UTC

BMDB ID

BMDB0000679

Secondary Accession Numbers

BMDB00679

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. Based on a literature review a significant number of articles have been published on Homocitrulline.

Structure

MOL SDF PDB SMILES InChI

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

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00di-0900000000-74fcbf67e1025457671a	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0900000000-74fcbf67e1025457671a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9100000000-560475aa29e1d94e59aa	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9700000000-ef60915445de08613bb1	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-1900000000-adcca2902e0538d46b16	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9200000000-1fb814f74322670c53a2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-053r-9000000000-0940c0b18cf743baf367	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-9100000000-cc77b5afd311cbae0fa8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-053r-9000000000-a0189e6f8078c6ffa520	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9300000000-ece511f06e8ad8996456	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-054k-9000000000-6fc6f1f7981d8d290c04	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-01ox-2930000000-fb8aea8c8cb6fa1f6980	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0005-4900000000-9d6c42dcd46ed350e0d6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-28a7ec59b0224b2b1044	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0pir-8900000000-ebaf5608fe25e11a4a6f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-9000000000-766ff7efc90e65dc3cc4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1900000000-4a46de28055906c905e4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0005-7900000000-cf282e5450dc67e5a74e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-01ox-1950000000-5b126d209e94f7a29c4e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-003r-9600000000-8bc13bf563ece5c33874	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00b9-1900000000-db388565404b40f99df5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9000000000-c3763a240b1b1a1329f5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00fr-1900000000-853bd3fba3289e99c342	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006y-0900000000-8e7e33c59412f835b2c5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fam-4900000000-32c82cff8160c02dccef	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-ce7fde8e34720158c0b2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002n-3900000000-9f2e58f8c995982ec6ad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002e-4900000000-5bdd3f534ea48aaaccb7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-04f0b7eb9d2e035a6fa2	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Liver
Placenta

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000679

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

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)

Not Available

General References

Not Available

Showing metabocard for Homocitrulline (BMDB0000679)

Structure for BMDB0000679 (Homocitrulline)