Milk Composition Database: Showing metabocard for Homo-L-arginine (BMDB0000670)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:34:39 UTC

Update Date

2021-01-12 22:02:00 UTC

MCDB ID

BMDB0000670

Secondary Accession Numbers

BMDB00670

Metabolite Identification

Common Name

Homo-L-arginine

Description

Homo-L-arginine, also known as n6-amidino-lysine, 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. Homo-L-arginine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Homo-L-arginine exists in all living organisms, ranging from bacteria to humans. Homo-L-arginine is a potentially toxic compound. Homo-L-arginine has been found to be associated with the diseases known as cirrhosis; also homo-l-arginine has been linked to the inborn metabolic disorders including hyperargininemia.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Homoarginine	ChEBI
L-N(6)-Amidinolysine	ChEBI
N6-(Aminoiminomethyl)-L-lysine	ChEBI
N6-Amidino-L-lysine	ChEBI
N6-Amidino-lysine	ChEBI
L-Homoarginine	Kegg
Homo-L-arginine	ChEBI

Chemical Formula

C₇H₁₆N₄O₂

Average Molecular Weight

188.2275

Monoisotopic Molecular Weight

188.127325776

IUPAC Name

(2S)-2-amino-6-carbamimidamidohexanoic acid

Traditional Name

L-homoarginine

CAS Registry Number

156-86-5

SMILES

N[C@@H](CCCCNC(N)=N)C(O)=O

InChI Identifier

InChI=1S/C7H16N4O2/c8-5(6(12)13)3-1-2-4-11-7(9)10/h5H,1-4,8H2,(H,12,13)(H4,9,10,11)/t5-/m0/s1

InChI Key

QUOGESRFPZDMMT-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 acid
Fatty acyl
Guanidine
Amino acid
Carboximidamide
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Imine
Carbonyl group
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:27747 )
L-lysine derivative (CHEBI:27747 )
homoarginine (CHEBI:27747 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	213 - 215 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3.7	ALOGPS
logP	-2.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.49	ChemAxon
pKa (Strongest Basic)	12.3	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	125.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	58.52 m³·mol⁻¹	ChemAxon
Polarizability	20.04 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9200000000-4b838fa08e1357002dbf	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006x-8900000000-fed7c106a20ecedc84ae	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-1900000000-be624ee9b24e82eb0742	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9100000000-f4d4f5ac890116d181f0	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-053r-9000000000-4414ba2f5a6f7d2b30cc	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0900000000-46385e830fe015de53ab	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-0900000000-c6d6b6435e521a93b453	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0002-0900000000-6e5c16a8db2bbd58844f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-6900000000-a844ac9257f1ef5a3b23	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-f496e2b96544aa9df21d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-000i-0900000000-860f0c1c052c981b2f3b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-001c-1900000000-6ea950560557eb3afd98	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-9300000000-d110eb7150669bcdc29c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-9000000000-2f0ed2e02fdc77532125	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-001i-9000000000-d1b2d06e85c976b4efa5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-46385e830fe015de53ab	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-c6d6b6435e521a93b453	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-e278e373c633748b7f2a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-6900000000-2a53a55ea05925b3a0e7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-f496e2b96544aa9df21d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0900000000-860f0c1c052c981b2f3b	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000f-1900000000-78f1894c2529837e5d1a	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01qc-7900000000-c7e53e1427434aef74af	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-1920df59a18f799043ab	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000j-1900000000-c97e2b766559765479dd	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052b-5900000000-16bff7159fd55d679369	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-abe2fe3203bf8dcb8f8f	2017-07-26	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 28306241	details

External Links

HMDB ID

HMDB0000670

DrugBank ID

DB03974

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5640

PubChem Compound

9085

PDB ID

Not Available

ChEBI ID

27747

References

Synthesis Reference

Izumiya, Nobuo. Synthesis of DL-homoarginine and Na-methyl-DL-homoarginine. Nippon Kagaku Zasshi (1951), 72 521-3. CODEN: NPKZAZ ISSN:0369-5387. CAN 46:42183 AN 1952:42183

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
Karetnikova ES, Jarzebska N, Markov AG, Weiss N, Lentz SR, Rodionov RN: Is Homoarginine a Protective Cardiovascular Risk Factor? Arterioscler Thromb Vasc Biol. 2019 May;39(5):869-875. doi: 10.1161/ATVBAHA.118.312218. [PubMed:30866658 ]
Sobczak A, Prokopowicz A, Radek M, Szula M, Zaciera M, Kurek J, Goniewicz ML: Tobacco smoking decreases plasma concentration of the emerging cardiovascular risk marker, L-homoarginine. Circ J. 2014;78(5):1254-8. doi: 10.1253/circj.cj-13-1334. Epub 2014 Feb 28. [PubMed:24583919 ]
Chafai A, Fromm MF, Konig J, Maas R: The prognostic biomarker L-homoarginine is a substrate of the cationic amino acid transporters CAT1, CAT2A and CAT2B. Sci Rep. 2017 Jul 6;7(1):4767. doi: 10.1038/s41598-017-04965-2. [PubMed:28684763 ]
Lin CW, Fishman WH: L-Homoarginine. An organ-specific, uncompetitive inhibitor of human liver and bone alkaline phosphohydrolases. J Biol Chem. 1972 May 25;247(10):3082-7. [PubMed:5063678 ]

Showing metabocard for Homo-L-arginine (BMDB0000670)

Structure for BMDB0000670 (Homo-L-arginine)