NP-MRD: Showing NP-Card for Homo-L-arginine (NP0001088)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-19 23:58:45 UTC

NP-MRD ID

NP0001088

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Homo-L-arginine

Description

Homo-L-arginine, also known as N6-(aminoiminomethyl)-L-lysine or N6-amidino-L-lysine, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. More specifically, Homo-L-arginine is a naturally occurring, non-proteinogenic, cationic amino acid. It is formed in the liver in a reaction catalyzed by L-arginine:Glycine amidinotransferase (AGAT) when transferring the amidino group from arginine to lysine. It is an alternative substrate for nitric oxide (NO) synthase. Homo-L-arginine increases the availability of NO and thereby affects endothelial function. High homoarginine levels may exert positive actions that are relevant to cardiovascular health, including enhanced endothelial function, inhibition of platelet aggregation and stimulation of insulin secretion (PMID: 30866658 ). Recent studies have demonstrated that low serum homoarginine levels are a strong predictor of cardiovascular mortality (PMID: 24583919 ). Homo-L-arginine is a substrate of the human cationic amino acid CAT1 [solute carrier family 7 (SLC7A1)], CAT2A (SLC7A2A) or CAT2B (SLC7A2B) (PMID: 28684763 ). According to published human metabolomic data, Homo-L-arginine can be found primarily in blood, cerebrospinal fluid (CSF), and urine, as well as in human intestinal and testes tissues. Moreover, Homo-L-arginine has been found to be associated with liver cirrhosis and the genetic disorder, hyperargininemia. Homoarginine is an organ-specific uncompetitive inhibitor of human liver and bone alkaline phosphohydrolase (PMID: 5063678 ).

Structure

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

HMDB0000670
     RDKit          3D
Homo-L-arginine
 29 28  0  0  0  0  0  0  0  0999 V2000
   -4.3069    1.4322   -1.1089 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1408    0.4090   -0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1548   -0.5864   -0.3265 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9711    0.3000    0.4622 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6998    0.2068   -0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5421    0.0960    0.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234    0.0054   -0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500   -0.1096    0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1465   -0.1922   -0.1274 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9647   -1.3503   -0.9505 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4135   -0.2064    0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2465   -1.1449    0.5432 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6785    0.8827    1.4534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5759    2.1913   -1.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0358   -0.3789    0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0561   -1.4969   -0.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0816    0.2926    1.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6063    1.1150   -0.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544   -0.6599   -0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5551    0.8593    1.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6808   -0.8919    1.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6545   -0.8168   -0.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317    0.9481   -0.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9385   -0.9799    1.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1146    0.8146    1.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1390    0.7370   -0.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3793   -1.1760   -1.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5452   -2.1340   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4355    1.8342    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  6
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END

HMDB0000670
     RDKit          3D
Homo-L-arginine
 29 28  0  0  0  0  0  0  0  0999 V2000
   -4.3069    1.4322   -1.1089 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1408    0.4090   -0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1548   -0.5864   -0.3265 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9711    0.3000    0.4622 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6998    0.2068   -0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5421    0.0960    0.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234    0.0054   -0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500   -0.1096    0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1465   -0.1922   -0.1274 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9647   -1.3503   -0.9505 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4135   -0.2064    0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2465   -1.1449    0.5432 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6785    0.8827    1.4534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5759    2.1913   -1.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0358   -0.3789    0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0561   -1.4969   -0.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0816    0.2926    1.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6063    1.1150   -0.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544   -0.6599   -0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5551    0.8593    1.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6808   -0.8919    1.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6545   -0.8168   -0.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317    0.9481   -0.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9385   -0.9799    1.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1146    0.8146    1.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1390    0.7370   -0.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3793   -1.1760   -1.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5452   -2.1340   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4355    1.8342    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  6
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0    8685.0178682.603   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8686.3538683.373   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    8686.3538684.912   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    8678.3458684.912   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0    8677.0118682.603   0.000  0.00  0.00           N+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    HMDB0000670
HETATM    1  N1  UNL     1      -4.307   1.432  -1.109  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.141   0.409  -0.340  1.00  0.00           C  
HETATM    3  N2  UNL     1      -5.155  -0.586  -0.326  1.00  0.00           N  
HETATM    4  N3  UNL     1      -2.971   0.300   0.462  1.00  0.00           N  
HETATM    5  C2  UNL     1      -1.700   0.207  -0.229  1.00  0.00           C  
HETATM    6  C3  UNL     1      -0.542   0.096   0.739  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.723   0.005  -0.048  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.950  -0.110   0.828  1.00  0.00           C  
HETATM    9  C6  UNL     1       3.147  -0.192  -0.127  1.00  0.00           C  
HETATM   10  N4  UNL     1       2.965  -1.350  -0.951  1.00  0.00           N  
HETATM   11  C7  UNL     1       4.414  -0.206   0.623  1.00  0.00           C  
HETATM   12  O1  UNL     1       5.247  -1.145   0.543  1.00  0.00           O  
HETATM   13  O2  UNL     1       4.679   0.883   1.453  1.00  0.00           O  
HETATM   14  H1  UNL     1      -3.576   2.191  -1.146  1.00  0.00           H  
HETATM   15  H2  UNL     1      -6.036  -0.379   0.199  1.00  0.00           H  
HETATM   16  H3  UNL     1      -5.056  -1.497  -0.811  1.00  0.00           H  
HETATM   17  H4  UNL     1      -3.082   0.293   1.484  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.606   1.115  -0.859  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.754  -0.660  -0.903  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.555   0.859   1.513  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.681  -0.892   1.267  1.00  0.00           H  
HETATM   22  H9  UNL     1       0.655  -0.817  -0.768  1.00  0.00           H  
HETATM   23  H10 UNL     1       0.832   0.948  -0.637  1.00  0.00           H  
HETATM   24  H11 UNL     1       1.939  -0.980   1.485  1.00  0.00           H  
HETATM   25  H12 UNL     1       2.115   0.815   1.418  1.00  0.00           H  
HETATM   26  H13 UNL     1       3.139   0.737  -0.759  1.00  0.00           H  
HETATM   27  H14 UNL     1       2.379  -1.176  -1.797  1.00  0.00           H  
HETATM   28  H15 UNL     1       2.545  -2.134  -0.415  1.00  0.00           H  
HETATM   29  H16 UNL     1       4.435   1.834   1.190  1.00  0.00           H  
CONECT    1    2    2   14
CONECT    2    3    4
CONECT    3   15   16
CONECT    4    5   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8   22   23
CONECT    8    9   24   25
CONECT    9   10   11   26
CONECT   10   27   28
CONECT   11   12   12   13
CONECT   13   29
END

HMDB0000670
     RDKit          3D
Homo-L-arginine
 29 28  0  0  0  0  0  0  0  0999 V2000
   -4.3069    1.4322   -1.1089 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1408    0.4090   -0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1548   -0.5864   -0.3265 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9711    0.3000    0.4622 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6998    0.2068   -0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5421    0.0960    0.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234    0.0054   -0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500   -0.1096    0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1465   -0.1922   -0.1274 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9647   -1.3503   -0.9505 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4135   -0.2064    0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2465   -1.1449    0.5432 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6785    0.8827    1.4534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5759    2.1913   -1.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0358   -0.3789    0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0561   -1.4969   -0.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0816    0.2926    1.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6063    1.1150   -0.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544   -0.6599   -0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5551    0.8593    1.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6808   -0.8919    1.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6545   -0.8168   -0.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317    0.9481   -0.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9385   -0.9799    1.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1146    0.8146    1.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1390    0.7370   -0.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3793   -1.1760   -1.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5452   -2.1340   -0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4355    1.8342    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  6
 10 27  1  0
 10 28  1  0
 13 29  1  0
M  END

View in JSmol

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 Mass

188.2275 Da

Monoisotopic Mass

188.12733 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Annona squamosa	KNApSAcK Database	22123792
Lathyrus cicera	KNApSAcK Database	22123792
Lathyrus sativus	KNApSAcK Database	22123792
Lathyrus tingitanus	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633

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	363900 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.58 g/L	ALOGPS
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

Good Scents ID

rw1346121

References

General References

Mizutani N, Hayakawa C, Ohya Y, Watanabe K, Watanabe Y, Mori A: Guanidino compounds in hyperargininemia. Tohoku J Exp Med. 1987 Nov;153(3):197-205. [PubMed:3433275 ]
Mori A, Watanabe Y, Fujimoto N: Fluorometrical analysis of guanidino compounds in human cerebrospinal fluid. J Neurochem. 1982 Feb;38(2):448-50. [PubMed:7108550 ]
Tamura Y, Fujii S: Purification of human plasma kallikrein and urokinase by affinity chromatography. J Biochem. 1976 Sep;80(3):507-11. [PubMed:824284 ]
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 ]
Marescau B, Qureshi IA, De Deyn P, Letarte J, Ryba R, Lowenthal A: Guanidino compounds in plasma, urine and cerebrospinal fluid of hyperargininemic patients during therapy. Clin Chim Acta. 1985 Feb 28;146(1):21-7. [PubMed:3987036 ]
Brock DJ: Amniotic fluid alkaline phosphatase isoenzymes in early prenatal diagnosis of cystic fibrosis. Lancet. 1983 Oct 22;2(8356):941-3. [PubMed:6138505 ]
Crofton PM, Smith AF: Alkaline phosphatase of high and low molecular mass in human serum and bile: a comparative study of kinetic properties. Clin Chem. 1980 Mar;26(3):451-6. [PubMed:7363466 ]
el-Mokhefi Z, Duvivier J, Plomteux G, Gielen J: [Biochemical characterization of a high-molecular weight alkaline phosphatase in a patient with cholangiocarcinoma (alpha-1 alkaline phosphatase)]. Ann Biol Clin (Paris). 1985;43(3):215-20. [PubMed:2411171 ]
Muller F, Berg S, Frot JC, Boue J, Boue A: Prenatal diagnosis of cystic fibrosis. I. Prospective study of 51 pregnancies. Prenat Diagn. 1985 Mar-Apr;5(2):97-108. [PubMed:2581242 ]
Chang CH, Angellis D, Fishman WH: Presence of the rare D-variant heat-stable, placental-type alkaline phosphatase in normal human testis. Cancer Res. 1980 May;40(5):1506-10. [PubMed:6154531 ]
Gatti R, Gioia MG: Anisoin: a useful pre-chromatographic derivatization fluorogenic reagent for LC analysis of guanidino compounds. J Pharm Biomed Anal. 2006 Sep 11;42(1):11-6. Epub 2006 Feb 3. [PubMed:16460903 ]
Marescau B, De Deyn PP, Lowenthal A, Qureshi IA, Antonozzi I, Bachmann C, Cederbaum SD, Cerone R, Chamoles N, Colombo JP, et al.: Guanidino compound analysis as a complementary diagnostic parameter for hyperargininemia: follow-up of guanidino compound levels during therapy. Pediatr Res. 1990 Mar;27(3):297-303. [PubMed:1690873 ]
Suzuki K, Yoshimura Y, Hisada Y, Matsumoto A: Sensitivity of intestinal alkaline phosphatase to L-homoarginine and its regulation by subunit-subunit interaction. Jpn J Pharmacol. 1994 Feb;64(2):97-102. [PubMed:7518015 ]
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 ]

Showing NP-Card for Homo-L-arginine (NP0001088)

MOL for NP0001088 (Homo-L-arginine)

3D MOL for NP0001088 (Homo-L-arginine)

3D SDF for NP0001088 (Homo-L-arginine)

3D-SDF for NP0001088 (Homo-L-arginine)

PDB for NP0001088 (Homo-L-arginine)

3D PDB for NP0001088 (Homo-L-arginine)

SMILES for NP0001088 (Homo-L-arginine)

INCHI for NP0001088 (Homo-L-arginine)

Structure for NP0001088 (Homo-L-arginine)

3D Structure for NP0001088 (Homo-L-arginine)