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

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:45 UTC
NP-MRD IDNP0001088
Secondary Accession NumbersNone
Natural Product Identification
Common NameHomo-L-arginine
DescriptionHomo-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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001088 (Homo-L-arginine)


  Mrv1652304202019212D          

 13 12  0  0  0  0            999 V2000
10009.830310008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.546010008.9496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10011.259510008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.975010008.9496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10011.259510007.7121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.546010009.7744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10009.114810008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.400710008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.686010008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.970910008.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10006.256210008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.256210009.7744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10005.541510008.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  6  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
Download

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

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
Download

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


  Mrv1652304202019212D          

 13 12  0  0  0  0            999 V2000
10009.830310008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.546010008.9496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10011.259510008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.975010008.9496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10011.259510007.7121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.546010009.7744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10009.114810008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.400710008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.686010008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.970910008.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10006.256210008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.256210009.7744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10005.541510008.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  6  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001088

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C7H16N4O2

> <MOLECULAR_WEIGHT>
188.2275

> <EXACT_MASS>
188.127325776

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.03779635520079

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-6-carbamimidamidohexanoic acid

> <ALOGPS_LOGP>
-3.73

> <JCHEM_LOGP>
-2.722308785706772

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4910361487073844

> <JCHEM_PKA_STRONGEST_BASIC>
12.302434226350789

> <JCHEM_POLAR_SURFACE_AREA>
125.22

> <JCHEM_REFRACTIVITY>
58.5241

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-homoarginine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

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

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
Download

PDB for NP0001088 (Homo-L-arginine)

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

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
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SMILES for NP0001088 (Homo-L-arginine)

N[C@@H](CCCCNC(N)=N)C(O)=O
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INCHI for NP0001088 (Homo-L-arginine)

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
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Synonyms
ValueSource
HomoarginineChEBI
L-N(6)-AmidinolysineChEBI
N6-(Aminoiminomethyl)-L-lysineChEBI
N6-Amidino-L-lysineChEBI
N6-Amidino-lysineChEBI
L-HomoarginineKegg
Homo-L-arginineChEBI
Chemical FormulaC7H16N4O2
Average Mass188.2275 Da
Monoisotopic Mass188.12733 Da
IUPAC Name(2S)-2-amino-6-carbamimidamidohexanoic acid
Traditional NameL-homoarginine
CAS Registry Number156-86-5
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 KeyQUOGESRFPZDMMT-YFKPBYRVSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Annona squamosaKNApSAcK Database
Lathyrus ciceraKNApSAcK Database
Lathyrus sativusKNApSAcK Database
Lathyrus tingitanusLOTUS Database
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point213 - 215 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility363900 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.58 g/LALOGPS
logP-3.7ALOGPS
logP-2.7ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.49ChemAxon
pKa (Strongest Basic)12.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area125.22 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity58.52 m³·mol⁻¹ChemAxon
Polarizability20.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000670
DrugBank IDDB03974
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112164
KNApSAcK IDC00001364
Chemspider ID8732
KEGG Compound IDC01924
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5640
PubChem Compound9085
PDB IDNot Available
ChEBI ID27747
Good Scents IDrw1346121
References
General References
  1. 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 ]
  2. 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 ]
  3. Tamura Y, Fujii S: Purification of human plasma kallikrein and urokinase by affinity chromatography. J Biochem. 1976 Sep;80(3):507-11. [PubMed:824284 ]
  4. 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 ]
  5. 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 ]
  6. Brock DJ: Amniotic fluid alkaline phosphatase isoenzymes in early prenatal diagnosis of cystic fibrosis. Lancet. 1983 Oct 22;2(8356):941-3. [PubMed:6138505 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]