NP-MRD: Showing NP-Card for 4-Hydroxyarginine (NP0077476)

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Record Information

Version

2.0

Created at

2022-04-28 22:37:19 UTC

Updated at

2022-04-28 22:37:20 UTC

NP-MRD ID

NP0077476

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Hydroxyarginine

Description

(4R)-4-hydroxy-L-arginine 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. 4-Hydroxyarginine is found in Anthrophopleura japonica, Lens culinaris and Polycheira ruescens. Based on a literature review very few articles have been published on (4R)-4-hydroxy-L-arginine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200372D          

 13 12  0  0  1  0            999 V2000
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    3.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  1  0  0  0
  3 12  1  1  0  0  0
  1 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077476

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](C[C@@H](O)CNC(N)=N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H14N4O3/c7-4(5(12)13)1-3(11)2-10-6(8)9/h3-4,11H,1-2,7H2,(H,12,13)(H4,8,9,10)/t3-,4+/m1/s1

> <INCHI_KEY>
OPCBKDJCJYBGTQ-DMTCNVIQSA-N

> <FORMULA>
C6H14N4O3

> <MOLECULAR_WEIGHT>
190.203

> <EXACT_MASS>
190.106590327

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.45943466289563

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4R)-2-amino-5-carbamimidamido-4-hydroxypentanoic acid

> <ALOGPS_LOGP>
-3.96

> <JCHEM_LOGP>
-4.312020812610223

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.838256297728822

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1976627287882224

> <JCHEM_PKA_STRONGEST_BASIC>
11.81028295626412

> <JCHEM_POLAR_SURFACE_AREA>
145.45

> <JCHEM_REFRACTIVITY>
55.24099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-hydroxy-L-arginine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.596   4.771   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      13.598   4.771   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      16.266   4.771   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      14.932   2.461   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      10.931   6.311   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       8.264   6.311   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       6.930   2.461   0.000  0.00  0.00           O+0
CONECT    1    2    3   13                                                  
CONECT    2    1                                                            
CONECT    3    1    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5                                                            
CONECT   12    3                                                            
CONECT   13    1                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Value	Source
(2S,4R)-2-Amino-5-{[amino(imino)methyl]amino}-4-hydroxypentanoic acid	ChEBI
(2S,4R)-2-Amino-5-{[amino(imino)methyl]amino}-4-hydroxypentanoate	Generator

Chemical Formula

C₆H₁₄N₄O₃

Average Mass

190.2030 Da

Monoisotopic Mass

190.10659 Da

IUPAC Name

(2S,4R)-2-amino-5-carbamimidamido-4-hydroxypentanoic acid

Traditional Name

(4R)-4-hydroxy-L-arginine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H14N4O3/c7-4(5(12)13)1-3(11)2-10-6(8)9/h3-4,11H,1-2,7H2,(H,12,13)(H4,8,9,10)/t3-,4+/m1/s1

InChI Key

OPCBKDJCJYBGTQ-DMTCNVIQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anthrophopleura japonica	-	KNApSAcK
Lens culinaris	Plant	KNApSAcK
Polycheira ruescens	Animalia	KNApSAcK

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
Short-chain hydroxy acid
Fatty acid
1,3-aminoalcohol
Guanidine
Secondary alcohol
Amino acid
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Amine
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

gamma-hydroxy-L-arginine (CHEBI:47816 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	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	-4	ALOGPS
logP	-4.3	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	2.2	ChemAxon
pKa (Strongest Basic)	11.81	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	145.45 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	55.24 m³·mol⁻¹	ChemAxon
Polarizability	18.46 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21865456

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17756747

PDB ID

Not Available

ChEBI ID

47816

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-Hydroxyarginine (NP0077476)

MOL for NP0077476 (4-Hydroxyarginine)

3D MOL for NP0077476 (4-Hydroxyarginine)

3D SDF for NP0077476 (4-Hydroxyarginine)

3D-SDF for NP0077476 (4-Hydroxyarginine)

PDB for NP0077476 (4-Hydroxyarginine)

3D PDB for NP0077476 (4-Hydroxyarginine)

SMILES for NP0077476 (4-Hydroxyarginine)

INCHI for NP0077476 (4-Hydroxyarginine)

Structure for NP0077476 (4-Hydroxyarginine)

3D Structure for NP0077476 (4-Hydroxyarginine)