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Showing NP-Card for hydroxyisoleucine (NP0195712)

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Record Information
Version2.0
Created at2022-09-04 13:37:40 UTC
Updated at2022-09-04 13:37:40 UTC
NP-MRD IDNP0195712
Secondary Accession NumbersNone
Natural Product Identification
Common Namehydroxyisoleucine
Description(4S)-4-hydroxy-L-isoleucine zwitterion, also known as (2S,3R,4S)-4-hydroxyisoleucine or 2-ammonio-2,3,5-trideoxy-3-methyl-L-ribonate, belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom (4S)-4-hydroxy-L-isoleucine zwitterion is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. hydroxyisoleucine is found in Trigonella foenum-graecum. hydroxyisoleucine was first documented in 2009 (PMID: 19850012). Based on a literature review very few articles have been published on (4S)-4-hydroxy-L-isoleucine zwitterion.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0195712 (hydroxyisoleucine)


  Mrv1652309042215372D          

 10  9  0  0  1  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
Download

3D MOL for NP0195712 (hydroxyisoleucine)

     RDKit          3D

 23 22  0  0  0  0  0  0  0  0999 V2000
   -2.4487    0.0444    0.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9500   -0.0206    0.7349 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6586    0.9108    1.7051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2736    0.1908   -0.5665 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7380   -0.9275   -1.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2219    0.1291   -0.5336 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6926   -1.1500   -0.0714 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8707    1.2278    0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6533    2.4471   -0.0274 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8110    0.9232    1.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8412   -0.9353    0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6355    0.7903   -0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0043    0.3803    1.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645   -1.0595    1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704    1.1283    2.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5815    1.1449   -0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9575   -1.8393   -0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6107   -0.6294   -2.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0804   -1.2464   -2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5519    0.2008   -1.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7376   -1.1686   -0.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5212   -1.3117    0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7938    0.7707    0.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8 10  1  0
  8  9  2  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  1
  3 15  1  0
  4 16  1  6
  5 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  6
  7 21  1  0
  7 22  1  0
 10 23  1  0
M  END
Download

3D SDF for NP0195712 (hydroxyisoleucine)


  Mrv1652309042215372D          

 10  9  0  0  1  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195712

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H13NO3/c1-3(4(2)8)5(7)6(9)10/h3-5,8H,7H2,1-2H3,(H,9,10)/t3-,4-,5-/m0/s1

> <INCHI_KEY>
OSCCDBFHNMXNME-YUPRTTJUSA-N

> <FORMULA>
C6H13NO3

> <MOLECULAR_WEIGHT>
147.174

> <EXACT_MASS>
147.089543283

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
14.685716310946045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S)-2-amino-4-hydroxy-3-methylpentanoic acid

> <JCHEM_LOGP>
-2.931421757828279

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.238137537934477

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.460320130533524

> <JCHEM_PKA_STRONGEST_BASIC>
9.215206644727141

> <JCHEM_POLAR_SURFACE_AREA>
83.55

> <JCHEM_REFRACTIVITY>
35.7416

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S)-2-amino-4-hydroxy-3-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0195712 (hydroxyisoleucine)

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PDB for NP0195712 (hydroxyisoleucine)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310  -0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.644   3.644   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for NP0195712 (hydroxyisoleucine)
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SMILES for NP0195712 (hydroxyisoleucine)
C[C@H](O)[C@H](C)[C@H](N)C(O)=O
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INCHI for NP0195712 (hydroxyisoleucine)
InChI=1S/C6H13NO3/c1-3(4(2)8)5(7)6(9)10/h3-5,8H,7H2,1-2H3,(H,9,10)/t3-,4-,5-/m0/s1
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View in JSmol
Synonyms
ValueSource
(2S,3R,4S)-4-HydroxyisoleucineChEBI
(4S)-4-Hydroxy-L-isoleucineChEBI
2-Ammonio-2,3,5-trideoxy-3-methyl-L-ribonateChEBI
2-Ammonio-2,3,5-trideoxy-3-methyl-L-ribonic acidGenerator
HydroxyisoleucineMeSH
(2S,3S,4R)-gamma-HydroxyisoleucineMeSH
Chemical FormulaC6H13NO3
Average Mass147.1740 Da
Monoisotopic Mass147.08954 Da
IUPAC Name(2S,3R,4S)-2-amino-4-hydroxy-3-methylpentanoic acid
Traditional Name(2S,3R,4S)-2-amino-4-hydroxy-3-methylpentanoic acid
CAS Registry NumberNot Available
SMILES
C[C@H](O)[C@H](C)[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C6H13NO3/c1-3(4(2)8)5(7)6(9)10/h3-5,8H,7H2,1-2H3,(H,9,10)/t3-,4-,5-/m0/s1
InChI KeyOSCCDBFHNMXNME-YUPRTTJUSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Trigonella foenum-graecumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentIsoleucine and derivatives  
Alternative Parents
Substituents
  • Isoleucine or derivatives
    • 

  • Alpha-amino acid
    • 

  • L-alpha-amino acid
    • 

  • Branched fatty acid
    • 

  • Hydroxy fatty acid
    • 

  • Methyl-branched fatty acid
    • 

  • Short-chain hydroxy acid
    • 

  • Fatty acyl
    • 

  • Fatty acid
    • 

  • 1,3-aminoalcohol
    • 

  • Amino acid
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Primary amine
    • 

  • Primary aliphatic amine
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organopnictogen compound
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.9ChemAxon
pKa (Strongest Acidic)2.46ChemAxon
pKa (Strongest Basic)9.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.74 m³·mol⁻¹ChemAxon
Polarizability14.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00054455  
Chemspider ID5293923  
KEGG Compound IDNot Available
BioCyc IDCPD-14635  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6918732  
PDB IDNot Available
ChEBI ID78247  
Good Scents IDNot Available
References
General References
  1. Kodera T, Smirnov SV, Samsonova NN, Kozlov YI, Koyama R, Hibi M, Ogawa J, Yokozeki K, Shimizu S: A novel l-isoleucine hydroxylating enzyme, l-isoleucine dioxygenase from Bacillus thuringiensis, produces (2S,3R,4S)-4-hydroxyisoleucine. Biochem Biophys Res Commun. 2009 Dec 18;390(3):506-10. doi: 10.1016/j.bbrc.2009.09.126. Epub 2009 Oct 20. [PubMed:19850012  ] 
  2. LOTUS database [Link]