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Showing NP-Card for hmva (NP0247921)

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Record Information
Version1.0
Created at2022-09-07 09:56:48 UTC
Updated at2022-09-07 09:56:49 UTC
NP-MRD IDNP0247921
Secondary Accession NumbersNone
Natural Product Identification
Common Namehmva
Description(2R,3S)-2-hydroxy-3-methylpentanoic acid, also known as (2R,3S)-hmva or (2R,3S)-isoleucic acid, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. hmva is found in Nicotiana tabacum. It was first documented in 1992 (PMID: 1429566). Based on a literature review very few articles have been published on (2R,3S)-2-hydroxy-3-methylpentanoic acid.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0247921 (hmva)


  Mrv1652309072211562D          

  9  8  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  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  1  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   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  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
Download

3D MOL for NP0247921 (hmva)

     RDKit          3D

 21 20  0  0  0  0  0  0  0  0999 V2000
   -1.7152   -1.4541    0.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5176   -0.1235    0.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453    0.4467    0.2804 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1713    1.8048   -0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9065   -0.4066   -0.3938 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5803   -0.4823   -1.7526 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2344    0.1702   -0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9367    0.5289   -1.1803 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7487    0.3334    1.0666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9210   -2.1771    0.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6888   -1.8676    0.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8494   -1.3383    1.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8448   -0.1912   -0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2258    0.5926    0.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0738    0.5829    1.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0885    1.6555   -1.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268    2.4659   -0.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1456    2.2644   -0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8843   -1.4051    0.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1733   -1.1089   -1.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4951   -0.2903    1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  9  1  0
  7  8  2  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  1
  4 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  1
  6 20  1  0
  9 21  1  0
M  END
Download

3D SDF for NP0247921 (hmva)


  Mrv1652309072211562D          

  9  8  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  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  1  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   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  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247921

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O3/c1-3-4(2)5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t4-,5+/m0/s1

> <INCHI_KEY>
RILPIWOPNGRASR-CRCLSJGQSA-N

> <FORMULA>
C6H12O3

> <MOLECULAR_WEIGHT>
132.159

> <EXACT_MASS>
132.078644246

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
13.70913401587886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
0.8602343683333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.044948135264622

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.25405925572059

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8957913795351873

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
32.4364

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
HMVA

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0247921 (hmva)

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PDB for NP0247921 (hmva)
HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-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  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310  -0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.644   3.644   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0247921 (hmva)
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SMILES for NP0247921 (hmva)
CC[C@H](C)[C@@H](O)C(O)=O
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INCHI for NP0247921 (hmva)
InChI=1S/C6H12O3/c1-3-4(2)5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t4-,5+/m0/s1
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View in JSmol
Synonyms
ValueSource
(2R,3S)-2-Hydroxy-3-methylvaleric acidChEBI
(2R,3S)-HMVAChEBI
(2R,3S)-Isoleucic acidChEBI
(R,S)-Isoleucic acidChEBI
HMVAChEBI
(2R,3S)-2-Hydroxy-3-methylvalerateGenerator
(2R,3S)-IsoleucateGenerator
(R,S)-IsoleucateGenerator
(2R,3S)-2-Hydroxy-3-methylpentanoateGenerator
Chemical FormulaC6H12O3
Average Mass132.1590 Da
Monoisotopic Mass132.07864 Da
IUPAC Name(2R,3S)-2-hydroxy-3-methylpentanoic acid
Traditional NameHMVA
CAS Registry NumberNot Available
SMILES
CC[C@H](C)[C@@H](O)C(O)=O
InChI Identifier
InChI=1S/C6H12O3/c1-3-4(2)5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t4-,5+/m0/s1
InChI KeyRILPIWOPNGRASR-CRCLSJGQSA-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
Nicotiana tabacumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentHydroxy fatty acids  
Alternative Parents
Substituents
  • Branched fatty acid
    • 

  • Methyl-branched fatty acid
    • 

  • Hydroxy fatty acid
    • 

  • Alpha-hydroxy acid
    • 

  • Hydroxy acid
    • 

  • Monosaccharide
    • 

  • Secondary alcohol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • 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
logP0.86ChemAxon
pKa (Strongest Acidic)4.25ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.44 m³·mol⁻¹ChemAxon
Polarizability13.71 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 IDNot Available
Chemspider ID8995864  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10820562  
PDB IDNot Available
ChEBI ID55536  
Good Scents IDNot Available
References
General References
  1. Mamer OA, Reimer ML: On the mechanisms of the formation of L-alloisoleucine and the 2-hydroxy-3-methylvaleric acid stereoisomers from L-isoleucine in maple syrup urine disease patients and in normal humans. J Biol Chem. 1992 Nov 5;267(31):22141-7. [PubMed:1429566  ] 
  2. LOTUS database [Link]