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Showing NP-Card for (R)-3-Hydroxyhexanoic acid (NP0091114)

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Record Information
Version1.0
Created at2022-05-11 18:31:05 UTC
Updated at2022-05-11 18:31:06 UTC
NP-MRD IDNP0091114
Secondary Accession NumbersNone
Natural Product Identification
Common Name(R)-3-Hydroxyhexanoic acid
Description(R)-3-Hydroxyhexanoic acid belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain (R)-3-Hydroxyhexanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (R)-3-Hydroxyhexanoic acid exists in all eukaryotes, ranging from yeast to humans. Within humans, (R)-3-hydroxyhexanoic acid participates in a number of enzymatic reactions. In particular, (R)-3-hydroxyhexanoic acid can be biosynthesized from 3-oxohexanoic acid through the action of the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In addition, (R)-3-hydroxyhexanoic acid can be converted into trans-hex-2-enoic acid through its interaction with the enzyme fatty acid synthase. Dyhydrase domain. ==(R)==-3-Hydroxyhexanoic acid is a fatty acid formed by the action of fatty acid synthases from acetyl-CoA and malonyl-CoA precursors. Specifically, it is the product of reaction between 3-Oxohexanoic acid and 2 enzymes; fatty-acid Synthase and 3-oxoacyl- reductase. In humans, (R)-3-hydroxyhexanoic acid is involved in fatty acid biosynthesis. It is involved in the fatty acid biosynthesis.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0091114 ((R)-3-Hydroxyhexanoic acid)


  Mrv1652310241917282D          

  9  8  0  0  0  0            999 V2000
 9997.9637 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2489 9998.4815    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.5339 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8190 9998.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1042 9998.0698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8190 9999.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2489 9999.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6785 9998.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3942 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  8  9  1  0  0  0  0
M  END
Download

3D MOL for NP0091114 ((R)-3-Hydroxyhexanoic acid)

     RDKit          3D

 21 20  0  0  0  0  0  0  0  0999 V2000
   -2.6235    0.7721    0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8277    0.0936   -0.6468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3472    0.2278   -0.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2229   -0.3275    0.7519 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0702   -1.6800    0.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7149   -0.0344    0.8245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4553   -0.6255   -0.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3613   -1.8357   -0.5638 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2749    0.1986   -1.1036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1741    0.6800    1.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7457    1.8709    0.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6500    0.3498    0.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0916   -0.9935   -0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1813    0.5091   -1.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0422    1.3028   -0.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1479   -0.2934   -1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2347    0.1979    1.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7238   -2.2124    1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8331    1.0558    0.8792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1197   -0.4606    1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1343    1.2045   -1.1266 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
  4  5  1  0
  4  6  1  0
  6  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  0
  3 16  1  0
  4 17  1  1
  5 18  1  0
  6 19  1  0
  6 20  1  0
  9 21  1  0
M  END
Download

3D SDF for NP0091114 ((R)-3-Hydroxyhexanoic acid)


  Mrv1652310241917282D          

  9  8  0  0  0  0            999 V2000
 9997.9637 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2489 9998.4815    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.5339 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8190 9998.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1042 9998.0698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8190 9999.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2489 9999.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6785 9998.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3942 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0091114

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O3/c1-2-3-5(7)4-6(8)9/h5,7H,2-4H2,1H3,(H,8,9)/t5-/m1/s1

> <INCHI_KEY>
HPMGFDVTYHWBAG-RXMQYKEDSA-N

> <FORMULA>
C6H12O3

> <MOLECULAR_WEIGHT>
132.1577

> <EXACT_MASS>
132.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
13.870108062232962

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-hydroxyhexanoic acid

> <ALOGPS_LOGP>
0.57

> <JCHEM_LOGP>
0.5800850606666665

> <ALOGPS_LOGS>
0.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.288991049395367

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.67423988970905

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7983718893851792

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
32.5891

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3R-hydroxy-hexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0091114 ((R)-3-Hydroxyhexanoic acid)

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PDB for NP0091114 ((R)-3-Hydroxyhexanoic acid)
HEADER    PROTEIN                                 24-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-OCT-19         0                                  
HETATM    1  C   UNK     0    8662.8668663.064   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8661.5318663.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8660.1978663.064   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8658.8628663.832   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8657.5288663.064   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8658.8628665.373   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8661.5318665.373   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8664.2008663.832   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.5368663.064   0.000  0.00  0.00           C+0
CONECT    1    2    8                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2                                                            
CONECT    8    1    9                                                       
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0091114 ((R)-3-Hydroxyhexanoic acid)
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SMILES for NP0091114 ((R)-3-Hydroxyhexanoic acid)
CCC[C@@H](O)CC(O)=O
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INCHI for NP0091114 ((R)-3-Hydroxyhexanoic acid)
InChI=1S/C6H12O3/c1-2-3-5(7)4-6(8)9/h5,7H,2-4H2,1H3,(H,8,9)/t5-/m1/s1
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View in JSmol
Synonyms
ValueSource
(R)-3-HydroxyhexanoateGenerator
(3R)-3-HydroxyhexanoateHMDB
(3R)-3-Hydroxyhexanoic acidHMDB
(R)-3-Hydroxyhexanoic acidHMDB
(±)-3-HydroxyhexanoateHMDB
(±)-3-Hydroxyhexanoic acidHMDB
3-HydroxycaproateHMDB
3-Hydroxycaproic acidHMDB
3-HydroxyhexanoateHMDB
3-Hydroxyhexanoic acidHMDB
D-beta-HydroxycaproateHMDB
D-beta-Hydroxycaproic acidHMDB
D-β-HydroxycaproateHMDB
D-β-Hydroxycaproic acidHMDB
FA(6:0(3-OH))HMDB
FA(6:0(3R-OH))HMDB
beta-Hydroxy-n-caproateHMDB
beta-Hydroxy-n-caproic acidHMDB
beta-HydroxycaproateHMDB
beta-Hydroxycaproic acidHMDB
beta-HydroxyhexanoateHMDB
beta-Hydroxyhexanoic acidHMDB
β-Hydroxy-n-caproateHMDB
β-Hydroxy-n-caproic acidHMDB
β-HydroxycaproateHMDB
β-Hydroxycaproic acidHMDB
β-HydroxyhexanoateHMDB
β-Hydroxyhexanoic acidHMDB
Chemical FormulaC6H12O3
Average Mass132.1577 Da
Monoisotopic Mass132.07864 Da
IUPAC Name(3R)-3-hydroxyhexanoic acid
Traditional Name3R-hydroxy-hexanoic acid
CAS Registry NumberNot Available
SMILES
CCC[C@@H](O)CC(O)=O
InChI Identifier
InChI=1S/C6H12O3/c1-2-3-5(7)4-6(8)9/h5,7H,2-4H2,1H3,(H,8,9)/t5-/m1/s1
InChI KeyHPMGFDVTYHWBAG-RXMQYKEDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassHydroxy acids and derivatives  
Sub ClassMedium-chain hydroxy acids and derivatives  
Direct ParentMedium-chain hydroxy acids and derivatives  
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
    • 

  • Medium-chain fatty acid
    • 

  • Beta-hydroxy acid
    • 

  • Hydroxy fatty acid
    • 

  • Fatty acyl
    • 

  • Fatty acid
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP0.57ALOGPS
logP0.58ChemAxon
logS0ALOGPS
pKa (Strongest Acidic)4.67ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.59 m³·mol⁻¹ChemAxon
Polarizability13.87 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0010718  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027868  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10197713  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available