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Showing NP-Card for 3-Hydroxyoctanoic acid (NP0086822)

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Record Information
Version2.0
Created at2022-05-11 16:31:59 UTC
Updated at2022-05-11 16:31:59 UTC
NP-MRD IDNP0086822
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Hydroxyoctanoic acid
Description3-Hydroxyoctanoic acid, also known as 3-hydroxy-octanoate or 3-OH-caprylic 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. 3-Hydroxyoctanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Hydroxyoctanoic acid was first documented in 1988 (PMID: 3168281). In humans, 3-hydroxyoctanoic acid is involved in fatty acid biosynthesis (PMID: 18422622) (PMID: 19047387).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086822 (3-Hydroxyoctanoic acid)


  Mrv0541 02231219172D          

 11 10  0  0  0  0            999 V2000
    9.1213   -8.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4069   -8.8131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1213   -7.5757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8358   -8.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5503   -8.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4081   -8.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6936   -8.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2647   -8.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9791   -8.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1225   -8.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5503   -7.5757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  8  5  1  0  0  0  0
  7  6  1  0  0  0  0
 10  6  1  0  0  0  0
  9  7  1  0  0  0  0
  9  8  1  0  0  0  0
 11  5  1  0  0  0  0
M  END
Download

3D MOL for NP0086822 (3-Hydroxyoctanoic acid)

     RDKit          3D

 27 26  0  0  0  0  0  0  0  0999 V2000
    4.0792   -0.3629    0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6755    0.1366    0.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9865   -0.6765   -0.9596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5836   -0.1720   -1.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2645   -0.2584    0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6366    0.2683   -0.3104 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2068   -0.4842   -1.3218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5060    0.3422    0.9193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8600    0.8527    0.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2534    1.1880   -0.5121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7471    0.9621    1.6833 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5530   -0.5600   -0.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1234   -1.2143    1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6507    0.4708    0.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1224    0.0812    1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7492    1.1982   -0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5602   -0.5311   -1.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081   -1.7576   -0.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061    0.8642   -1.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0620   -0.7621   -1.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3718   -1.3065    0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184    0.3954    0.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4998    1.3053   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854   -1.4136   -1.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5456   -0.6332    1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0387    1.0593    1.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0629    0.0641    2.0768 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
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  6
  7 24  1  0
  8 25  1  0
  8 26  1  0
 11 27  1  0
M  END
Download

3D SDF for NP0086822 (3-Hydroxyoctanoic acid)


  Mrv0541 02231219172D          

 11 10  0  0  0  0            999 V2000
    9.1213   -8.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4069   -8.8131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1213   -7.5757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8358   -8.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5503   -8.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4081   -8.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6936   -8.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2647   -8.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9791   -8.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1225   -8.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5503   -7.5757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  8  5  1  0  0  0  0
  7  6  1  0  0  0  0
 10  6  1  0  0  0  0
  9  7  1  0  0  0  0
  9  8  1  0  0  0  0
 11  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086822

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H16O3/c1-2-3-4-5-7(9)6-8(10)11/h7,9H,2-6H2,1H3,(H,10,11)

> <INCHI_KEY>
NDPLAKGOSZHTPH-UHFFFAOYSA-N

> <FORMULA>
C8H16O3

> <MOLECULAR_WEIGHT>
160.2108

> <EXACT_MASS>
160.109944378

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.136702266857228

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxyoctanoic acid

> <ALOGPS_LOGP>
1.44

> <JCHEM_LOGP>
1.4692223906666668

> <ALOGPS_LOGS>
-1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.288498485482194

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.83879184641206

> <JCHEM_PKA_STRONGEST_BASIC>
-2.798587340234124

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
41.79109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+/-)-3-hydroxyoctanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0086822 (3-Hydroxyoctanoic acid)

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PDB for NP0086822 (3-Hydroxyoctanoic acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      17.026 -15.681   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      15.693 -16.451   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      17.026 -14.141   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      18.360 -16.451   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.694 -15.681   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.028 -15.681   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.695 -16.451   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.027 -16.451   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.361 -15.681   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.362 -16.451   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      19.694 -14.141   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5                                                       
CONECT    5    4    8   11                                                  
CONECT    6    7   10                                                       
CONECT    7    6    9                                                       
CONECT    8    5    9                                                       
CONECT    9    7    8                                                       
CONECT   10    6                                                            
CONECT   11    5                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0086822 (3-Hydroxyoctanoic acid)
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SMILES for NP0086822 (3-Hydroxyoctanoic acid)
CCCCCC(O)CC(O)=O
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INCHI for NP0086822 (3-Hydroxyoctanoic acid)
InChI=1S/C8H16O3/c1-2-3-4-5-7(9)6-8(10)11/h7,9H,2-6H2,1H3,(H,10,11)
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View in JSmol
Synonyms
ValueSource
3-Hydroxy-octanoic acidChEBI
3-Hydroxycaprylic acidChEBI
3-OH Octanoic acidChEBI
3-OH-Caprylic acidChEBI
3HOChEBI
beta-Hydroxycaprylic acidChEBI
beta-Hydroxyoctanoic acidChEBI
beta-OH-Caprylic acidChEBI
beta-OH-Octanoic acidChEBI
3-Hydroxy-octanoateGenerator
3-HydroxycaprylateGenerator
3-OH OctanoateGenerator
3-OH-CaprylateGenerator
b-HydroxycaprylateGenerator
b-Hydroxycaprylic acidGenerator
beta-HydroxycaprylateGenerator
Β-hydroxycaprylateGenerator
Β-hydroxycaprylic acidGenerator
b-HydroxyoctanoateGenerator
b-Hydroxyoctanoic acidGenerator
beta-HydroxyoctanoateGenerator
Β-hydroxyoctanoateGenerator
Β-hydroxyoctanoic acidGenerator
b-OH-CaprylateGenerator
b-OH-Caprylic acidGenerator
beta-OH-CaprylateGenerator
Β-OH-caprylateGenerator
Β-OH-caprylic acidGenerator
b-OH-OctanoateGenerator
b-OH-Octanoic acidGenerator
beta-OH-OctanoateGenerator
Β-OH-octanoateGenerator
Β-OH-octanoic acidGenerator
3-HydroxyoctanoateGenerator
(+/-)-3-hydroxyoctanoateHMDB
(+/-)-3-hydroxyoctanoic acidHMDB
3-Hydroxy caprylic acidHMDB
3-Hydroxyoctanoic acid homopolymerHMDB
8:0(3-OH)HMDB
Poly-3-hydroxyoctanoateHMDB
Poly-3-hydroxyoctanoic acidHMDB
3-Hydroxyoctanoic acid, (S)-isomerHMDB
3-Hydroxy caprylateHMDB
3-Hydroxyoctanoic acidMeSH
Chemical FormulaC8H16O3
Average Mass160.2108 Da
Monoisotopic Mass160.10994 Da
IUPAC Name3-hydroxyoctanoic acid
Traditional Name(+/-)-3-hydroxyoctanoic acid
CAS Registry NumberNot Available
SMILES
CCCCCC(O)CC(O)=O
InChI Identifier
InChI=1S/C8H16O3/c1-2-3-4-5-7(9)6-8(10)11/h7,9H,2-6H2,1H3,(H,10,11)
InChI KeyNDPLAKGOSZHTPH-UHFFFAOYSA-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
logP1.44ALOGPS
logP1.47ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.84ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity41.79 m³·mol⁻¹ChemAxon
Polarizability18.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001954  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022761  
KNApSAcK IDNot Available
Chemspider ID24791  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Hydroxyoctanoic acid  
METLIN IDNot Available
PubChem Compound26613  
PDB IDNot Available
ChEBI ID37098  
Good Scents IDNot Available
References
General References
  1. Yuan MQ, Shi ZY, Wei XX, Wu Q, Chen SF, Chen GQ: Microbial production of medium-chain-length 3-hydroxyalkanoic acids by recombinant Pseudomonas putida KT2442 harboring genes fadL, fadD and phaZ. FEMS Microbiol Lett. 2008 Jun;283(2):167-75. doi:  10.1111/j.1574-6968.2008.01164.x. Epub 2008 Apr 16. [PubMed:18422622  ] 
  2. Elbahloul Y, Steinbuchel A: Large-scale production of poly(3-hydroxyoctanoic acid) by Pseudomonas putida GPo1 and a simplified downstream process. Appl Environ Microbiol. 2009 Feb;75(3):643-51. doi: 10.1128/AEM.01869-08. Epub  2008 Dec 1. [PubMed:19047387  ] 
  3. Kelley RI, Morton DH: 3-Hydroxyoctanoic aciduria: identification of a new organic acid in the urine of a patient with non-ketotic hypoglycemia. Clin Chim Acta. 1988 Jun 30;175(1):19-26. doi: 10.1016/0009-8981(88)90031-9. [PubMed:3168281  ]