Showing NP-Card for Caprylic acid (NP0000406)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-01-12 19:25:50 UTC
NP-MRD IDNP0000406
Secondary Accession NumbersNone
Natural Product Identification
Common NameCaprylic acid
DescriptionCaprylic acid is the common name for the eight-carbon straight-chain fatty acid known by the systematic name octanoic acid. It is found naturally in coconuts and breast milk. It is an oily liquid with a slightly unpleasant rancid taste that is minimally soluble in water. Caprylic acid is used commercially in the production of esters used in perfumery and also in the manufacture of dyes (Wikipedia).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000406 (Caprylic acid)

  Mrv1652309272007422D          

 10  9  0  0  0  0            999 V2000
   -0.5845   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0159   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5605   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2743   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297    0.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4434   -0.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
M  END
Download

3D MOL for NP0000406 (Caprylic acid)

HMDB0000482
     RDKit          3D
Caprylic acid
 26 25  0  0  0  0  0  0  0  0999 V2000
   -4.2791   -0.3245    0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555    0.4935   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8643   -0.1270    0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6519    0.5826   -0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5677   -0.1542    0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486    0.4794   -0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9933   -0.3033    0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2956    0.2634   -0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3543   -0.2600    0.3313 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789    1.3454   -0.9198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1311   -1.3797    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0569   -0.3404    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2648    0.0601    0.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1991    0.4750   -1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2649    1.5261    0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8432   -1.1626   -0.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -0.1414    1.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5660    1.6222    0.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6150    0.5769   -1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4604   -1.1969   -0.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750   -0.1183    1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8563    0.3215   -1.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8933    1.5501   -0.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9273   -0.1824    1.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8821   -1.3584    0.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454    1.1969   -1.8579 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
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
M  END
Download

3D SDF for NP0000406 (Caprylic acid)

  Mrv1652309272007422D          

 10  9  0  0  0  0            999 V2000
   -0.5845   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0159   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5605   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297   -0.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2743   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7297    0.3038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4434   -0.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000406

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)

> <INCHI_KEY>
WWZKQHOCKIZLMA-UHFFFAOYSA-N

> <FORMULA>
C8H16O2

> <MOLECULAR_WEIGHT>
144.2114

> <EXACT_MASS>
144.115029756

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.404174014251353

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
octanoic acid

> <ALOGPS_LOGP>
2.92

> <JCHEM_LOGP>
2.700033457666666

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.192975275996319

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
40.275600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
caprylic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000406 (Caprylic acid)

HMDB0000482
     RDKit          3D
Caprylic acid
 26 25  0  0  0  0  0  0  0  0999 V2000
   -4.2791   -0.3245    0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555    0.4935   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8643   -0.1270    0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6519    0.5826   -0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5677   -0.1542    0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486    0.4794   -0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9933   -0.3033    0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2956    0.2634   -0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3543   -0.2600    0.3313 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789    1.3454   -0.9198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1311   -1.3797    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0569   -0.3404    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2648    0.0601    0.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1991    0.4750   -1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2649    1.5261    0.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8432   -1.1626   -0.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7866   -0.1414    1.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5660    1.6222    0.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6150    0.5769   -1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4604   -1.1969   -0.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750   -0.1183    1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8563    0.3215   -1.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8933    1.5501   -0.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9273   -0.1824    1.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8821   -1.3584    0.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454    1.1969   -1.8579 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
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
M  END
Download

PDB for NP0000406 (Caprylic acid)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.091  -1.743   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.241  -0.970   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.431  -0.970   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.573  -1.743   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.763  -1.743   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.913  -0.970   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.095  -0.970   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.245  -1.743   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.095   0.567   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -6.428  -1.750   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9   10                                                  
CONECT    8    6                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
Download

3D PDB for NP0000406 (Caprylic acid)

COMPND    HMDB0000482
HETATM    1  C1  UNL     1      -4.279  -0.324   0.419  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.155   0.494  -0.224  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.864  -0.127   0.255  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.652   0.583  -0.304  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.568  -0.154   0.267  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.849   0.479  -0.233  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.993  -0.303   0.374  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.296   0.263  -0.074  1.00  0.00           C  
HETATM    9  O1  UNL     1       5.354  -0.260   0.331  1.00  0.00           O  
HETATM   10  O2  UNL     1       4.379   1.345  -0.920  1.00  0.00           O  
HETATM   11  H1  UNL     1      -4.131  -1.380   0.048  1.00  0.00           H  
HETATM   12  H2  UNL     1      -4.057  -0.340   1.505  1.00  0.00           H  
HETATM   13  H3  UNL     1      -5.265   0.060   0.165  1.00  0.00           H  
HETATM   14  H4  UNL     1      -3.199   0.475  -1.315  1.00  0.00           H  
HETATM   15  H5  UNL     1      -3.265   1.526   0.201  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.843  -1.163  -0.127  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.787  -0.141   1.345  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.566   1.622   0.028  1.00  0.00           H  
HETATM   19  H9  UNL     1      -0.615   0.577  -1.406  1.00  0.00           H  
HETATM   20  H10 UNL     1       0.460  -1.197  -0.053  1.00  0.00           H  
HETATM   21  H11 UNL     1       0.475  -0.118   1.370  1.00  0.00           H  
HETATM   22  H12 UNL     1       1.856   0.322  -1.342  1.00  0.00           H  
HETATM   23  H13 UNL     1       1.893   1.550  -0.029  1.00  0.00           H  
HETATM   24  H14 UNL     1       2.927  -0.182   1.466  1.00  0.00           H  
HETATM   25  H15 UNL     1       2.882  -1.358   0.112  1.00  0.00           H  
HETATM   26  H16 UNL     1       4.745   1.197  -1.858  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4   16   17
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8   24   25
CONECT    8    9    9   10
CONECT   10   26
END
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SMILES for NP0000406 (Caprylic acid)

CCCCCCCC(O)=O
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INCHI for NP0000406 (Caprylic acid)

InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
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View in JSmol
Synonyms
Chemical FormulaC8H16O2
Average Mass144.2114 Da
Monoisotopic Mass144.11503 Da
IUPAC Nameoctanoic acid
Traditional Namecaprylic acid
CAS Registry Number124-07-2
SMILES
CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
InChI KeyWWZKQHOCKIZLMA-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-12View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Ganoderma lucidumKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point16.5 °CNot Available
Boiling Point237.00 to 239.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.79 mg/mLNot Available
LogP3.05Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility0.91 g/LALOGPS
logP2.92ALOGPS
logP2.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)5.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity40.28 m³·mol⁻¹ChemAxon
Polarizability17.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000482
DrugBank IDDB04519
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006235
KNApSAcK IDC00001231
Chemspider ID370
KEGG Compound IDC06423
BioCyc IDCPD-195
BiGG ID48223
Wikipedia LinkCaprylic_acid
METLIN ID5469
PubChem Compound379
PDB IDNot Available
ChEBI ID28837
Good Scents IDrw1009091
References
General References
  1. Giannakou SA, Dallas PP, Rekkas DM, Choulis NH: In vitro evaluation of nimodipine permeation through human epidermis using response surface methodology. Int J Pharm. 2002 Jul 8;241(1):27-34. [PubMed:12086718 ]
  2. Nair MK, Joy J, Venkitanarayanan KS: Inactivation of Enterobacter sakazakii in reconstituted infant formula by monocaprylin. J Food Prot. 2004 Dec;67(12):2815-9. [PubMed:15633694 ]
  3. Habeeb AF, Francis RD: Preparation of human immunoglobulin by caprylic acid precipitation. Prep Biochem. 1984;14(1):1-17. [PubMed:6718324 ]
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