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Showing NP-Card for 9-Hydroxynonanoic acid (NP0047049)

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Record Information
Version2.0
Created at2022-03-17 20:33:46 UTC
Updated at2022-03-17 20:33:46 UTC
NP-MRD IDNP0047049
Secondary Accession NumbersNone
Natural Product Identification
Common Name9-Hydroxynonanoic acid
Description9-Hydroxynonanoic acid, also known as 9-hydroxy pelargonic acid or omega-hydroxynonanoate, 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. An omega-hydroxy fatty acid that is nonanoic acid in which one of the hydrogens of the terminal methyl group is replaced by a hydroxy group. 9-Hydroxynonanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 9-Hydroxynonanoic acid has been detected, but not quantified in, potato. 9-Hydroxynonanoic acid is found in Chaenomeles sinensis. 9-Hydroxynonanoic acid was first documented in 2008 (PMID: 18271512). This could make 9-hydroxynonanoic acid a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047049 (9-Hydroxynonanoic acid)


  Mrv1652310091719052D          

 12 11  0  0  0  0            999 V2000
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
M  END
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3D MOL for NP0047049 (9-Hydroxynonanoic acid)

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3D SDF for NP0047049 (9-Hydroxynonanoic acid)

  Mrv1652310091719052D          

 12 11  0  0  0  0            999 V2000
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047049

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H18O3/c10-8-6-4-2-1-3-5-7-9(11)12/h10H,1-8H2,(H,11,12)

> <INCHI_KEY>
AFZMICRBFKZNIH-UHFFFAOYSA-N

> <FORMULA>
C9H18O3

> <MOLECULAR_WEIGHT>
174.2374

> <EXACT_MASS>
174.125594442

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
20.521908366663347

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxynonanoic acid

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
1.7079235059999995

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.84394282199191

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.834071795911304

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9922595049014746

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
46.8053

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.92e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy pelargonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047049 (9-Hydroxynonanoic acid)
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PDB for NP0047049 (9-Hydroxynonanoic acid)
HEADER    PROTEIN                                 09-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-OCT-17         0                                  
HETATM    1  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.906   6.105   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      21.243   6.105   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      19.909   3.795   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                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11   12                                                  
CONECT   10    8                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0047049 (9-Hydroxynonanoic acid)
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SMILES for NP0047049 (9-Hydroxynonanoic acid)
OCCCCCCCCC(O)=O
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INCHI for NP0047049 (9-Hydroxynonanoic acid)
InChI=1S/C9H18O3/c10-8-6-4-2-1-3-5-7-9(11)12/h10H,1-8H2,(H,11,12)
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Synonyms
ValueSource
9-Hydroxy pelargonic acidChEBI
9-Hydroxypelargonic acidChEBI
Omega-hydroxynonanoic acidChEBI
9-Hydroxy pelargonateGenerator
9-HydroxypelargonateGenerator
Omega-hydroxynonanoateGenerator
9-HydroxynonanoateGenerator
Chemical FormulaC9H18O3
Average Mass174.2374 Da
Monoisotopic Mass174.12559 Da
IUPAC Name9-hydroxynonanoic acid
Traditional Name9-hydroxy pelargonic acid
CAS Registry Number3788-56-5
SMILES
OCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C9H18O3/c10-8-6-4-2-1-3-5-7-9(11)12/h10H,1-8H2,(H,11,12)
InChI KeyAFZMICRBFKZNIH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Chaenomeles sinensisLOTUS Database
Solanum tuberosumFooDB
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
    • 

  • Hydroxy fatty acid
    • 

  • Straight chain fatty acid
    • 

  • Fatty acyl
    • 

  • Fatty acid
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Primary alcohol
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP1.95ALOGPS
logP1.71ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)4.83ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity46.81 m³·mol⁻¹ChemAxon
Polarizability20.52 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0170939  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007087  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound138052  
PDB IDNot Available
ChEBI ID79121  
Good Scents IDNot Available
References
General References
  1. Liu G, Kong X, Wan H, Narine S: Production of 9-hydroxynonanoic Acid from methyl oleate and conversion into lactone monomers for the synthesis of biodegradable polylactones. Biomacromolecules. 2008 Mar;9(3):949-53. doi: 10.1021/bm7012235. Epub 2008 Feb 14. [PubMed:18271512  ]