Np mrd loader

Showing NP-Card for Citronellic acid (NP0048349)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-03-17 20:55:03 UTC
Updated at2022-03-17 20:55:03 UTC
NP-MRD IDNP0048349
Secondary Accession NumbersNone
Natural Product Identification
Common NameCitronellic acid
DescriptionCitronellic acid, also known as rhodinic acid or citronellate, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Citronellic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Citronellic acid exists in all living organisms, ranging from bacteria to humans. Citronellic acid is a fatty, floral, and grassy tasting compound. Outside of the human body, Citronellic acid is found, on average, in the highest concentration within lemon balms and peppermints. Citronellic acid has also been detected, but not quantified in, a few different foods, such as cardamoms, lemon grass, and mandarin orange (clementine, tangerine). This could make citronellic acid a potential biomarker for the consumption of these foods. Citronellic acid is found in Callitris glauca, Callitris intratropica, Chamaecyparis obtusa, Daphne papyracea, Eucalyptus albens, Eucalyptus tereticornis, Juniperus spp., Pelargonium graveolens, Pelargonium vitifolium and Thujopsis dolabrata. Citronellic acid was first documented in 1990 (PMID: 2265211). A monounsaturated fatty acid that is oct-6-enoic acid carrying methyl groups at positions 3 and 7 (PMID: 18605213) (PMID: 20429462) (PMID: 20568624) (PMID: 29393872).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0048349 (Citronellic acid)


  Mrv0541 05061308442D          

 12 11  0  0  0  0            999 V2000
    1.0461    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  5  2  0  0  0  0
  9  3  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
M  END
Download

3D MOL for NP0048349 (Citronellic acid)

Download
3D SDF for NP0048349 (Citronellic acid)

  Mrv0541 05061308442D          

 12 11  0  0  0  0            999 V2000
    1.0461    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  5  2  0  0  0  0
  9  3  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048349

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC=C(C)C)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,9H,4,6-7H2,1-3H3,(H,11,12)

> <INCHI_KEY>
GJWSUKYXUMVMGX-UHFFFAOYSA-N

> <FORMULA>
C10H18O2

> <MOLECULAR_WEIGHT>
170.2487

> <EXACT_MASS>
170.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
20.129509141855323

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7-dimethyloct-6-enoic acid

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
2.8684921689999996

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.189657325457579

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
50.22280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
citronellic acid

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0048349 (Citronellic acid)
Download
PDB for NP0048349 (Citronellic acid)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.953   5.747   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620   5.747   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.287   1.127   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.286   4.977   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4    5    6                                                       
CONECT    5    4    8                                                       
CONECT    6    4    9                                                       
CONECT    7    9   10                                                       
CONECT    8    1    2    5                                                  
CONECT    9    3    6    7                                                  
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

Download
3D PDB for NP0048349 (Citronellic acid)
Download
SMILES for NP0048349 (Citronellic acid)
CC(CCC=C(C)C)CC(O)=O
Download
INCHI for NP0048349 (Citronellic acid)
InChI=1S/C10H18O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,9H,4,6-7H2,1-3H3,(H,11,12)
Download
View in JSmol
Synonyms
ValueSource
3,7-Dimethyl-6-octenoic acidChEBI
Rhodinic acidChEBI
Rhodinolic acidChEBI
3,7-Dimethyl-6-octenoateGenerator
RhodinateGenerator
RhodinolateGenerator
CitronellateGenerator
CallitrolHMDB
FEMA 3142HMDB
Chemical FormulaC10H18O2
Average Mass170.2487 Da
Monoisotopic Mass170.13068 Da
IUPAC Name3,7-dimethyloct-6-enoic acid
Traditional Namecitronellic acid
CAS Registry Number502-47-6
SMILES
CC(CCC=C(C)C)CC(O)=O
InChI Identifier
InChI=1S/C10H18O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,9H,4,6-7H2,1-3H3,(H,11,12)
InChI KeyGJWSUKYXUMVMGX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Callitris glaucaPlant
Callitris intratropicaPlant
Chamaecyparis obtusaPlant
Citrus reticulataFooDB
Cymbopogon citratusFooDB
Daphne papyraceaLOTUS Database
Elettaria cardamomumFooDB
Eucalyptus albensLOTUS Database
Eucalyptus tereticornisLOTUS Database
Juniperus spp.Plant
Melissa officinalis L.FooDB
Mentha x piperitaFooDB
Pelargonium graveolensLOTUS Database
Pelargonium vitifoliumLOTUS Database
Thujopsis dolabrataPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentAcyclic monoterpenoids  
Alternative Parents
Substituents
  • Acyclic monoterpenoid
    • 

  • Medium-chain fatty acid
    • 

  • Branched fatty acid
    • 

  • Methyl-branched fatty acid
    • 

  • Unsaturated fatty acid
    • 

  • Fatty acyl
    • 

  • Fatty acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • 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
logP2.88ALOGPS
logP2.87ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)5.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity50.22 m³·mol⁻¹ChemAxon
Polarizability20.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035837  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014607  
KNApSAcK IDNot Available
Chemspider ID9973  
KEGG Compound IDC16462  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10402  
PDB IDNot Available
ChEBI ID80507  
Good Scents IDNot Available
References
General References
  1. Martin A, Armbruster U, Decker D, Gedig T, Kockritz A: Oxidation of citronellal to citronellic acid by molecular oxygen using supported gold catalysts. ChemSusChem. 2008;1(3):242-8. doi: 10.1002/cssc.200700140. [PubMed:18605213  ] 
  2. Phillips AK, Appel AG, Sims SR: Topical toxicity of essential oils to the German cockroach (Dictyoptera: Blattellidae). J Econ Entomol. 2010 Apr;103(2):448-59. doi: 10.1603/EC09192. [PubMed:20429462  ] 
  3. Phillips AK, Appel AG: Fumigant toxicity of essential oils to the German cockroach (Dictyoptera: Blattellidae). J Econ Entomol. 2010 Jun;103(3):781-90. doi: 10.1603/ec09358. [PubMed:20568624  ] 
  4. Berger RG, Akkan Z, Drawert F: Catabolism of geraniol by cell suspension cultures of Citrus limon. Biochim Biophys Acta. 1990 Dec 10;1055(3):234-9. doi: 10.1016/0167-4889(90)90038-f. [PubMed:2265211  ] 
  5. Rychlicka M, Niezgoda N, Gliszczynska A: Lipase-Catalyzed Acidolysis of Egg-Yolk Phosphatidylcholine with Citronellic Acid. New Insight into Synthesis of Isoprenoid-Phospholipids. Molecules. 2018 Feb 2;23(2). pii: molecules23020314. doi: 10.3390/molecules23020314. [PubMed:29393872  ]