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Showing NP-Card for Dihydrojasmonic acid (NP0047682)

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Record Information
Version1.0
Created at2022-03-17 20:44:12 UTC
Updated at2022-03-17 20:44:12 UTC
NP-MRD IDNP0047682
Secondary Accession NumbersNone
Natural Product Identification
Common NameDihydrojasmonic acid
DescriptionDihydrojasmonic acid, also known as dihydrojasmonate, belongs to the class of organic compounds known as jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety. Dihydrojasmonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Dihydrojasmonic acid has been detected, but not quantified in, several different foods, such as broad beans, cereals and cereal products, pulses, and ryes. Dihydrojasmonic acid is found in Lasiodiplodia theobromae, Secale cereale and Vicia faba,Secale cereale. It was first documented in 2000 (PMID: 11413487). This could make dihydrojasmonic acid a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047682 (Dihydrojasmonic acid)


  Mrv0541 05061307132D          

 15 15  0  0  0  0            999 V2000
    0.6725    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3870    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5506    3.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1381    4.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1701    2.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9986    2.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3311    4.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9547    1.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7180    4.6057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5678    2.3878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1262    1.0288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  2  0  0  0  0
 15 12  1  0  0  0  0
M  END
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3D MOL for NP0047682 (Dihydrojasmonic acid)

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3D SDF for NP0047682 (Dihydrojasmonic acid)

  Mrv0541 05061307132D          

 15 15  0  0  0  0            999 V2000
    0.6725    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3870    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5506    3.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1381    4.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1701    2.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9986    2.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449    3.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3311    4.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9547    1.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7180    4.6057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5678    2.3878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1262    1.0288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  2  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047682

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC1C(CC(O)=O)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h9-10H,2-8H2,1H3,(H,14,15)

> <INCHI_KEY>
PQEYTAGBXNEUQL-UHFFFAOYSA-N

> <FORMULA>
C12H20O3

> <MOLECULAR_WEIGHT>
212.2854

> <EXACT_MASS>
212.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.083800153826225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-oxo-2-pentylcyclopentyl)acetic acid

> <ALOGPS_LOGP>
2.67

> <JCHEM_LOGP>
2.776232534333333

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.766814637921793

> <JCHEM_PKA_STRONGEST_BASIC>
-7.416685251818894

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
57.43990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3-oxo-2-pentylcyclopentyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047682 (Dihydrojasmonic acid)
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PDB for NP0047682 (Dihydrojasmonic 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       1.255   5.265   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.589   6.035   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.923   5.265   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.256   6.035   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.590   5.265   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.361   6.553   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.591   7.887   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.651   3.903   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.331   5.409   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.924   6.035   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.085   7.567   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.115   3.427   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.940   8.597   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      12.260   4.457   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      11.436   1.920   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4   10                                                       
CONECT    6    7    9                                                       
CONECT    7    6   11                                                       
CONECT    8    9   12                                                       
CONECT    9    6    8   10                                                  
CONECT   10    5    9   11                                                  
CONECT   11    7   10   13                                                  
CONECT   12    8   14   15                                                  
CONECT   13   11                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

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3D PDB for NP0047682 (Dihydrojasmonic acid)
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SMILES for NP0047682 (Dihydrojasmonic acid)
CCCCCC1C(CC(O)=O)CCC1=O
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INCHI for NP0047682 (Dihydrojasmonic acid)
InChI=1S/C12H20O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h9-10H,2-8H2,1H3,(H,14,15)
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View in JSmol
Synonyms
ValueSource
DihydrojasmonateGenerator
(-)-9,10-Dihydrojasmonic acidHMDB
(-)-Dihydrojasmonic acidHMDB
2-[(1R,2R)-3-oxo-2-Pentylcyclopentyl]acetic acidHMDB
3-oxo-2-Pentyl-(1R-trans)-cyclopentaneacetic acidHMDB
9,10-Dihydrojasmonic acidHMDB
Cyclopentaneacetic acid, 3-oxo-2-pentyl-, (1R,2R)- (9ci)HMDB
[(1R,2R)-3-oxo-2-Pentylcyclopentyl]acetic acidHMDB
2-(3-oxo-2-Pentylcyclopentyl)acetateGenerator
Chemical FormulaC12H20O3
Average Mass212.2854 Da
Monoisotopic Mass212.14124 Da
IUPAC Name2-(3-oxo-2-pentylcyclopentyl)acetic acid
Traditional Name(3-oxo-2-pentylcyclopentyl)acetic acid
CAS Registry Number98674-52-3
SMILES
CCCCCC1C(CC(O)=O)CCC1=O
InChI Identifier
InChI=1S/C12H20O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h9-10H,2-8H2,1H3,(H,14,15)
InChI KeyPQEYTAGBXNEUQL-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lasiodiplodia theobromaeLOTUS Database
Secale cerealePlant
Vicia fabaFooDB
Vicia faba,Secale cerealePlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassLineolic acids and derivatives  
Direct ParentJasmonic acids  
Alternative Parents
Substituents
  • Jasmonic acid
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
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
logP2.67ALOGPS
logP2.78ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)4.77ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity57.44 m³·mol⁻¹ChemAxon
Polarizability24.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033601  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011689  
KNApSAcK IDC00000225  
Chemspider ID96397  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound107126  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487  ] 
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246  ] 
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880  ] 
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567  ]