NP-MRD: Showing NP-Card for Dihydrojasmonic acid (NP0047682)

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Record Information

Version

2.0

Created at

2022-03-17 20:44:12 UTC

Updated at

2022-03-17 20:44:12 UTC

NP-MRD ID

NP0047682

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydrojasmonic acid

Description

Dihydrojasmonic 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. This could make dihydrojasmonic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  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

$$$$

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

View in JSmol

Synonyms

Value	Source
Dihydrojasmonate	Generator
(-)-9,10-Dihydrojasmonic acid	HMDB
(-)-Dihydrojasmonic acid	HMDB
2-[(1R,2R)-3-oxo-2-Pentylcyclopentyl]acetic acid	HMDB
3-oxo-2-Pentyl-(1R-trans)-cyclopentaneacetic acid	HMDB
9,10-Dihydrojasmonic acid	HMDB
Cyclopentaneacetic acid, 3-oxo-2-pentyl-, (1R,2R)- (9ci)	HMDB
[(1R,2R)-3-oxo-2-Pentylcyclopentyl]acetic acid	HMDB
2-(3-oxo-2-Pentylcyclopentyl)acetate	Generator

Chemical Formula

C₁₂H₂₀O₃

Average Mass

212.2854 Da

Monoisotopic Mass

212.14124 Da

IUPAC Name

2-(3-oxo-2-pentylcyclopentyl)acetic acid

Traditional Name

(3-oxo-2-pentylcyclopentyl)acetic acid

CAS Registry Number

98674-52-3

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 Key

PQEYTAGBXNEUQL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lasiodiplodia theobromae	LOTUS Database	35616633
Secale cereale	Plant	KNApSAcK
Vicia faba	FooDB	KNAPSACK
Vicia faba,Secale cereale	Plant	KNApSAcK

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Jasmonic 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 Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.67	ALOGPS
logP	2.78	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	4.77	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	57.44 m³·mol⁻¹	ChemAxon
Polarizability	24.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033601

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011689

KNApSAcK ID

C00000225

Chemspider ID

96397

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

107126

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Dihydrojasmonic acid (NP0047682)

MOL for NP0047682 (Dihydrojasmonic acid)

3D MOL for NP0047682 (Dihydrojasmonic acid)

3D SDF for NP0047682 (Dihydrojasmonic acid)

3D-SDF for NP0047682 (Dihydrojasmonic acid)

PDB for NP0047682 (Dihydrojasmonic acid)

3D PDB for NP0047682 (Dihydrojasmonic acid)

SMILES for NP0047682 (Dihydrojasmonic acid)

INCHI for NP0047682 (Dihydrojasmonic acid)

Structure for NP0047682 (Dihydrojasmonic acid)

3D Structure for NP0047682 (Dihydrojasmonic acid)