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Showing NP-Card for (+)-4,5-Didehydrojasmonic acid (NP0050226)

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Record Information
Version2.0
Created at2022-04-27 20:48:55 UTC
Updated at2022-04-27 20:48:55 UTC
NP-MRD IDNP0050226
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-4,5-Didehydrojasmonic acid
Description(1S)-4-Oxo-5beta-[(Z)-2-pentenyl]-2-cyclopentene-1beta-acetic acid belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. (+)-4,5-Didehydrojasmonic acid is found in Equisetum sylvaticum and Lasiodiplodia theobromae. Based on a literature review very few articles have been published on (1S)-4-Oxo-5beta-[(Z)-2-pentenyl]-2-cyclopentene-1beta-acetic acid.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050226 ((+)-4,5-Didehydrojasmonic acid)


  Mrv1652304272222482D          

 15 15  0  0  1  0            999 V2000
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8405    1.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4535    1.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2382    1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -1.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857    0.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  4  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
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3D MOL for NP0050226 ((+)-4,5-Didehydrojasmonic acid)

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3D SDF for NP0050226 ((+)-4,5-Didehydrojasmonic acid)

  Mrv1652304272222482D          

 15 15  0  0  1  0            999 V2000
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8405    1.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4535    1.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2382    1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -1.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857    0.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  4  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050226

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/C[C@H]1[C@@H](CC(O)=O)C=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,6-7,9-10H,2,5,8H2,1H3,(H,14,15)/b4-3-/t9-,10+/m1/s1

> <INCHI_KEY>
KJWUKJXAYNQYSS-QKMQQOOLSA-N

> <FORMULA>
C12H16O3

> <MOLECULAR_WEIGHT>
208.257

> <EXACT_MASS>
208.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
22.112831264429516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl]acetic acid

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
2.4121343673333335

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.778878121552403

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.657190055454789

> <JCHEM_PKA_STRONGEST_BASIC>
-5.006368594567296

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
59.6498

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0050226 ((+)-4,5-Didehydrojasmonic acid)
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PDB for NP0050226 ((+)-4,5-Didehydrojasmonic acid)
HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.971   3.157   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.436   3.633   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.580   2.602   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.045   3.078   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.147  -1.375   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.052  -2.621   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -2.773   0.032   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    3   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

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3D PDB for NP0050226 ((+)-4,5-Didehydrojasmonic acid)
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SMILES for NP0050226 ((+)-4,5-Didehydrojasmonic acid)
CC\C=C/C[C@H]1[C@@H](CC(O)=O)C=CC1=O
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INCHI for NP0050226 ((+)-4,5-Didehydrojasmonic acid)
InChI=1S/C12H16O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,6-7,9-10H,2,5,8H2,1H3,(H,14,15)/b4-3-/t9-,10+/m1/s1
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View in JSmol
Synonyms
ValueSource
(1S)-4-oxo-5b-[(Z)-2-Pentenyl]-2-cyclopentene-1b-acetateGenerator
(1S)-4-oxo-5b-[(Z)-2-Pentenyl]-2-cyclopentene-1b-acetic acidGenerator
(1S)-4-oxo-5beta-[(Z)-2-Pentenyl]-2-cyclopentene-1beta-acetateGenerator
(1S)-4-oxo-5Β-[(Z)-2-pentenyl]-2-cyclopentene-1β-acetateGenerator
(1S)-4-oxo-5Β-[(Z)-2-pentenyl]-2-cyclopentene-1β-acetic acidGenerator
Chemical FormulaC12H16O3
Average Mass208.2570 Da
Monoisotopic Mass208.10994 Da
IUPAC Name2-[(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl]acetic acid
Traditional Name[(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl]acetic acid
CAS Registry NumberNot Available
SMILES
CC\C=C/C[C@H]1[C@@H](CC(O)=O)C=CC1=O
InChI Identifier
InChI=1S/C12H16O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,6-7,9-10H,2,5,8H2,1H3,(H,14,15)/b4-3-/t9-,10+/m1/s1
InChI KeyKJWUKJXAYNQYSS-QKMQQOOLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Equisetum sylvaticumPlant
Lasiodiplodia theobromaeLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentCyclic ketones  
Alternative Parents
Substituents
  • Cyclic ketone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP2.39ALOGPS
logP2.41ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)4.66ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity59.65 m³·mol⁻¹ChemAxon
Polarizability22.11 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID75143079  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14311113  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available