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Showing NP-Card for 11-Hydroxyjasmonic acid (NP0050224)

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Record Information
Version2.0
Created at2022-04-27 20:48:51 UTC
Updated at2022-04-27 20:48:51 UTC
NP-MRD IDNP0050224
Secondary Accession NumbersNone
Natural Product Identification
Common Name11-Hydroxyjasmonic acid
Description(11R)-(?)-11-Hydroxyjasmonic acid 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. 11-Hydroxyjasmonic acid is found in Lasiodiplodia theobromae and Solanum demissum. Based on a literature review very few articles have been published on (11R)-(?)-11-Hydroxyjasmonic acid.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050224 (11-Hydroxyjasmonic acid)


  Mrv1652304272222482D          

 16 16  0  0  1  0            999 V2000
    0.5678    1.1143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  2  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
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175    0.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    1.3942    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3737    1.6491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    1.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  1  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  1  0  0  0
 10 12  1  0  0  0  0
  1 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
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3D MOL for NP0050224 (11-Hydroxyjasmonic acid)

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3D SDF for NP0050224 (11-Hydroxyjasmonic acid)

  Mrv1652304272222482D          

 16 16  0  0  1  0            999 V2000
    0.5678    1.1143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  2  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
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175    0.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    1.3942    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3737    1.6491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    1.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  1  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  1  0  0  0
 10 12  1  0  0  0  0
  1 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050224

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O4/c1-8(13)3-2-4-10-9(7-12(15)16)5-6-11(10)14/h2-3,8-10,13H,4-7H2,1H3,(H,15,16)/b3-2-/t8-,9-,10-/m1/s1

> <INCHI_KEY>
KLPBEXRQJBKPDM-DIALRVQJSA-N

> <FORMULA>
C12H18O4

> <MOLECULAR_WEIGHT>
226.272

> <EXACT_MASS>
226.12050906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
23.835087395408323

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,2R)-2-[(2Z,4R)-4-hydroxypent-2-en-1-yl]-3-oxocyclopentyl]acetic acid

> <ALOGPS_LOGP>
0.67

> <JCHEM_LOGP>
1.1055460806666666

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.92776266827839

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.5362871285481905

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9555952827860295

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
60.149

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.92e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2R)-2-[(2Z,4R)-4-hydroxypent-2-en-1-yl]-3-oxocyclopentyl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0050224 (11-Hydroxyjasmonic acid)
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PDB for NP0050224 (11-Hydroxyjasmonic 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       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.915   0.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.379   1.096   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.700   2.602   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.164   3.078   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.555   3.633   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.393   5.930   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.727   3.620   0.000  0.00  0.00           O+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

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3D PDB for NP0050224 (11-Hydroxyjasmonic acid)
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SMILES for NP0050224 (11-Hydroxyjasmonic acid)
C[C@@H](O)\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O
Download
INCHI for NP0050224 (11-Hydroxyjasmonic acid)
InChI=1S/C12H18O4/c1-8(13)3-2-4-10-9(7-12(15)16)5-6-11(10)14/h2-3,8-10,13H,4-7H2,1H3,(H,15,16)/b3-2-/t8-,9-,10-/m1/s1
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View in JSmol
Synonyms
ValueSource
(11R)-(?)-11-hydroxyjasmonateGenerator
Chemical FormulaC12H18O4
Average Mass226.2720 Da
Monoisotopic Mass226.12051 Da
IUPAC Name2-[(1R,2R)-2-[(2Z,4R)-4-hydroxypent-2-en-1-yl]-3-oxocyclopentyl]acetic acid
Traditional Name[(1R,2R)-2-[(2Z,4R)-4-hydroxypent-2-en-1-yl]-3-oxocyclopentyl]acetic acid
CAS Registry NumberNot Available
SMILES
C[C@@H](O)\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O
InChI Identifier
InChI=1S/C12H18O4/c1-8(13)3-2-4-10-9(7-12(15)16)5-6-11(10)14/h2-3,8-10,13H,4-7H2,1H3,(H,15,16)/b3-2-/t8-,9-,10-/m1/s1
InChI KeyKLPBEXRQJBKPDM-DIALRVQJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lasiodiplodia theobromaeLOTUS Database
Solanum demissumPlant
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
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • 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
logP0.67ALOGPS
logP1.11ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)4.54ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity60.15 m³·mol⁻¹ChemAxon
Polarizability23.84 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15127091  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available