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Showing NP-Card for 12,13-Epoxy-9,15-octadecadienoic acid (NP0336192)

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Record Information
Version2.0
Created at2024-09-11 05:08:59 UTC
Updated at2024-09-11 05:08:59 UTC
NP-MRD IDNP0336192
Secondary Accession NumbersNone
Natural Product Identification
Common Name12,13-Epoxy-9,15-octadecadienoic acid
Description 12,13-Epoxy-9,15-octadecadienoic acid was first documented in 2018 (PMID: 30195166). Based on a literature review a small amount of articles have been published on 12,13-Epoxy-9,15-octadecadienoic acid (PMID: 33947016) (PMID: 32464332).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336192 (12,13-Epoxy-9,15-octadecadienoic acid)


  Mrv2104 05262307412D          

 21 21  0  0  0  0            999 V2000
   15.5862    1.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5862    2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3006    3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7599    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3006    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5862    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8717    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    5.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4592    3.2704    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
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  2  0  0  0  0
 11  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21 16  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
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3D MOL for NP0336192 (12,13-Epoxy-9,15-octadecadienoic acid)

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3D SDF for NP0336192 (12,13-Epoxy-9,15-octadecadienoic acid)

  Mrv2104 05262307412D          

 21 21  0  0  0  0            999 V2000
   15.5862    1.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5862    2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3006    3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7599    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3006    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5862    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8717    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    5.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4592    3.2704    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
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  2  0  0  0  0
 11  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21 16  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336192

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/CC1OC1C\C=C\CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C18H30O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h3,8,10-11,16-17H,2,4-7,9,12-15H2,1H3,(H,19,20)/b10-3-,11-8+

> <INCHI_KEY>
BKKGUKSHPCTUGE-GSRSKSEFNA-N

> <FORMULA>
C18H30O3

> <MOLECULAR_WEIGHT>
294.435

> <EXACT_MASS>
294.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.51803184374084

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9E)-11-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}undec-9-enoic acid

> <JCHEM_LOGP>
5.121958232666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167284180836

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2070915337320205

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
88.0397

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(9E)-11-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}undec-9-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0336192 (12,13-Epoxy-9,15-octadecadienoic acid)
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PDB for NP0336192 (12,13-Epoxy-9,15-octadecadienoic acid)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      29.094   3.588   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.094   5.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.428   5.898   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.552   8.208   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.218   7.438   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.886   7.438   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.885   8.208   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.219   8.208   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.551   7.438   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.428   7.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.553   7.438   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.217   8.208   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.094   8.208   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.887   8.208   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.884   7.438   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.761   7.438   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.221   7.438   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.550   8.208   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.216   7.438   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.550   9.748   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      26.991   6.105   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2   10                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   11                                                       
CONECT    9    7   12                                                       
CONECT   10    3   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   18                                                       
CONECT   16   13   17   21                                                  
CONECT   17   14   16   21                                                  
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

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3D PDB for NP0336192 (12,13-Epoxy-9,15-octadecadienoic acid)
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SMILES for NP0336192 (12,13-Epoxy-9,15-octadecadienoic acid)
CC\C=C/CC1OC1C\C=C\CCCCCCCC(O)=O
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INCHI for NP0336192 (12,13-Epoxy-9,15-octadecadienoic acid)
InChI=1/C18H30O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h3,8,10-11,16-17H,2,4-7,9,12-15H2,1H3,(H,19,20)/b10-3-,11-8+
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Synonyms
ValueSource
12,13-Epoxy-9,15-octadecadienoateGenerator
Chemical FormulaC18H30O3
Average Mass294.4350 Da
Monoisotopic Mass294.21949 Da
IUPAC Name(9E)-11-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}undec-9-enoic acid
Traditional Name(9E)-11-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}undec-9-enoic acid
CAS Registry NumberNot Available
SMILES
CC\C=C/CC1OC1C\C=C\CCCCCCCC(O)=O
InChI Identifier
InChI=1/C18H30O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h3,8,10-11,16-17H,2,4-7,9,12-15H2,1H3,(H,19,20)/b10-3-,11-8+
InChI KeyBKKGUKSHPCTUGE-GSRSKSEFNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
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
logP5.12ChemAxon
pKa (Strongest Acidic)4.99ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.83 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity88.04 m³·mol⁻¹ChemAxon
Polarizability36.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Toporkova YY, Smirnova EO, Lantsova NV, Mukhtarova LS, Grechkin AN: Detection of the First Epoxyalcohol Synthase/Allene Oxide Synthase (CYP74 Clan) in the Lancelet (Branchiostoma belcheri, Chordata). Int J Mol Sci. 2021 Apr 29;22(9):4737. doi: 10.3390/ijms22094737. [PubMed:33947016  ] 
  2. Toporkova YY, Askarova EK, Gorina SS, Ogorodnikova AV, Mukhtarova LS, Grechkin AN: Epoxyalcohol synthase activity of the CYP74B enzymes of higher plants. Biochim Biophys Acta Mol Cell Biol Lipids. 2020 Sep;1865(9):158743. doi:  10.1016/j.bbalip.2020.158743. Epub 2020 May 25. [PubMed:32464332  ] 
  3. Toporkova YY, Smirnova EO, Gorina SS, Mukhtarova LS, Grechkin AN: Detection of the first higher plant epoxyalcohol synthase: Molecular cloning and characterisation of the CYP74M2 enzyme of spikemoss Selaginella moellendorffii. Phytochemistry. 2018 Dec;156:73-82. doi: 10.1016/j.phytochem.2018.08.010. Epub  2018 Sep 6. [PubMed:30195166  ]