NP-MRD: Showing NP-Card for 3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid (NP0220318)

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Record Information

Version

2.0

Created at

2022-09-05 21:35:33 UTC

Updated at

2022-09-05 21:35:33 UTC

NP-MRD ID

NP0220318

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid

Description

3-(14-Methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. 3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid is found in Burkholderia gladioli. Based on a literature review very few articles have been published on 3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052223352D          

 33 32  0  0  0  0            999 V2000
   -1.5987   16.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132   15.6158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132   14.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0276   14.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0276   13.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7421   13.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7421   12.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4566   11.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4566   11.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1711   10.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1711    9.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8855    9.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8855    8.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6000    8.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3145    8.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6000    7.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3145    6.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3145    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0289    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0289    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7434    4.4783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3145    4.4783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8855    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8855    6.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1711    5.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5987   14.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8842   14.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5987   13.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8842   13.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8842   12.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1698   11.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5987   11.9033    0.0000 C   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  1  0  0  0  0
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  5  6  2  0  0  0  0
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  8  9  1  0  0  0  0
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 11 10  1  4  0  0  0
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 12 13  1  0  0  0  0
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 14 15  1  0  0  0  0
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 16 17  2  0  0  0  0
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 18 23  1  0  0  0  0
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  3 27  1  0  0  0  0
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 27 29  2  0  0  0  0
 29 30  1  4  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
M  END

     RDKit          3D

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   -5.9334    2.3217   -0.7611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1145   -1.6657   -1.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309052223352D          

 33 32  0  0  0  0            999 V2000
   -1.5987   16.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0220318

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(CC=CC=CCCC=CCC(C)C=CC(CC(O)=O)=CC(O)=O)C(C)=CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O5/c1-22(2)16-18-24(4)26(33-5)15-13-11-9-7-6-8-10-12-14-23(3)17-19-25(20-27(29)30)21-28(31)32/h7,9-13,16-20,23,26H,6,8,14-15,21H2,1-5H3,(H,29,30)(H,31,32)

> <INCHI_KEY>
GYDAWNYQSVBMMP-UHFFFAOYSA-N

> <FORMULA>
C28H40O5

> <MOLECULAR_WEIGHT>
456.623

> <EXACT_MASS>
456.287574388

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.708061652881014

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid

> <JCHEM_LOGP>
6.304033565333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.882768449410252

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.151646792074479

> <JCHEM_PKA_STRONGEST_BASIC>
-4.154114270924211

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
142.41020000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.984  29.919   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.318  29.149   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.318  27.609   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.652  26.839   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.652  25.299   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.985  24.529   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.985  22.989   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.319  22.219   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.319  20.679   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.653  19.909   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.653  18.369   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.986  17.599   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.986  16.059   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -12.320  15.289   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -13.654  16.059   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -12.320  13.749   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -13.654  12.979   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -13.654  11.439   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -14.987  10.669   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -14.987   9.129   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -16.321   8.359   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0     -13.654   8.359   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0     -12.320  10.669   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.986  11.439   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -10.986  12.979   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -9.653  10.669   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.984  26.839   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.651  27.609   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.984  25.299   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.651  24.529   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.651  22.989   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.317  22.219   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.984  22.219   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    3   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   64    0
END

View in JSmol

Synonyms

Value	Source
3-(14-Methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioate	Generator

Chemical Formula

C₂₈H₄₀O₅

Average Mass

456.6230 Da

Monoisotopic Mass

456.28757 Da

IUPAC Name

3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid

Traditional Name

3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid

CAS Registry Number

Not Available

SMILES

COC(CC=CC=CCCC=CCC(C)C=CC(CC(O)=O)=CC(O)=O)C(C)=CC=C(C)C

InChI Identifier

InChI=1S/C28H40O5/c1-22(2)16-18-24(4)26(33-5)15-13-11-9-7-6-8-10-12-14-23(3)17-19-25(20-27(29)30)21-28(31)32/h7,9-13,16-20,23,26H,6,8,14-15,21H2,1-5H3,(H,29,30)(H,31,32)

InChI Key

GYDAWNYQSVBMMP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Burkholderia gladioli	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-chain fatty acid
Methyl-branched fatty acid
Branched fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	6.3	ChemAxon
pKa (Strongest Acidic)	4.15	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	142.41 m³·mol⁻¹	ChemAxon
Polarizability	54.71 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162816494

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid (NP0220318)

MOL for NP0220318 (3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid)

3D MOL for NP0220318 (3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid)

3D SDF for NP0220318 (3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid)

3D-SDF for NP0220318 (3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid)

PDB for NP0220318 (3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid)

3D PDB for NP0220318 (3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid)

SMILES for NP0220318 (3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid)

INCHI for NP0220318 (3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid)

Structure for NP0220318 (3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid)

3D Structure for NP0220318 (3-(14-methoxy-3,15,18-trimethylnonadeca-1,5,9,11,15,17-hexaen-1-yl)pent-2-enedioic acid)