NP-MRD: Showing NP-Card for methyl 18,18-dibromooctadec-17-en-5,7-diynoate (NP0288500)

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Record Information

Version

2.0

Created at

2022-09-09 18:13:32 UTC

Updated at

2022-09-09 18:13:32 UTC

NP-MRD ID

NP0288500

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 18,18-dibromooctadec-17-en-5,7-diynoate

Description

Methyl 18,18-dibromo-17-octadecen-5,7-diynoate belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group. Methyl 18,18-dibromo-17-octadecen-5,7-diynoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 49 48  0  0  0  0  0  0  0  0999 V2000
   -9.4200    1.4814    0.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0070    0.4468   -0.4950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2147   -0.6114   -0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8633   -0.6492    1.1343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7667   -1.6981   -0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2391   -1.7737   -0.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7129   -0.3925   -1.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756   -0.2872   -1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0846   -0.1705   -0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6912   -0.0053   -0.7312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5119    0.1494   -0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    0.3586   -0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1896    0.5372    1.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5514    0.7896    1.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6223   -0.2098    1.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0855   -0.6366    0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6186    0.4470   -0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7937    1.1743   -0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9687    0.2717    0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4951   -0.4272   -1.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7473   -0.2628   -1.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4465   -1.1756   -3.0075 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.9627    0.8635   -0.5129 Br  0  0  0  0  0  0  0  0  0  0  0  0
  -10.4258    1.2872    0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4533    2.4164   -0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6867    1.6112    1.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9171   -1.4903   -2.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2145   -2.6719   -0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8403   -2.5540   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0823   -1.9667    0.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2498    0.3753   -0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0168   -0.1908   -2.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2276    1.2302   -0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4522   -0.5275   -0.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5073    1.4058    1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7169   -0.3133    1.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9376    1.8135    1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4162    0.9264    2.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2232   -1.1622    1.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4993    0.0200    2.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4270   -1.3592   -0.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0260   -1.2908    0.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9388    0.0243   -1.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7790    1.1317   -0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5956    1.7517    0.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1271    1.9107   -0.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7501    0.9471    0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7534   -0.4614    0.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8586   -1.0826   -1.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  3  0
  9 10  1  0
 10 11  3  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  3
 21 22  1  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
M  END

  Mrv1533004161507202D          

 23 22  0  0  0  0            999 V2000
   -4.1467    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322    0.4934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177    1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033    0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    2.5559    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    1.3184    0.0000 Br  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  3  0  0  0  0
  9 10  1  0  0  0  0
 10 11  3  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0288500

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CCCC#CC#CCCCCCCCCC=C(Br)Br

> <INCHI_IDENTIFIER>
InChI=1S/C19H26Br2O2/c1-23-19(22)17-15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18(20)21/h16H,2-4,6,8,10,12-15,17H2,1H3

> <INCHI_KEY>
JBWUHDWKJDUVAJ-UHFFFAOYSA-N

> <FORMULA>
C19H26Br2O2

> <MOLECULAR_WEIGHT>
446.223

> <EXACT_MASS>
444.029956

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
43.93852104066379

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 18,18-dibromooctadec-17-en-5,7-diynoate

> <ALOGPS_LOGP>
6.92

> <JCHEM_LOGP>
7.211473465666666

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.024337501462878

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
115.41900000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.82e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 18,18-dibromooctadec-17-en-5,7-diynoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -7.740   1.691   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.407   0.921   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.073   1.691   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.073   3.231   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.739   0.921   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.406   1.691   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.072   0.921   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.262   1.691   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.595   2.461   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.929   3.231   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.266   4.771   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.599   4.001   0.000  0.00  0.00           C+0
HETATM   22 Br   UNK     0      18.933   4.771   0.000  0.00  0.00          Br+0
HETATM   23 Br   UNK     0      17.599   2.461   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    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                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

View in JSmol

Synonyms

Value	Source
Methyl 18,18-dibromo-17-octadecen-5,7-diynoic acid	Generator

Chemical Formula

C₁₉H₂₆Br₂O₂

Average Mass

446.2230 Da

Monoisotopic Mass

444.02996 Da

IUPAC Name

methyl 18,18-dibromooctadec-17-en-5,7-diynoate

Traditional Name

methyl 18,18-dibromooctadec-17-en-5,7-diynoate

CAS Registry Number

Not Available

SMILES

COC(=O)CCCC#CC#CCCCCCCCCC=C(Br)Br

InChI Identifier

InChI=1S/C19H26Br2O2/c1-23-19(22)17-15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18(20)21/h16H,2-4,6,8,10,12-15,17H2,1H3

InChI Key

JBWUHDWKJDUVAJ-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid methyl esters

Alternative Parents

Substituents

Fatty acid methyl ester
Methyl ester
Carboxylic acid ester
Ketene acetal or derivatives
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Vinyl bromide
Vinyl halide
Bromoalkene
Haloalkene
Organobromide
Organohalogen compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Halogenated fatty acids (LMFA01090090 )

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	6.92	ALOGPS
logP	7.21	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	115.42 m³·mol⁻¹	ChemAxon
Polarizability	43.94 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

15518454

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 18,18-dibromooctadec-17-en-5,7-diynoate (NP0288500)

MOL for NP0288500 (methyl 18,18-dibromooctadec-17-en-5,7-diynoate)

3D MOL for NP0288500 (methyl 18,18-dibromooctadec-17-en-5,7-diynoate)

3D SDF for NP0288500 (methyl 18,18-dibromooctadec-17-en-5,7-diynoate)

3D-SDF for NP0288500 (methyl 18,18-dibromooctadec-17-en-5,7-diynoate)

PDB for NP0288500 (methyl 18,18-dibromooctadec-17-en-5,7-diynoate)

3D PDB for NP0288500 (methyl 18,18-dibromooctadec-17-en-5,7-diynoate)

SMILES for NP0288500 (methyl 18,18-dibromooctadec-17-en-5,7-diynoate)

INCHI for NP0288500 (methyl 18,18-dibromooctadec-17-en-5,7-diynoate)

Structure for NP0288500 (methyl 18,18-dibromooctadec-17-en-5,7-diynoate)

3D Structure for NP0288500 (methyl 18,18-dibromooctadec-17-en-5,7-diynoate)