NP-MRD: Showing NP-Card for methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate (NP0215358)

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Record Information

Version

1.0

Created at

2022-09-05 14:57:30 UTC

Updated at

2022-09-05 14:57:30 UTC

NP-MRD ID

NP0215358

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate

Description

Methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate 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 14,16-dibromohexadeca-7,13,15-trien-5-ynoate is found in Xestospongia muta. Based on a literature review very few articles have been published on methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 42  0  0  0  0  0  0  0  0999 V2000
    3.7016    4.4689    1.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3433    3.3278    0.7019 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2343    2.2779    0.6357 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3202    2.3318    1.2543 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8796    1.1007   -0.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9729    0.0448   -0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5236   -1.1289   -0.9941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2739   -1.6553   -0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2302   -2.1071   -0.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9960   -2.6562    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0954   -2.5281   -0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0297   -1.8247   -1.5234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9464   -0.6285   -1.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3557   -1.1091   -1.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3309    0.0652   -1.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7114   -0.4290   -0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3568   -0.0095    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5067    1.2024    1.2917 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -6.6888   -0.4698    0.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3748   -0.0905    1.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6905    1.1155    2.7034 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.4515    4.2950    2.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0959    5.3259    1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7784    4.6598    1.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9408    0.6176    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7128    1.3857   -1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9374    0.4424   -0.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0916   -0.2889    0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3350   -1.9106   -0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3346   -0.8190   -2.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9419   -3.1675    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0169   -2.9499    0.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3456   -2.4885   -2.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0206   -1.5450   -1.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8821   -0.0221   -2.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6214   -0.0135   -0.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6832   -1.8501   -1.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4268   -1.5698   -0.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0165    0.8011   -0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3034    0.5470   -2.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1841   -1.1275   -1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1512   -1.1641   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3977   -0.4563    1.5954 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
 10 31  1  0
 11 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
 19 42  1  0
 20 43  1  0
M  END


  Mrv1652309052216572D          

 21 20  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1908    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9052    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3342    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0487    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7631    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4776    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4776    1.4289    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   13.1921    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9065    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6210    2.6664    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
 10  9  1  4  0  0  0
 10 11  2  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
 16 15  1  4  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  4  0  0  0
M  END
> <DATABASE_ID>
NP0215358

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H22Br2O2/c1-21-17(20)13-11-9-7-5-3-2-4-6-8-10-12-16(19)14-15-18/h2-3,12,14-15H,4,6,8-11,13H2,1H3

> <INCHI_KEY>
UWBYQKWMZGTEIS-UHFFFAOYSA-N

> <FORMULA>
C17H22Br2O2

> <MOLECULAR_WEIGHT>
418.169

> <EXACT_MASS>
415.998656

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
39.297590491045554

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate

> <JCHEM_LOGP>
5.842728722666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.024337473468481

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
98.6452

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate

> <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       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.620   2.667   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.954   4.977   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.288   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.622   4.207   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.956   4.977   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.289   4.207   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.623   4.977   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.957   4.207   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.290   4.977   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.624   4.207   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.958   4.977   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.292   4.207   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0      23.292   2.667   0.000  0.00  0.00          Br+0
HETATM   19  C   UNK     0      24.625   4.977   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.959   4.207   0.000  0.00  0.00           C+0
HETATM   21 Br   UNK     0      27.293   4.977   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   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
Methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoic acid	Generator

Chemical Formula

C₁₇H₂₂Br₂O₂

Average Mass

418.1690 Da

Monoisotopic Mass

415.99866 Da

IUPAC Name

methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate

Traditional Name

methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate

CAS Registry Number

Not Available

SMILES

COC(=O)CCCC#CC=CCCCCC=C(Br)C=CBr

InChI Identifier

InChI=1S/C17H22Br2O2/c1-21-17(20)13-11-9-7-5-3-2-4-6-8-10-12-16(19)14-15-18/h2-3,12,14-15H,4,6,8-11,13H2,1H3

InChI Key

UWBYQKWMZGTEIS-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
Xestospongia muta	LOTUS Database	35616633

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
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Vinyl bromide
Vinyl halide
Haloalkene
Bromoalkene
Organooxygen compound
Organobromide
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organohalogen compound
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	5.84	ChemAxon
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	12	ChemAxon
Refractivity	98.65 m³·mol⁻¹	ChemAxon
Polarizability	39.3 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

289609

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

327030

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate (NP0215358)

MOL for NP0215358 (methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate)

3D MOL for NP0215358 (methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate)

3D SDF for NP0215358 (methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate)

3D-SDF for NP0215358 (methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate)

PDB for NP0215358 (methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate)

3D PDB for NP0215358 (methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate)

SMILES for NP0215358 (methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate)

INCHI for NP0215358 (methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate)

Structure for NP0215358 (methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate)

3D Structure for NP0215358 (methyl 14,16-dibromohexadeca-7,13,15-trien-5-ynoate)