NP-MRD: Showing NP-Card for methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate (NP0228065)

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Record Information

Version

2.0

Created at

2022-09-06 07:34:57 UTC

Updated at

2022-09-06 07:34:57 UTC

NP-MRD ID

NP0228065

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate

Description

Methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate 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 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate is found in Xestospongia testudinaria. Methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 44  0  0  0  0  0  0  0  0999 V2000
   -8.1872    0.9768    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8187    0.7024    0.2963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1098   -0.1871   -0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7001   -0.7464   -1.4358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6980   -0.4789   -0.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1757    0.2991    0.9690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7329   -0.0158    1.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0767   -0.8858    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6271   -1.2085    0.6823 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3146   -0.7441    1.9295 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337   -0.6519   -0.4602 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4013   -1.2485   -1.6296 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6178   -0.8619   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2315   -0.2398    0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7426   -0.3954    0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3942    0.2453   -0.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8994    0.0144   -0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6658    0.5928   -1.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5709    1.5205   -1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8863    2.1085    0.6656 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.5904    2.2965   -2.5597 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -8.2616    1.8208   -0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7044    1.1327    0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6666    0.1045   -0.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5544   -1.5636   -0.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0744   -0.1875   -1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2560    1.3774    0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8039    0.0267    1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1739    0.4327    2.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5456   -1.3941   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5814   -2.3257    0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3510   -1.3924    2.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0805    0.4277   -0.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1440   -0.8850   -2.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8983   -1.9331   -0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0470   -0.3168   -1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8910   -0.8014    1.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9360    0.7961    0.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0978    0.1416    1.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0543   -1.4340    0.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1090   -0.2471   -1.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2567    1.3343   -0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1825    0.4651    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0588   -1.0783   -0.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4878    0.2608   -2.3918 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  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 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  2  3
 19 20  1  0
 19 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
  8 30  1  0
  9 31  1  1
 10 32  1  0
 11 33  1  6
 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
M  END


  Mrv1533004251513182D          

 21 20  0  0  0  0            999 V2000
    0.8546    6.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    5.8559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    4.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    3.3809    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
    3.7125    1.3184    0.0000 O   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
    4.4270    3.3809    0.0000 O   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
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0228065

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CCC=CC(O)C(O)CCCCCC=C(Br)Br

> <INCHI_IDENTIFIER>
InChI=1S/C15H24Br2O4/c1-21-15(20)11-7-6-9-13(19)12(18)8-4-2-3-5-10-14(16)17/h6,9-10,12-13,18-19H,2-5,7-8,11H2,1H3

> <INCHI_KEY>
FFPKKWNJQCYPHB-UHFFFAOYSA-N

> <FORMULA>
C15H24Br2O4

> <MOLECULAR_WEIGHT>
428.161

> <EXACT_MASS>
426.004135

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
38.57075516769303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate

> <ALOGPS_LOGP>
3.88

> <JCHEM_LOGP>
3.596149145666665

> <ALOGPS_LOGS>
-4.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.164031965792265

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.670361319090748

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1697030413541647

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
102.28580000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       1.595  11.701   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.929  10.931   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.929   9.391   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.595   8.621   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.263   8.621   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.263   7.081   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.596   6.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.930   2.461   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.264   6.311   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.266   4.771   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.599   4.001   0.000  0.00  0.00           C+0
HETATM   20 Br   UNK     0      18.933   4.771   0.000  0.00  0.00          Br+0
HETATM   21 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   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   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   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
Methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoic acid	Generator

Chemical Formula

C₁₅H₂₄Br₂O₄

Average Mass

428.1610 Da

Monoisotopic Mass

426.00414 Da

IUPAC Name

methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate

Traditional Name

methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate

CAS Registry Number

Not Available

SMILES

COC(=O)CCC=CC(O)C(O)CCCCCC=C(Br)Br

InChI Identifier

InChI=1S/C15H24Br2O4/c1-21-15(20)11-7-6-9-13(19)12(18)8-4-2-3-5-10-14(16)17/h6,9-10,12-13,18-19H,2-5,7-8,11H2,1H3

InChI Key

FFPKKWNJQCYPHB-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 testudinaria	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
1,2-diol
Carboxylic acid ester
Ketene acetal or derivatives
Secondary alcohol
Vinyl halide
Vinyl bromide
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Haloalkene
Bromoalkene
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organobromide
Organohalogen compound
Alcohol
Organic oxide
Hydrocarbon derivative
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	3.88	ALOGPS
logP	3.6	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.67	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	102.29 m³·mol⁻¹	ChemAxon
Polarizability	38.57 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

75599659

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate (NP0228065)

MOL for NP0228065 (methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate)

3D MOL for NP0228065 (methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate)

3D SDF for NP0228065 (methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate)

3D-SDF for NP0228065 (methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate)

PDB for NP0228065 (methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate)

3D PDB for NP0228065 (methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate)

SMILES for NP0228065 (methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate)

INCHI for NP0228065 (methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate)

Structure for NP0228065 (methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate)

3D Structure for NP0228065 (methyl 14,14-dibromo-6,7-dihydroxytetradeca-4,13-dienoate)