NP-MRD: Showing NP-Card for (9e,13e,17e)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid (NP0142092)

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Record Information

Version

2.0

Created at

2022-09-01 20:33:19 UTC

Updated at

2022-09-01 20:33:20 UTC

NP-MRD ID

NP0142092

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9e,13e,17e)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid

Description

CHEMBL450380 belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. (9e,13e,17e)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid is found in Xestospongia muta. Based on a literature review very few articles have been published on CHEMBL450380.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 37  0  0  0  0  0  0  0  0999 V2000
   -4.9039    0.9162   -1.1940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5510    0.8001   -0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8428    1.0766    1.0495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9484    0.3942   -0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1913   -0.9810    0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4472   -2.0874   -0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0140   -1.9149   -0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7959   -1.7985   -0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3963   -1.6561    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1877   -1.5283    0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2520   -1.3793    0.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8927   -0.6888   -0.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3591   -0.5680   -0.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6845    0.9258   -0.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1673    0.9985   -0.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7760    1.5285    0.4958 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2282    1.6018    0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4395    1.6482    0.6044 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8745    1.6913    0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5456    0.7810    1.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4505    0.8581    1.2852 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -5.2876    1.4218    1.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3404    0.5062   -1.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5473    1.1359    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0422   -1.0215    1.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3020   -1.1658    0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7840   -3.0815    0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7317   -2.1865   -1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8298   -1.8342    0.9164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3744   -0.2076   -1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7823   -1.1252    0.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8420   -0.8841   -1.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3012    1.3988   -1.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1860    1.4066    0.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7207    0.5911   -1.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2223    1.9369    1.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4132    2.4865    0.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9722    0.0048    1.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  3  0
  8  9  1  0
  9 10  3  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  3  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 19 37  1  0
 20 38  1  0
M  END


  Mrv1652309012222332D          

 21 20  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9533    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6677    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0967    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8112    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5256    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2401    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9546    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6690    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3835    3.6020    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  3  0  0  0  0
  8  9  1  0  0  0  0
  9 10  3  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  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  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  3  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0142092

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CCCC#CC#C\C=C\CC\C=C\C#C\C=C\Br

> <INCHI_IDENTIFIER>
InChI=1S/C18H17BrO2/c19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(20)21/h1-2,7,9,15,17H,3,5,12,14,16H2,(H,20,21)/b2-1+,9-7+,17-15+

> <INCHI_KEY>
KQTFPHGJDWNEQY-TYHBFTGESA-N

> <FORMULA>
C18H17BrO2

> <MOLECULAR_WEIGHT>
345.236

> <EXACT_MASS>
344.041193

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
36.36630088878992

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9E,13E,17E)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid

> <ALOGPS_LOGP>
5.01

> <JCHEM_LOGP>
5.353914278

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.700914988514332

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
94.2667

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.78e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9E,13E,17E)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-SEP-22         0                                  
HETATM    1  O   UNK     0      -0.357   1.334   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.645   2.874   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.978   3.644   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.312   4.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.646   5.184   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.979   4.414   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.313   5.184   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.647   4.414   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.980   5.184   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.314   4.414   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.648   5.184   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.982   5.954   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.315   6.724   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.649   5.954   0.000  0.00  0.00           C+0
HETATM   21 Br   UNK     0      24.983   6.724   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    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                                                       
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                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₇BrO₂

Average Mass

345.2360 Da

Monoisotopic Mass

344.04119 Da

IUPAC Name

(9E,13E,17E)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid

Traditional Name

(9E,13E,17E)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCCC#CC#C\C=C\CC\C=C\C#C\C=C\Br

InChI Identifier

InChI=1S/C18H17BrO2/c19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(20)21/h1-2,7,9,15,17H,3,5,12,14,16H2,(H,20,21)/b2-1+,9-7+,17-15+

InChI Key

KQTFPHGJDWNEQY-TYHBFTGESA-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 long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Halogenated fatty acid
Straight chain fatty acid
Unsaturated fatty acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Bromoalkene
Vinyl bromide
Vinyl halide
Haloalkene
Organohalogen compound
Organobromide
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
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	5.01	ALOGPS
logP	5.35	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	94.27 m³·mol⁻¹	ChemAxon
Polarizability	36.37 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

8580707

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10405269

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (9e,13e,17e)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid (NP0142092)

MOL for NP0142092 ((9e,13e,17e)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid)

3D MOL for NP0142092 ((9e,13e,17e)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid)

3D SDF for NP0142092 ((9e,13e,17e)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid)

3D-SDF for NP0142092 ((9e,13e,17e)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid)

PDB for NP0142092 ((9e,13e,17e)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid)

3D PDB for NP0142092 ((9e,13e,17e)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid)

SMILES for NP0142092 ((9e,13e,17e)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid)

INCHI for NP0142092 ((9e,13e,17e)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid)

Structure for NP0142092 ((9e,13e,17e)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid)

3D Structure for NP0142092 ((9e,13e,17e)-18-bromooctadeca-9,13,17-trien-5,7,15-triynoic acid)