NP-MRD: Showing NP-Card for (5e,15z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid (NP0294344)

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Record Information

Version

2.0

Created at

2022-09-10 02:50:28 UTC

Updated at

2022-09-10 02:50:29 UTC

NP-MRD ID

NP0294344

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5e,15z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid

Description

6-Bromo-(5E,15Z)-octadeca-5,15-diene-11,13,17-triynoic acid methyl ester 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. (5e,15z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid is found in Leptogium saturninum. Based on a literature review very few articles have been published on 6-bromo-(5E,15Z)-octadeca-5,15-diene-11,13,17-triynoic acid methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 39  0  0  0  0  0  0  0  0999 V2000
   -7.9217    1.3065    0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8724    1.1037   -0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8283    0.8784   -1.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7393    0.3401   -2.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5911   -0.0369   -1.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6312   -0.3699   -1.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4904   -0.7766   -0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5191   -1.1379    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3469   -1.5986    1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1416   -1.3380    0.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0260    0.1006   -0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352    1.0243    1.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3514    1.0229    1.9258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0598    2.0262    3.6251 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.5132    0.4499    1.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1215   -0.3661    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4523    0.3202    0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0947   -0.5171   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3702    0.1184   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7611    1.1906   -0.5691 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0921   -0.5250   -2.1141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9796    1.4898    1.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6764    1.1542   -2.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7198    0.1784   -3.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2320   -1.1068    2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4047   -2.6940    1.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223   -1.7168    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2397   -1.9514   -0.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7697    0.2330   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9436    0.4221   -0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    0.8285    1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0106    2.1006    0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1703    0.5969    2.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4538   -1.3354    1.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5630   -0.5545   -0.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1608    0.3333    1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2692    1.3550    0.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4203   -0.5125   -1.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2725   -1.5280   -0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1087   -0.5080   -2.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 19  1  0
 19 20  2  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  3  0
  7  6  1  0
  6  5  3  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  3  0
 21 40  1  0
 18 38  1  0
 18 39  1  0
 17 36  1  0
 17 37  1  0
 16 34  1  0
 16 35  1  0
 15 33  1  0
 12 31  1  0
 12 32  1  0
 11 29  1  0
 11 30  1  0
 10 27  1  0
 10 28  1  0
  9 25  1  0
  9 26  1  0
  4 24  1  0
  3 23  1  0
  1 22  1  0
M  END


  Mrv1652309102204502D          

 21 20  0  0  0  0            999 V2000
   -0.1914    7.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    7.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    8.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    7.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    6.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    6.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  3  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  1  0  0  0  0
 10 11  1  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
 13 15  2  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  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0294344

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CCC\C=C(\Br)CCCCC#CC#C\C=C/C#C

> <INCHI_IDENTIFIER>
InChI=1S/C18H19BrO2/c1-2-3-4-5-6-7-8-9-10-11-14-17(19)15-12-13-16-18(20)21/h1,3-4,15H,9-14,16H2,(H,20,21)/b4-3-,17-15+

> <INCHI_KEY>
IQBQVQQXKHQANW-BNXREGJKSA-N

> <FORMULA>
C18H19BrO2

> <MOLECULAR_WEIGHT>
347.252

> <EXACT_MASS>
346.056843

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
35.0897721339649

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E,15Z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid

> <JCHEM_LOGP>
5.029698948

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.854708040500722

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
93.39139999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5E,15Z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.357  13.654   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.691  14.424   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.025  15.194   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.358  14.424   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.358  12.884   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.358  11.344   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.358   9.804   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.358   8.264   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.358   6.724   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.025   5.954   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.025   4.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.691   3.644   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.691   2.104   0.000  0.00  0.00           C+0
HETATM   14 Br   UNK     0      -3.025   1.334   0.000  0.00  0.00          Br+0
HETATM   15  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
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   15                                                  
CONECT   14   13                                                            
CONECT   15   13   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
6-Bromo-(5E,15Z)-octadeca-5,15-diene-11,13,17-triynoate methyl ester	Generator

Chemical Formula

C₁₈H₁₉BrO₂

Average Mass

347.2520 Da

Monoisotopic Mass

346.05684 Da

IUPAC Name

(5E,15Z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid

Traditional Name

(5E,15Z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCC\C=C(\Br)CCCCC#CC#C\C=C/C#C

InChI Identifier

InChI=1S/C18H19BrO2/c1-2-3-4-5-6-7-8-9-10-11-14-17(19)15-12-13-16-18(20)21/h1,3-4,15H,9-14,16H2,(H,20,21)/b4-3-,17-15+

InChI Key

IQBQVQQXKHQANW-BNXREGJKSA-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
Leptogium saturninum	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
Unsaturated fatty acid
Carboxylic acid derivative
Carboxylic acid
Acetylide
Monocarboxylic acid or derivatives
Vinyl bromide
Vinyl halide
Haloalkene
Bromoalkene
Organobromide
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Organohalogen compound
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	5.03	ChemAxon
pKa (Strongest Acidic)	3.85	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	93.39 m³·mol⁻¹	ChemAxon
Polarizability	35.09 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

78434792

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129861905

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5e,15z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid (NP0294344)

MOL for NP0294344 ((5e,15z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid)

3D MOL for NP0294344 ((5e,15z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid)

3D SDF for NP0294344 ((5e,15z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid)

3D-SDF for NP0294344 ((5e,15z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid)

PDB for NP0294344 ((5e,15z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid)

3D PDB for NP0294344 ((5e,15z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid)

SMILES for NP0294344 ((5e,15z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid)

INCHI for NP0294344 ((5e,15z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid)

Structure for NP0294344 ((5e,15z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid)

3D Structure for NP0294344 ((5e,15z)-6-bromooctadeca-5,15-dien-11,13,17-triynoic acid)