NP-MRD: Showing NP-Card for laballenic acid (NP0208755)

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Record Information

Version

2.0

Created at

2022-09-05 05:52:55 UTC

Updated at

2022-09-05 05:52:55 UTC

NP-MRD ID

NP0208755

Secondary Accession Numbers

None

Natural Product Identification

Common Name

laballenic acid

Description

Laballenic acid, also known as 18:2 Or laballensaeure, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. laballenic acid was first documented in 2015 (PMID: 26535039). Based on a literature review a small amount of articles have been published on laballenic acid (PMID: 30985104) (PMID: 28777980) (PMID: 32376015).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 52 51  0  0  0  0  0  0  0  0999 V2000
   -7.8147    1.1610   -1.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3883    1.1709   -1.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2385    0.0144   -0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8521   -0.0457    0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7946   -0.2338   -0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3959   -0.2877   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825   -1.4205    0.8610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9090   -1.4996    1.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1051   -1.6992    0.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848   -1.8221    0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8142   -0.5551    1.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428    0.5668    0.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7695    0.7113   -0.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8753    0.8226   -0.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9335    1.6294   -0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2701    1.4880   -0.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7495    0.0421   -0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0667   -0.0831   -1.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6016   -1.2102   -1.4557 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6468    1.0404   -1.9284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4116    2.0067   -1.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7890    1.3694   -2.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3259    0.2058   -1.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1866    2.1128   -0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6813    1.0730   -2.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4544   -0.9520   -0.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9410    0.1612    0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8522   -0.8951    1.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6964    0.8769    0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8155    0.6466   -1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9913   -1.1170   -1.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7147   -0.4045   -0.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2217    0.6933    0.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325   -2.3652    0.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9995   -1.3341    1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6784   -0.5747    2.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8812   -2.3848    2.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1219   -2.5874   -0.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022   -0.7992   -0.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5834   -2.7095    1.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1849   -1.9457    0.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1996   -0.4512    2.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8933   -0.6390    2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9903    1.2892    0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8629    0.3117   -1.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0087    1.2877    0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6179    2.6741   -0.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9994    2.0836   -0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2088    1.8812   -1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9802   -0.5591   -1.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8106   -0.3378    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3687    1.5931   -1.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 20  1  0
 18 19  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 20 52  1  0
M  END

  Mrv1652309052207522D          

 20 19  0  0  0  0            999 V2000
    3.5211    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092    2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6671    2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3815    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6671    1.6204    0.0000 O   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  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  1  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  2  0  0  0  0
 13 14  2  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
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0208755

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC=C=CCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12,14H,2-11,15-17H2,1H3,(H,19,20)

> <INCHI_KEY>
YXJXBVWHSBEPDQ-UHFFFAOYSA-N

> <FORMULA>
C18H32O2

> <MOLECULAR_WEIGHT>
280.452

> <EXACT_MASS>
280.24023027

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.97345279424613

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
octadeca-5,6-dienoic acid

> <JCHEM_LOGP>
6.576151783333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.636177073601133

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
87.08289999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
laballenic acid

> <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       6.573   5.335   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.243   6.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.577   5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.910   4.565   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.244   5.335   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.578   4.565   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.912   5.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.245   4.565   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      30.579   5.335   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      29.245   3.025   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                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
18:2	ChEBI
5,6-Octadecadienoic acid	ChEBI
Laballensaeure	ChEBI
5,6-Octadecadienoate	Generator
Laballenate	Generator

Chemical Formula

C₁₈H₃₂O₂

Average Mass

280.4520 Da

Monoisotopic Mass

280.24023 Da

IUPAC Name

octadeca-5,6-dienoic acid

Traditional Name

laballenic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC=C=CCCCC(O)=O

InChI Identifier

InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12,14H,2-11,15-17H2,1H3,(H,19,20)

InChI Key

YXJXBVWHSBEPDQ-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 lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

octadecadienoic acid (CHEBI:24993 )
allenic fatty acid (CHEBI:24993 )
Unsaturated fatty acids (LMFA01030320 )

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	6.58	ChemAxon
pKa (Strongest Acidic)	4.64	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	14	ChemAxon
Refractivity	87.08 m³·mol⁻¹	ChemAxon
Polarizability	35.97 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

4471896

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5312471

PDB ID

Not Available

ChEBI ID

24993

Good Scents ID

Not Available

References

General References

Huang X, Ma S: Allenation of Terminal Alkynes with Aldehydes and Ketones. Acc Chem Res. 2019 May 21;52(5):1301-1312. doi: 10.1021/acs.accounts.9b00023. Epub 2019 Apr 15. [PubMed:30985104 ]
Choudhary AK, Sunojkumar P, Mishra G: Fatty acid profiling and multivariate analysis in the genus Leucas reveals its nutritional, pharmaceutical and chemotaxonomic significance. Phytochemistry. 2017 Nov;143:72-80. doi: 10.1016/j.phytochem.2017.07.007. Epub 2017 Aug 1. [PubMed:28777980 ]
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LOTUS database [Link]

Showing NP-Card for laballenic acid (NP0208755)

MOL for NP0208755 (laballenic acid)

3D MOL for NP0208755 (laballenic acid)

3D SDF for NP0208755 (laballenic acid)

3D-SDF for NP0208755 (laballenic acid)

PDB for NP0208755 (laballenic acid)

3D PDB for NP0208755 (laballenic acid)

SMILES for NP0208755 (laballenic acid)

INCHI for NP0208755 (laballenic acid)

Structure for NP0208755 (laballenic acid)

3D Structure for NP0208755 (laballenic acid)