NP-MRD: Showing NP-Card for α-kamlolenic acid (NP0206984)

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Record Information

Version

2.0

Created at

2022-09-05 03:25:30 UTC

Updated at

2022-09-05 03:25:30 UTC

NP-MRD ID

NP0206984

Secondary Accession Numbers

None

Natural Product Identification

Common Name

α-kamlolenic acid

Description

Alpha-kamlolenic acid, also known as a-kamlolenate, 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. α-kamlolenic acid is found in Mallotus discolor. α-kamlolenic acid was first documented in 2019 (PMID: 31321646). Based on a literature review very few articles have been published on Alpha-kamlolenic acid (PMID: 32534261).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 51 50  0  0  0  0  0  0  0  0999 V2000
   -8.1187    1.0151    1.0618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9142   -0.1887    1.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6347   -0.6684    2.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0074   -1.0967    0.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2495   -0.4455   -0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3708    0.6544    0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6138    1.3008   -1.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7286    0.3585   -1.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6737   -0.2842   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7225    0.7110   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0538    1.4758   -1.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2345    1.5200   -1.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1680    0.7837   -0.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4741    0.8695   -1.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4566    0.1408   -0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7347    0.2591   -0.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7615   -0.4740    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6932    0.5302    0.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7341   -0.1577    1.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5913   -1.1106    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5429   -1.7051    1.8098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1476   -1.2460    3.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2824   -1.5338    1.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6097   -1.9675    0.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9899   -0.0599   -1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6295   -1.2108   -1.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9689    1.4452    0.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6533    0.2482    0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3835    1.6726   -1.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0440    2.1349   -0.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2336    0.9323   -2.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2989   -0.4541   -2.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1746   -0.9293   -0.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0504   -0.9197   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0307    0.1220    0.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2849    1.3590    0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6713    2.0788   -2.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6123    2.1513   -2.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8471    0.1799    0.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7572    1.4997   -1.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1128   -0.4727    0.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182    0.8901   -1.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2499   -1.0110    1.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3372   -1.1655   -0.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1261    1.2229    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0859    1.1568    1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4228    0.5525    2.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2221   -0.7167    2.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0135   -1.9215    0.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1836   -0.5855    0.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1613   -1.8110    2.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 21 51  1  0
 20 49  1  0
 20 50  1  0
 19 47  1  0
 19 48  1  0
 18 45  1  0
 18 46  1  0
 17 43  1  0
 17 44  1  0
 16 42  1  0
 15 41  1  0
 14 40  1  0
 13 39  1  0
 12 38  1  0
 11 37  1  0
 10 35  1  0
 10 36  1  0
  9 33  1  0
  9 34  1  0
  8 31  1  0
  8 32  1  0
  7 29  1  0
  7 30  1  0
  6 27  1  0
  6 28  1  0
  5 25  1  0
  5 26  1  0
  4 23  1  0
  4 24  1  0
  3 22  1  0
M  END

  Mrv1652309052205252D          

 21 20  0  0  0  0            999 V2000
    2.2836   -2.1434    0.0000 O   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
    2.9980   -3.3809    0.0000 O   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
    4.4270   -2.5559    0.0000 C   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
    9.4283   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427   -0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427   -0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    2.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    2.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    3.6316    0.0000 O   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  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  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0206984

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCCC\C=C\C=C\C=C/CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O3/c19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(20)21/h1-3,5,7,9,19H,4,6,8,10-17H2,(H,20,21)/b2-1-,5-3+,9-7+

> <INCHI_KEY>
YPHQMIRXEFDOQM-ALXQIFAGSA-N

> <FORMULA>
C18H30O3

> <MOLECULAR_WEIGHT>
294.435

> <EXACT_MASS>
294.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.900472380793815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z,11E,13E)-18-hydroxyoctadeca-9,11,13-trienoic acid

> <JCHEM_LOGP>
4.623276521

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.91865246176324

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167332885704

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9595814622066543

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
91.5641

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
α-kamlolenic 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  O   UNK     0       4.263  -4.001   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.596  -4.771   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.596  -6.311   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.930  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.264  -4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.597  -4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.931  -4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.265  -4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.598  -4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.932  -4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.266  -4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.599  -4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.599  -2.461   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.933  -1.691   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.933  -0.151   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.267   0.619   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.267   2.159   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.600   2.929   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.600   4.469   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.934   5.239   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      22.934   6.779   0.000  0.00  0.00           O+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

Value	Source
a-Kamlolenate	Generator
a-Kamlolenic acid	Generator
alpha-Kamlolenate	Generator
Α-kamlolenate	Generator
Α-kamlolenic acid	Generator

Chemical Formula

C₁₈H₃₀O₃

Average Mass

294.4350 Da

Monoisotopic Mass

294.21949 Da

IUPAC Name

(9Z,11E,13E)-18-hydroxyoctadeca-9,11,13-trienoic acid

Traditional Name

α-kamlolenic acid

CAS Registry Number

Not Available

SMILES

OCCCC\C=C\C=C\C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H30O3/c19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(20)21/h1-3,5,7,9,19H,4,6,8,10-17H2,(H,20,21)/b2-1-,5-3+,9-7+

InChI Key

YPHQMIRXEFDOQM-ALXQIFAGSA-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
Mallotus discolor	LOTUS Database	35616633

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
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Other Octadecanoids (LMFA02000156 )

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	4.62	ChemAxon
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	91.56 m³·mol⁻¹	ChemAxon
Polarizability	36.9 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

4446076

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282949

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zeng B, Su M, Chen Q, Chang Q, Wang W, Li H: Anoectochilus roxburghii polysaccharide prevents carbon tetrachloride-induced liver injury in mice by metabolomic analysis. J Chromatogr B Analyt Technol Biomed Life Sci. 2020 Sep 1;1152:122202. doi: 10.1016/j.jchromb.2020.122202. Epub 2020 Jun 2. [PubMed:32534261 ]
Qi S, Xu Y, Luo R, Li P, Huang Z, Huang S, Nie T, Zhang Q, Li Q: Novel Biochemical Insights in the Cerebrospinal Fluid of Patients with Neurosyphilis Based on a Metabonomics Study. J Mol Neurosci. 2019 Sep;69(1):39-48. doi: 10.1007/s12031-019-01320-0. Epub 2019 Jul 18. [PubMed:31321646 ]
LOTUS database [Link]

Showing NP-Card for α-kamlolenic acid (NP0206984)

MOL for NP0206984 (α-kamlolenic acid)

3D MOL for NP0206984 (α-kamlolenic acid)

3D SDF for NP0206984 (α-kamlolenic acid)

3D-SDF for NP0206984 (α-kamlolenic acid)

PDB for NP0206984 (α-kamlolenic acid)

3D PDB for NP0206984 (α-kamlolenic acid)

SMILES for NP0206984 (α-kamlolenic acid)

INCHI for NP0206984 (α-kamlolenic acid)

Structure for NP0206984 (α-kamlolenic acid)

3D Structure for NP0206984 (α-kamlolenic acid)