NP-MRD: Showing NP-Card for α linolenic acid (NP0232593)

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Record Information

Version

1.0

Created at

2022-09-06 13:52:46 UTC

Updated at

2022-09-06 13:52:46 UTC

NP-MRD ID

NP0232593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

α linolenic acid

Description

Alpha-Linolenic acid, also known as a-linolenate, 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 linolenic acid is found in Abutilon ramosum, Agaricus blazei, Agave decipiens, Allamanda cathartica, Amaranthus tricolor, Apios americana, Arnica montana, Asclepias speciosa, Azima tetracantha, Bellis perennis, Bidens pilosa, Brassica napus, Bryonia alba, Camellia sinensis, Canavalia ensiformis, Cannabis sativa, Capparis spinosa, Carica papaya, Catharanthus roseus, Celastrus paniculatus, Centaurea aspera, Chamaecyparis formosensis, Clitoria ternatea, Colletia spinosissima, Consolida regalis, Crotalaria pallida, Croton cortesianus, Cryptomeria japonica, Cucumis melo, Cucumis sativus, Cucurbita foetidissima, Cuphea epilobiifolia, Cystoclonium purpureum, Dictamnus albus, Dipteryx lacunifera, Dunaliella primolecta, Elaeis guineensis, Elymus repens, Erigeron caucasicus, Eriobotrya japonica, Euphausia superba, Euphorbia characias, Euphorbia glareosa, Festuca rubra, Fimbristylis quinquangularis, Garcinia dulcis, Ginkgo biloba, Gleditsia triacanthos, Glehnia littoralis, Glycine max, Gnetum edule, Gossypium hirsutum, Helianthus porteri, Hieracium intybaceum, Hippophae rhamnoides, Hirschfeldia incana, Homo sapiens, Houttuynia cordata, Hoya pottsii, Hyoscyamus muticus, Hypericum perforatum, Isatis tinctoria, Lactarius deliciosus, Lantana ukambensis, Larix gmelinii, Lathraea squamaria, Lepidium meyenii, Lepidium sativum, Ligularia macrophylla, Macrococculus pomiferus, Mangifera indica, Momordica charantia, Monotropa uniflora, Mus musculus, Musa paradisiaca, Nervilia aragoana, Nicotiana tabacum, Nigella sativa, Ocimum basilicum, Olea europaea, Oleandra wallichii, Ononis natrix, Perilla frutescens, Phaseolus coccineus, Picea jezoensis, Picea obovata, Pistacia vera, Pisum sativum, Plagiochila porelloides, Plantago ovata, Pongamia pinnata, Portulaca oleracea, Primula sikkimensis, Prunus mume, Raphanus sativus, Rhodotorula glutinis, Rosa canina, Rosa platyacantha, Rosa taiwanensis, Rosa transmorrisonensis, Salix herbacea, Salmea scandens, Salvia fruticosa, Salvia miltiorrhiza, Salvia trijuga, Schotia brachypetala, Senna alexandrina, Senna siamea, Serenoa repens, Serpocaulon triseriale, Sesamum indicum, Sideritis taurica, Spergula arvensis, Sterculia tragacantha, Stuckenia pectinata, Talaromyces flavus, Taonia atomaria, Taraxacum officinale, Taxus mairei, Thalictrum revolutum, Treculia africana, Trigonella foenum-graecum, Ventilago denticulata, Vigna subterranea and Ziziphus spina-christi. It was first documented in 2002 (PMID: 11913692). Alpha-Linolenic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 20855010) (PMID: 29570652) (PMID: 28219465) (PMID: 16899705).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572004251621392D          

 26 25  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
    0.1401    5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    4.6184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    5.0309    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    3.7934    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    3.3809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    1.3184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21  3  1  0  0  0  0
 22  4  1  0  0  0  0
 23  6  1  0  0  0  0
 24  7  1  0  0  0  0
 25  9  1  0  0  0  0
 26 10  1  0  0  0  0
M  END

     RDKit          3D

 50 49  0  0  0  0  0  0  0  0999 V2000
    8.7228   -0.4115    0.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1819    0.3487   -0.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7784    0.0149   -0.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501    0.9478   -0.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4502    0.5901   -1.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5203    0.8846    0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8063   -0.0704    0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8709    0.1535    1.7579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870   -0.2359    1.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1344   -0.7277    0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2840   -1.0965    0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8766   -0.3296   -1.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2954   -0.7260   -1.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1637   -0.4715   -0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5971   -0.8636   -0.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4417   -0.6098    0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4526    0.8498    1.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9979    1.6731    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2628    2.0083   -0.8836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3207    2.0588    0.1018 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7651   -0.0282    0.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1716   -0.2127    1.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8186   -1.4892    0.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7895    0.0481   -1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2824    1.4292   -0.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5116   -1.0137   -1.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0970    1.9622   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1138    1.2350   -1.9306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3539   -0.4613   -1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4083    1.8937    0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9110   -1.0812    0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1827   -0.4000    2.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8409    1.2292    2.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2716   -0.1095    2.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8919   -0.8539   -0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3384   -2.1883   -0.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8404   -0.9197    0.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2379   -0.5370   -2.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8622    0.7680   -0.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3018   -1.8088   -1.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6950   -0.1438   -2.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7968   -1.1095    0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1369    0.6048    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6393   -1.9353   -0.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9724   -0.2653   -1.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1202   -1.2442    1.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4978   -0.9542    0.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4631    1.2340    1.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0895    0.9987    2.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9848    1.3657    0.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  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
  3 26  1  0
  2 24  1  0
  2 25  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
M  END


  Mrv1572004251621392D          

 26 25  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
    0.1401    5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    4.6184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    5.0309    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    3.7934    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    3.3809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    1.3184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21  3  1  0  0  0  0
 22  4  1  0  0  0  0
 23  6  1  0  0  0  0
 24  7  1  0  0  0  0
 25  9  1  0  0  0  0
 26 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0232593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CC)=C(\[H])C\C([H])=C(/[H])C\C([H])=C(/[H])CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3+,7-6+,10-9+

> <INCHI_KEY>
DTOSIQBPPRVQHS-IUQGRGSQSA-N

> <FORMULA>
C18H30O2

> <MOLECULAR_WEIGHT>
278.436

> <EXACT_MASS>
278.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
34.881051434018424

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9E,12E,15E)-octadeca-9,12,15-trienoic acid

> <ALOGPS_LOGP>
6.62

> <JCHEM_LOGP>
6.059955137666666

> <ALOGPS_LOGS>
-6.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283903808

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
89.63539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.66e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
elaidolinoleic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-16         0                                  
HETATM    1  C   UNK     0       1.595  11.701   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.262  10.931   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.262   9.391   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.072   8.621   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.072   7.081   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.262   6.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.262   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.595   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.929   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0       1.595   8.621   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.406   9.391   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.595   7.081   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.072   4.001   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.929   6.311   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.263   2.461   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9   11   26                                                  
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                                                            
CONECT   21    3                                                            
CONECT   22    4                                                            
CONECT   23    6                                                            
CONECT   24    7                                                            
CONECT   25    9                                                            
CONECT   26   10                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

View in JSmol

Synonyms

Value	Source
a-Linolenate	Generator
a-Linolenic acid	Generator
alpha-Linolenate	Generator
Α-linolenate	Generator
Α-linolenic acid	Generator
Elaidolinolenate	Generator

Chemical Formula

C₁₈H₃₀O₂

Average Mass

278.4360 Da

Monoisotopic Mass

278.22458 Da

IUPAC Name

(9E,12E,15E)-octadeca-9,12,15-trienoic acid

Traditional Name

elaidolinoleic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CC)=C(\[H])C\C([H])=C(/[H])C\C([H])=C(/[H])CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3+,7-6+,10-9+

InChI Key

DTOSIQBPPRVQHS-IUQGRGSQSA-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
Abutilon ramosum	LOTUS Database	35616633
Agaricus blazei	LOTUS Database	35616633
Agave decipiens	LOTUS Database	35616633
Allamanda cathartica	LOTUS Database	35616633
Amaranthus tricolor	LOTUS Database	35616633
Apios americana	LOTUS Database	35616633
Arnica montana	LOTUS Database	35616633
Asclepias speciosa	LOTUS Database	35616633
Azima tetracantha	LOTUS Database	35616633
Bellis perennis	LOTUS Database	35616633
Bidens pilosa	LOTUS Database	35616633
Brassica napus	LOTUS Database	35616633
Bryonia alba	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Canavalia ensiformis	LOTUS Database	35616633
Cannabis sativa	LOTUS Database	35616633
Capparis spinosa	LOTUS Database	35616633
Carica papaya	LOTUS Database	35616633
Catharanthus roseus	LOTUS Database	35616633
Celastrus paniculata	LOTUS Database	35616633
Centaurea aspera	LOTUS Database	35616633
Chamaecyparis formosensis	LOTUS Database	35616633
Clitoria ternatea	LOTUS Database	35616633
Colletia spinosissima	LOTUS Database	35616633
Consolida regalis	LOTUS Database	35616633
Crotalaria pallida	LOTUS Database	35616633
Croton cortesianus	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Cucumis melo	LOTUS Database	35616633
Cucumis sativus	LOTUS Database	35616633
Cucurbita foetidissima	LOTUS Database	35616633
Cuphea epilobiifolia	LOTUS Database	35616633
Cystoclonium purpureum	LOTUS Database	35616633
Dictamnus albus	LOTUS Database	35616633
Dipteryx lacunifera	LOTUS Database	35616633
Dunaliella primolecta	LOTUS Database	35616633
Elaeis guineensis	LOTUS Database	35616633
Elymus repens	LOTUS Database	35616633
Erigeron caucasicus	LOTUS Database	35616633
Eriobotrya japonica	LOTUS Database	35616633
Euphausia superba	LOTUS Database	35616633
Euphorbia characias	LOTUS Database	35616633
Euphorbia glareosa	LOTUS Database	35616633
Festuca rubra	LOTUS Database	35616633
Fimbristylis quinquangularis	LOTUS Database	35616633
Garcinia dulcis	LOTUS Database	35616633
Ginkgo biloba	LOTUS Database	35616633
Gleditsia triacanthos	LOTUS Database	35616633
Glehnia littoralis	LOTUS Database	35616633
Glycine max	LOTUS Database	35616633
Gnetum edule	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Helianthus porteri	LOTUS Database	35616633
Hieracium intybaceum All.	LOTUS Database	35616633
Hippophae rhamnoides	LOTUS Database	35616633
Hirschfeldia incana	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Houttuynia cordata	LOTUS Database	35616633
Hoya pottsii	LOTUS Database	35616633
Hyoscyamus muticus	LOTUS Database	35616633
Hypericum perforatum	LOTUS Database	35616633
Isatis tinctoria	LOTUS Database	35616633
Lactarius deliciosus	LOTUS Database	35616633
Lantana ukambensis	LOTUS Database	35616633
Larix gmelini	LOTUS Database	35616633
Lathraea squamaria	LOTUS Database	35616633
Lepidium meyenii	LOTUS Database	35616633
Lepidium sativum	LOTUS Database	35616633
Ligularia macrophylla	LOTUS Database	35616633
Macrococculus pomiferus	LOTUS Database	35616633
Mangifera indica	LOTUS Database	35616633
Momordica charantia	LOTUS Database	35616633
Monotropa uniflora	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633
Musa paradisiaca	LOTUS Database	35616633
Nervilia aragoana	LOTUS Database	35616633
Nicotiana tabacum	LOTUS Database	35616633
Nigella sativa	LOTUS Database	35616633
Ocimum basilicum	LOTUS Database	35616633
Olea europaea	LOTUS Database	35616633
Oleandra wallichii	LOTUS Database	35616633
Ononis natrix	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Phaseolus coccineus	LOTUS Database	35616633
Picea jezoensis	LOTUS Database	35616633
Picea obovata	LOTUS Database	35616633
Pistacia vera	LOTUS Database	35616633
Pisum sativum	LOTUS Database	35616633
Plagiochila porelloides	LOTUS Database	35616633
Plantago ovata	LOTUS Database	35616633
Pongamia pinnata	LOTUS Database	35616633
Portulaca oleracea	LOTUS Database	35616633
Primula sikkimensis	LOTUS Database	35616633
Prunus mume	LOTUS Database	35616633
Raphanus sativus	LOTUS Database	35616633
Rhodotorula glutinis	LOTUS Database	35616633
Rosa canina	LOTUS Database	35616633
Rosa platyacantha	LOTUS Database	35616633
Rosa taiwanensis	LOTUS Database	35616633
Rosa transmorrisonensis	LOTUS Database	35616633
Salix herbacea	LOTUS Database	35616633
Salmea scandens	LOTUS Database	35616633
Salvia fruticosa	LOTUS Database	35616633
Salvia miltiorrhiza	LOTUS Database	35616633
Salvia trijuga	LOTUS Database	35616633
Schotia brachypetala	LOTUS Database	35616633
Senna alexandrina	LOTUS Database	35616633
Senna siamea	LOTUS Database	35616633
Serenoa repens	LOTUS Database	35616633
Serpocaulon triseriale	LOTUS Database	35616633
Sesamum indicum	LOTUS Database	35616633
Sideritis taurica	LOTUS Database	35616633
Spergula arvensis	LOTUS Database	35616633
Sterculia tragacantha	LOTUS Database	35616633
Stuckenia pectinata	LOTUS Database	35616633
Talaromyces flavus	LOTUS Database	35616633
Taonia atomaria	LOTUS Database	35616633
Taraxacum officinale	LOTUS Database	35616633
Taxus mairei	LOTUS Database	35616633
Thalictrum revolutum	LOTUS Database	35616633
Treculia africana	LOTUS Database	35616633
Trigonella foenum-graecum	LOTUS Database	35616633
Ventilago denticulata	LOTUS Database	35616633
Vigna subterranea	LOTUS Database	35616633
Ziziphus spina-christi	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
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

Unsaturated fatty acids (LMFA01030153 )

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	6.62	ALOGPS
logP	6.06	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.99	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	13	ChemAxon
Refractivity	89.64 m³·mol⁻¹	ChemAxon
Polarizability	34.88 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alpha-Linolenic acid

METLIN ID

Not Available

PubChem Compound

5282822

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026. [PubMed:29570652 ]
van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. [PubMed:16899705 ]
LOTUS database [Link]

Showing NP-Card for α linolenic acid (NP0232593)

MOL for NP0232593 (α linolenic acid)

3D MOL for NP0232593 (α linolenic acid)

3D SDF for NP0232593 (α linolenic acid)

3D-SDF for NP0232593 (α linolenic acid)

PDB for NP0232593 (α linolenic acid)

3D PDB for NP0232593 (α linolenic acid)

SMILES for NP0232593 (α linolenic acid)

INCHI for NP0232593 (α linolenic acid)

Structure for NP0232593 (α linolenic acid)

3D Structure for NP0232593 (α linolenic acid)