NP-MRD: Showing NP-Card for 1-linoleoyl-sn-glycerol (NP0212920)

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Record Information

Version

2.0

Created at

2022-09-05 11:44:06 UTC

Updated at

2022-09-05 11:44:07 UTC

NP-MRD ID

NP0212920

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-linoleoyl-sn-glycerol

Description

MG(18:2(9Z,12Z)/0:0/0:0), Also known as (S)-1-monolinolein or a-monoacylglycerol, 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. MG(18:2(9Z,12Z)/0:0/0:0) Is an extremely weak basic (essentially neutral) compound (based on its pKa). 1-linoleoyl-sn-glycerol is found in Streptomyces piomogenus. A 1-acyl-sn-glycerol that is the S-enantiomer of 1-monolinolein.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241201452D          

 26 25  0  0  1  0            999 V2000
   23.4628   -4.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7878   -5.3513    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.1126   -4.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1380   -5.3513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4375   -5.3513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3308   -5.9211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3055   -5.9508    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5769   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2914   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0059   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7203   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4348   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1493   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8638   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5783   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2927   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0072   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7217   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4361   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1507   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8651   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5796   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2941   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0085   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7230   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7230   -4.1137    0.0000 O   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  1  1  0  0  0  0
  5  3  1  0  0  0  0
  2  6  1  6  0  0  0
  2  7  1  1  0  0  0
  9  8  1  0  0  0  0
 10  9  1  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  2  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  2  0  0  0  0
  5 25  1  0  0  0  0
M  END

     RDKit          3D

 63 62  0  0  0  0  0  0  0  0999 V2000
    9.1451    0.7529    0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0153    1.6863    1.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8312    1.4056    0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4248   -0.0289    0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -0.4007   -0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9107   -1.7831   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7717   -2.1658    0.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6702   -1.2627    0.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5131   -1.6744   -0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9101   -0.9145   -0.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3171    0.4348   -1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2657    1.4744   -1.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3477    1.6768    0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1697    0.5523    0.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3528    0.2463   -0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2395    1.4313   -0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3919    1.1755   -1.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2647    0.1042   -0.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1068   -0.4595    0.4436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3627   -0.3532   -1.4068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2345   -1.3528   -0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9657   -0.9805    0.2725 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.6985    0.1887   -0.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9484   -2.0531    0.7068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6118   -1.5779    1.8363 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1074    1.2485    1.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1029   -0.1890    1.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1950    0.6008   -0.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6868    1.5079    2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3394    2.7307    1.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9652    2.0381    0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0811    1.5057   -0.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0883   -0.1725    1.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2287   -0.7332    0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6174   -0.3465   -1.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4626    0.3541   -0.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7435   -2.5032   -0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6169   -3.2411    0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570   -1.5276    1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8905   -0.2120    0.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1540   -2.7115    0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0275   -1.3381   -1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2188    0.7851   -0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6467    0.5587   -2.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    1.2708   -1.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6265    2.4774   -1.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4916    1.8467    0.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9298    2.6424    0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5937   -0.3585    0.9080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6189    0.8456    1.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9636   -0.1207   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9039   -0.5951    0.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7145    2.3380   -0.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6611    1.6343    0.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0771    0.9498   -2.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0227    2.1134   -1.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6472   -2.2997   -0.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9216   -1.5813   -1.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2599   -0.7260    1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1013    0.8416   -0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6982   -2.1697   -0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3826   -2.9666    0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8313   -0.6192    1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
 22 59  1  1
 23 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 21 57  1  0
 21 58  1  0
 17 55  1  0
 17 56  1  0
 16 53  1  0
 16 54  1  0
 15 51  1  0
 15 52  1  0
 14 49  1  0
 14 50  1  0
 13 47  1  0
 13 48  1  0
 12 45  1  0
 12 46  1  0
 11 43  1  0
 11 44  1  0
 10 42  1  0
  9 41  1  0
  8 39  1  0
  8 40  1  0
  7 38  1  0
  6 37  1  0
  5 35  1  0
  5 36  1  0
  4 33  1  0
  4 34  1  0
  3 31  1  0
  3 32  1  0
  2 29  1  0
  2 30  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
M  END


  Mrv0541 02241201452D          

 26 25  0  0  1  0            999 V2000
   23.4628   -4.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7878   -5.3513    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.1126   -4.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1380   -5.3513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4375   -5.3513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3308   -5.9211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3055   -5.9508    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5769   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2914   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0059   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7203   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4348   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1493   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8638   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5783   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2927   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0072   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7217   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4361   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1507   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8651   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5796   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2941   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0085   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7230   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7230   -4.1137    0.0000 O   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  1  1  0  0  0  0
  5  3  1  0  0  0  0
  2  6  1  6  0  0  0
  2  7  1  1  0  0  0
  9  8  1  0  0  0  0
 10  9  1  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  2  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  2  0  0  0  0
  5 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0212920

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](O)(CO)COC(=O)CCCCCCC\C=C/C\C=C/CCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C21H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h6-7,9-10,20,22-23H,2-5,8,11-19H2,1H3/b7-6-,10-9-/t20-/m0/s1

> <INCHI_KEY>
WECGLUPZRHILCT-GSNKCQISSA-N

> <FORMULA>
C21H38O4

> <MOLECULAR_WEIGHT>
354.524

> <EXACT_MASS>
354.277009704

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
43.42712570606009

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2,3-dihydroxypropyl (9Z,12Z)-octadeca-9,12-dienoate

> <ALOGPS_LOGP>
5.56

> <JCHEM_LOGP>
5.247333896333334

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.561713304317518

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.619245765321082

> <JCHEM_PKA_STRONGEST_BASIC>
-2.968684336972288

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
105.54269999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2,3-dihydroxypropyl (9Z,12Z)-octadeca-9,12-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      43.797  -9.261   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      42.537  -9.989   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      41.277  -9.261   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      45.058  -9.989   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      40.017  -9.989   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      41.684 -11.053   0.000  0.00  0.00           O+0
HETATM    7  H   UNK     0      43.504 -11.108   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0      16.010  -9.989   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.344  -9.219   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.678  -9.989   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.011  -9.219   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.345  -9.989   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.679  -9.219   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.012  -9.219   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.346  -9.989   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.680  -9.219   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.013  -9.219   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.347  -9.989   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.681  -9.219   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      32.015  -9.989   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      33.348  -9.219   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      34.682  -9.989   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      36.016  -9.219   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      37.349  -9.989   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      38.683  -9.219   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      38.683  -7.679   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    3    6    7                                             
CONECT    3    2    5                                                       
CONECT    4    1                                                            
CONECT    5    3   25                                                       
CONECT    6    2                                                            
CONECT    7    2                                                            
CONECT    8    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   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26    5                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

View in JSmol

Synonyms

Value	Source
(S)-1-Monolinolein	ChEBI
(S)-1-O-Linoleoylglycerol	ChEBI
1-(9Z,12Z)-Octadecadienoyl-sn-glycerol	ChEBI
1-(9Z,12Z-Octadecadienoyl)-sn-glycerol	ChEBI
1-Linoleoyl-sn-monoglyceride	ChEBI
MG (18:2(N-6)/0:0/0:0)	ChEBI
sn-1-Monolinoleoylglycerol	ChEBI
1-(9Z,12Z-Octadecadienoyl)-rac-glycerol	HMDB
1-LG	HMDB
1-Linoleoyl-glycerol	HMDB
1-Monoacylglyceride	HMDB
1-Monoacylglycerol	HMDB
a-Monoacylglycerol	HMDB
alpha-Monoacylglycerol	HMDB
MAG(18:2)	HMDB
MAG(18:2/0:0)	HMDB
MAG(18:2n6/0:0)	HMDB
MAG(18:2W6/0:0)	HMDB
MG(18:2)	HMDB
MG(18:2/0:0)	HMDB
MG(18:2n6/0:0)	HMDB
MG(18:2W6/0:0)	HMDB
1-Monolinoleoyl-rac-glycerol	HMDB
Glyceryl linoleic acid monoester	HMDB
MLG CPD	HMDB
Monolinolein	HMDB
(9Z,12Z)-2,3-Dihydroxypropyl octadecadienoate	HMDB
(±)-2,3-dihydroxypropyl 9(Z),12(Z)-octadecadienoate	HMDB
1-Glyceryl linoleate	HMDB
1-Linoleylglycerol	HMDB
1-Monolinolein	HMDB
1-O-(9Z,12Z-Octadecadienoyl)glycerol	HMDB
2,3-Dihydroxypropyl linoleate	HMDB
3-O-(9Z,12Z-Octadecadienoyl)glycerol	HMDB
Glycerol 1-monolinolate	HMDB
alpha-Glyceryl linoleate	HMDB
alpha-Monolinolein	HMDB
Α-glyceryl linoleate	HMDB
Α-monolinolein	HMDB

Chemical Formula

C₂₁H₃₈O₄

Average Mass

354.5240 Da

Monoisotopic Mass

354.27701 Da

IUPAC Name

(2S)-2,3-dihydroxypropyl (9Z,12Z)-octadeca-9,12-dienoate

Traditional Name

(2S)-2,3-dihydroxypropyl (9Z,12Z)-octadeca-9,12-dienoate

CAS Registry Number

Not Available

SMILES

[H][C@](O)(CO)COC(=O)CCCCCCC\C=C/C\C=C/CCCCC

InChI Identifier

InChI=1S/C21H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h6-7,9-10,20,22-23H,2-5,8,11-19H2,1H3/b7-6-,10-9-/t20-/m0/s1

InChI Key

WECGLUPZRHILCT-GSNKCQISSA-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
Streptomyces piomogenus	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
1-acyl-sn-glycerol
Monoradylglycerol
Monoacylglycerol
Fatty acid ester
Glycerolipid
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-acyl-sn-glycerol (CHEBI:75561 )
1-monolinolein (CHEBI:75561 )

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	5.56	ALOGPS
logP	5.25	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	105.54 m³·mol⁻¹	ChemAxon
Polarizability	43.43 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

HMDB0011568

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028281

KNApSAcK ID

Not Available

Chemspider ID

4941255

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6436630

PDB ID

Not Available

ChEBI ID

75561

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-linoleoyl-sn-glycerol (NP0212920)

MOL for NP0212920 (1-linoleoyl-sn-glycerol)

3D MOL for NP0212920 (1-linoleoyl-sn-glycerol)

3D SDF for NP0212920 (1-linoleoyl-sn-glycerol)

3D-SDF for NP0212920 (1-linoleoyl-sn-glycerol)

PDB for NP0212920 (1-linoleoyl-sn-glycerol)

3D PDB for NP0212920 (1-linoleoyl-sn-glycerol)

SMILES for NP0212920 (1-linoleoyl-sn-glycerol)

INCHI for NP0212920 (1-linoleoyl-sn-glycerol)

Structure for NP0212920 (1-linoleoyl-sn-glycerol)

3D Structure for NP0212920 (1-linoleoyl-sn-glycerol)