MiMeDB: Showing metabocard for PA(14:0/0:0) (MMDBc0033257)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:41:14 UTC

Update Date

2024-04-30 20:03:24 UTC

Metabolite ID

MMDBc0033257

Metabolite Identification

Common Name

PA(14:0/0:0)

Description

PA(14:0/0:0) is also known as 1-tetradecanoyl-sn-glycero-3-phosphate, 1-myristoyl lysophosphatidic acid or 1-myristoylglycerol 3-phosphate, belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position. 1-tetradecanoyl-sn-glycero-3-phosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0062321
     RDKit          3D
1-tetradecanoyl-sn-glycero-3-phosphate
 60 59  0  0  0  0  0  0  0  0999 V2000
   -8.6794   -1.5072   -2.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4190   -0.2031   -1.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3912   -0.3957   -0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1945    0.9265    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2112    0.9181    1.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8366    0.4992    1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2110    1.3892   -0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8187    0.9371   -0.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8829    0.9404    0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5301    0.4720    0.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4847    0.4416    1.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8345   -0.0251    0.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8030   -0.0376    2.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1603   -0.5057    1.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1172   -0.5910    2.4176 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3053   -0.8276    0.3046 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4633   -1.2597   -0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5359   -0.2167   -0.3267 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9413    0.1799    0.9190 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7444   -0.8312   -1.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7159    0.1502   -1.1404 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0576   -0.4952   -1.9404 P   0  0  0  0  0  5  0  0  0  0  0  0
   11.0370   -0.9630   -0.9017 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6144   -1.7871   -2.9385 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7192    0.7421   -2.8953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0851   -1.5695   -3.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7356   -1.5334   -2.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4569   -2.3863   -1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3707    0.1794   -1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0398    0.5089   -2.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8148   -1.1374    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4791   -0.7684   -0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9365    1.6928   -0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1799    1.2423    0.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2352    1.9473    1.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5628    0.2414    2.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1922    0.5909    1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8432   -0.5544    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8259    1.2549   -0.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1724    2.4246    0.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4287    1.6849   -1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8051   -0.0355   -0.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2009    0.2869    1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7325    1.9801    1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1506    1.1057   -0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5869   -0.5678   -0.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1056   -0.2104    2.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5685    1.4697    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792   -1.0072    0.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2093    0.6988    0.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375   -0.7181    2.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9397    0.9993    2.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2251   -1.5135   -1.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8534   -2.2027    0.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1765    0.6532   -0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9381    1.1542    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4601   -1.1117   -2.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0447   -1.7068   -0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9579   -2.6149   -2.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7796    1.5720   -2.3605 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  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 22 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  6
 19 56  1  0
 20 57  1  0
 20 58  1  0
 24 59  1  0
 25 60  1  0
M  END


  Mrv0541 02241222592D          

 25 24  0  0  1  0            999 V2000
    7.9480    5.4138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9480    6.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3770    5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8059    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5204    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2349    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9493    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6638    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3783    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0927    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2336    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5191    5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8046    5.0013    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.0901    4.5888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3921    5.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2171    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  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  1  0  0  0  0
 13 14  1  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  1  0  0  0  0
  1 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033257

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H35O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(19)23-14-16(18)15-24-25(20,21)22/h16,18H,2-15H2,1H3,(H2,20,21,22)/t16-/m1/s1

> <INCHI_KEY>
FAZBDRGXCKPVJU-MRXNPFEDSA-N

> <FORMULA>
C17H35O7P

> <MOLECULAR_WEIGHT>
382.4294

> <EXACT_MASS>
382.212039986

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
42.90216185472971

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R)-2-hydroxy-3-(tetradecanoyloxy)propoxy]phosphonic acid

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
4.069336518333333

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.531115837556447

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.505317785248875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4039997949880556

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
95.77839999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-myristoyl lpa

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062321
     RDKit          3D
1-tetradecanoyl-sn-glycero-3-phosphate
 60 59  0  0  0  0  0  0  0  0999 V2000
   -8.6794   -1.5072   -2.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4190   -0.2031   -1.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3912   -0.3957   -0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1945    0.9265    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2112    0.9181    1.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8366    0.4992    1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2110    1.3892   -0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8187    0.9371   -0.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8829    0.9404    0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5301    0.4720    0.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4847    0.4416    1.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8345   -0.0251    0.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8030   -0.0376    2.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1603   -0.5057    1.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1172   -0.5910    2.4176 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3053   -0.8276    0.3046 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4633   -1.2597   -0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5359   -0.2167   -0.3267 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9413    0.1799    0.9190 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7444   -0.8312   -1.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7159    0.1502   -1.1404 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0576   -0.4952   -1.9404 P   0  0  0  0  0  5  0  0  0  0  0  0
   11.0370   -0.9630   -0.9017 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6144   -1.7871   -2.9385 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7192    0.7421   -2.8953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0851   -1.5695   -3.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7356   -1.5334   -2.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4569   -2.3863   -1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3707    0.1794   -1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0398    0.5089   -2.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8148   -1.1374    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4791   -0.7684   -0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9365    1.6928   -0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1799    1.2423    0.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2352    1.9473    1.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5628    0.2414    2.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1922    0.5909    1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8432   -0.5544    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8259    1.2549   -0.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1724    2.4246    0.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4287    1.6849   -1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8051   -0.0355   -0.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2009    0.2869    1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7325    1.9801    1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1506    1.1057   -0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5869   -0.5678   -0.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1056   -0.2104    2.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5685    1.4697    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792   -1.0072    0.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2093    0.6988    0.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375   -0.7181    2.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9397    0.9993    2.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2251   -1.5135   -1.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8534   -2.2027    0.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1765    0.6532   -0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9381    1.1542    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4601   -1.1117   -2.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0447   -1.7068   -0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9579   -2.6149   -2.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7796    1.5720   -2.3605 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  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 22 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  6
 19 56  1  0
 20 57  1  0
 20 58  1  0
 24 59  1  0
 25 60  1  0
M  END

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      14.836  10.106   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      14.836  11.646   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      16.170   9.336   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      17.504  10.106   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      18.837   9.336   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      18.837   7.796   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      20.171  10.106   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.505   9.336   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.838  10.106   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.172   9.336   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.506  10.106   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.839   9.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.173  10.106   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.507   9.336   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.841  10.106   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.174   9.336   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.508  10.106   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      34.842   9.336   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      36.175  10.106   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.503   9.336   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.169  10.106   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0      10.835   9.336   0.000  0.00  0.00           P+0
HETATM   23  O   UNK     0       9.502   8.566   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.065  10.669   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      11.605   8.002   0.000  0.00  0.00           O+0
CONECT    1    2    3   20                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    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                                                            
CONECT   20    1   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    HMDB0062321
HETATM    1  C1  UNL     1      -8.679  -1.507  -2.199  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.419  -0.203  -1.475  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.391  -0.396  -0.359  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.195   0.926   0.298  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.211   0.918   1.422  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.837   0.499   1.039  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.211   1.389  -0.010  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.819   0.937  -0.376  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.883   0.940   0.807  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.530   0.472   0.316  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.485   0.442   1.441  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.834  -0.025   0.954  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.803  -0.038   2.105  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.160  -0.506   1.620  1.00  0.00           C  
HETATM   15  O1  UNL     1       5.117  -0.591   2.418  1.00  0.00           O  
HETATM   16  O2  UNL     1       4.305  -0.828   0.305  1.00  0.00           O  
HETATM   17  C15 UNL     1       5.463  -1.260  -0.313  1.00  0.00           C  
HETATM   18  C16 UNL     1       6.536  -0.217  -0.327  1.00  0.00           C  
HETATM   19  O3  UNL     1       6.941   0.180   0.919  1.00  0.00           O  
HETATM   20  C17 UNL     1       7.744  -0.831  -1.059  1.00  0.00           C  
HETATM   21  O4  UNL     1       8.716   0.150  -1.140  1.00  0.00           O  
HETATM   22  P1  UNL     1      10.058  -0.495  -1.940  1.00  0.00           P  
HETATM   23  O5  UNL     1      11.037  -0.963  -0.902  1.00  0.00           O  
HETATM   24  O6  UNL     1       9.614  -1.787  -2.938  1.00  0.00           O  
HETATM   25  O7  UNL     1      10.719   0.742  -2.895  1.00  0.00           O  
HETATM   26  H1  UNL     1      -8.085  -1.570  -3.157  1.00  0.00           H  
HETATM   27  H2  UNL     1      -9.736  -1.533  -2.501  1.00  0.00           H  
HETATM   28  H3  UNL     1      -8.457  -2.386  -1.551  1.00  0.00           H  
HETATM   29  H4  UNL     1      -9.371   0.179  -1.081  1.00  0.00           H  
HETATM   30  H5  UNL     1      -8.040   0.509  -2.240  1.00  0.00           H  
HETATM   31  H6  UNL     1      -7.815  -1.137   0.348  1.00  0.00           H  
HETATM   32  H7  UNL     1      -6.479  -0.768  -0.848  1.00  0.00           H  
HETATM   33  H8  UNL     1      -6.936   1.693  -0.457  1.00  0.00           H  
HETATM   34  H9  UNL     1      -8.180   1.242   0.722  1.00  0.00           H  
HETATM   35  H10 UNL     1      -6.235   1.947   1.880  1.00  0.00           H  
HETATM   36  H11 UNL     1      -6.563   0.241   2.228  1.00  0.00           H  
HETATM   37  H12 UNL     1      -4.192   0.591   1.948  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.843  -0.554   0.764  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.826   1.255  -0.942  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.172   2.425   0.336  1.00  0.00           H  
HETATM   41  H16 UNL     1      -2.429   1.685  -1.109  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.805  -0.035  -0.875  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.201   0.287   1.618  1.00  0.00           H  
HETATM   44  H19 UNL     1      -1.733   1.980   1.184  1.00  0.00           H  
HETATM   45  H20 UNL     1      -0.151   1.106  -0.516  1.00  0.00           H  
HETATM   46  H21 UNL     1      -0.587  -0.568  -0.089  1.00  0.00           H  
HETATM   47  H22 UNL     1       0.106  -0.210   2.242  1.00  0.00           H  
HETATM   48  H23 UNL     1       0.569   1.470   1.829  1.00  0.00           H  
HETATM   49  H24 UNL     1       1.779  -1.007   0.467  1.00  0.00           H  
HETATM   50  H25 UNL     1       2.209   0.699   0.192  1.00  0.00           H  
HETATM   51  H26 UNL     1       2.438  -0.718   2.890  1.00  0.00           H  
HETATM   52  H27 UNL     1       2.940   0.999   2.483  1.00  0.00           H  
HETATM   53  H28 UNL     1       5.225  -1.513  -1.395  1.00  0.00           H  
HETATM   54  H29 UNL     1       5.853  -2.203   0.157  1.00  0.00           H  
HETATM   55  H30 UNL     1       6.176   0.653  -0.942  1.00  0.00           H  
HETATM   56  H31 UNL     1       6.938   1.154   1.015  1.00  0.00           H  
HETATM   57  H32 UNL     1       7.460  -1.112  -2.092  1.00  0.00           H  
HETATM   58  H33 UNL     1       8.045  -1.707  -0.472  1.00  0.00           H  
HETATM   59  H34 UNL     1       9.958  -2.615  -2.557  1.00  0.00           H  
HETATM   60  H35 UNL     1      10.780   1.572  -2.360  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7   37   38
CONECT    7    8   39   40
CONECT    8    9   41   42
CONECT    9   10   43   44
CONECT   10   11   45   46
CONECT   11   12   47   48
CONECT   12   13   49   50
CONECT   13   14   51   52
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   18   53   54
CONECT   18   19   20   55
CONECT   19   56
CONECT   20   21   57   58
CONECT   21   22
CONECT   22   23   23   24   25
CONECT   24   59
CONECT   25   60
END

HMDB0062321
     RDKit          3D
1-tetradecanoyl-sn-glycero-3-phosphate
 60 59  0  0  0  0  0  0  0  0999 V2000
   -8.6794   -1.5072   -2.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4190   -0.2031   -1.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3912   -0.3957   -0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1945    0.9265    0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2112    0.9181    1.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8366    0.4992    1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2110    1.3892   -0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8187    0.9371   -0.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8829    0.9404    0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5301    0.4720    0.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4847    0.4416    1.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8345   -0.0251    0.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8030   -0.0376    2.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1603   -0.5057    1.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1172   -0.5910    2.4176 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3053   -0.8276    0.3046 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4633   -1.2597   -0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5359   -0.2167   -0.3267 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9413    0.1799    0.9190 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7444   -0.8312   -1.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7159    0.1502   -1.1404 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0576   -0.4952   -1.9404 P   0  0  0  0  0  5  0  0  0  0  0  0
   11.0370   -0.9630   -0.9017 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6144   -1.7871   -2.9385 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7192    0.7421   -2.8953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0851   -1.5695   -3.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7356   -1.5334   -2.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4569   -2.3863   -1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3707    0.1794   -1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0398    0.5089   -2.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8148   -1.1374    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4791   -0.7684   -0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9365    1.6928   -0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1799    1.2423    0.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2352    1.9473    1.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5628    0.2414    2.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1922    0.5909    1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8432   -0.5544    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8259    1.2549   -0.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1724    2.4246    0.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4287    1.6849   -1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8051   -0.0355   -0.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2009    0.2869    1.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7325    1.9801    1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1506    1.1057   -0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5869   -0.5678   -0.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1056   -0.2104    2.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5685    1.4697    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792   -1.0072    0.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2093    0.6988    0.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375   -0.7181    2.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9397    0.9993    2.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2251   -1.5135   -1.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8534   -2.2027    0.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1765    0.6532   -0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9381    1.1542    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4601   -1.1117   -2.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0447   -1.7068   -0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9579   -2.6149   -2.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7796    1.5720   -2.3605 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  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 22 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 13 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  6
 19 56  1  0
 20 57  1  0
 20 58  1  0
 24 59  1  0
 25 60  1  0
M  END

Synonyms

Value	Source
(2R)-2-Hydroxy-3-(phosphonooxy)propyl myristate	ChEBI
1-Myristoyl lpa	ChEBI
1-Myristoyl lysophosphatidic acid	ChEBI
1-Myristoyl-2-lyso-sn-glycerol 3-phosphatidic acid	ChEBI
1-Myristoylglycerol 3-phosphate	ChEBI
1-O-Myristoyl-sn-glycerol 3-phosphate	ChEBI
1-O-Tetradecanoyl-sn-glycerol 3-phosphate	ChEBI
1-Tetradecanoyl-sn-glycerol 3-phosphate	ChEBI
1-Tetradecanoylglycerol 3-phosphate	ChEBI
Myristoyl lysophosphatidic acid	ChEBI
PA(14:0/0:0)	ChEBI
(2R)-2-Hydroxy-3-(phosphonooxy)propyl myristic acid	Generator
1-Myristoyl lysophosphatidate	Generator
1-Myristoyl-2-lyso-sn-glycerol 3-phosphatidate	Generator
1-Myristoylglycerol 3-phosphoric acid	Generator
1-O-Myristoyl-sn-glycerol 3-phosphoric acid	Generator
1-O-Tetradecanoyl-sn-glycerol 3-phosphoric acid	Generator
1-Tetradecanoyl-sn-glycerol 3-phosphoric acid	Generator
1-Tetradecanoylglycerol 3-phosphoric acid	Generator
Myristoyl lysophosphatidate	Generator
1-Tetradecanoyl-sn-glycero-3-phosphoric acid	Generator

Molecular Formula

C₁₇H₃₅O₇P

Average Mass

382.4294

Monoisotopic Mass

382.212039986

IUPAC Name

[(2R)-2-hydroxy-3-(tetradecanoyloxy)propoxy]phosphonic acid

Traditional Name

1-myristoyl lpa

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(O)=O

InChI Identifier

InChI=1S/C17H35O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(19)23-14-16(18)15-24-25(20,21)22/h16,18H,2-15H2,1H3,(H2,20,21,22)/t16-/m1/s1

InChI Key

FAZBDRGXCKPVJU-MRXNPFEDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1-acylglycerol-3-phosphates

Alternative Parents

Substituents

1-acylglycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-acyl-sn-glycerol 3-phosphate (CHEBI:62833 )
Monoacylglycerophosphates (LMGP10050007 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	3.11	ALOGPS
logP	4.07	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	95.78 m³·mol⁻¹	ChemAxon
Polarizability	42.9 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-01r2-9430000000-f861d93c20ee8e406d56	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-0cf40b8b7adbde49f580	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0009000000-0cf40b8b7adbde49f580	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ugi-2956000000-1e1f2694e15d344f7ffa	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0009000000-5d141a336820399612f5	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0009000000-5d141a336820399612f5	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02mi-0957000000-bb4d7a4c6e719d94ea81	2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0062321

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7826123

KEGG Compound ID

Not Available

BioCyc ID

CPD0-2254

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9547180

PDB ID

NKN

ChEBI ID

62833

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Moritz A, De Graan PN, Gispen WH, Wirtz KW: Phosphatidic acid is a specific activator of phosphatidylinositol-4-phosphate kinase. J Biol Chem. 1992 Apr 15;267(11):7207-10. [PubMed:1313792 ]
Moolenaar WH, Kruijer W, Tilly BC, Verlaan I, Bierman AJ, de Laat SW: Growth factor-like action of phosphatidic acid. Nature. 1986 Sep 11-17;323(6084):171-3. doi: 10.1038/323171a0. [PubMed:3748188 ]
Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. doi: 10.1016/0092-8674(95)90409-3. [PubMed:7834746 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Yang CY, Frohman MA: Mitochondria: signaling with phosphatidic acid. Int J Biochem Cell Biol. 2012 Aug;44(8):1346-50. doi: 10.1016/j.biocel.2012.05.006. Epub 2012 May 15. [PubMed:22609101 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.

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