MiMeDB: Showing metabocard for PGP(12:0(3-OH)/15:0cyclo) (MMDBc0032354)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 02:12:58 UTC

Update Date

2022-08-31 18:41:01 UTC

Metabolite ID

MMDBc0032354

Metabolite Identification

Common Name

PGP(12:0(3-OH)/15:0cyclo)

Description

PGP(12:0(3-OH)/15:0cyclo) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PGP(12:0(3-OH)/15:0cyclo), in particular, consists of one 3-hydroxydodecanoyl chain to the C-1 atom, and one cis-9,10-Methylenetetradecanoic acid to the C-2 atom. In E. coli, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase.

Structure

MOL SDF PDB SMILES InChI


  Mrv1572012091519182D          

 51 51  0  0  1  0            999 V2000
    2.7850    0.9634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3818    0.3608    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0919    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8022    0.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9714   -0.3494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7924   -0.3494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6715    0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9613    0.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7968    0.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071   -0.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174    0.3437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9276   -0.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0493    0.6481    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125    0.0209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0493    1.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8811    0.9262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6379    0.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4301    0.5557    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.4301    1.3759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0201   -0.1546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5123    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5123    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2264    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9405    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9405    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6546    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3688    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0830    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7971    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5112    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2254    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9395    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6536    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3678    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5362   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5362   -1.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2504   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9645   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6787   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3928   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1069   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8211   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5352   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2493   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9635   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6776   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3918   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1059   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8200   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5341   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  2  5  1  1  0  0  0
  6  2  1  0  0  0  0
  7  2  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  1  1  1  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  2  0  0  0  0
 11 16  1  6  0  0  0
 17 12  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 18  1  0  0  0  0
 22  4  1  0  0  0  0
 23 22  2  0  0  0  0
 24 22  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 25  1  0  0  0  0
 28 27  1  0  0  0  0
 29 28  1  0  0  0  0
 30 29  1  0  0  0  0
 31 30  1  0  0  0  0
 32 31  1  0  0  0  0
 33 32  1  0  0  0  0
 34 33  1  0  0  0  0
 35 34  1  0  0  0  0
 36  6  1  0  0  0  0
 37 36  2  0  0  0  0
 38 36  1  0  0  0  0
 39 38  1  0  0  0  0
 40 39  1  0  0  0  0
 41 40  1  0  0  0  0
 42 41  1  0  0  0  0
 43 42  1  0  0  0  0
 44 43  1  0  0  0  0
 45 44  1  0  0  0  0
 46 45  1  0  0  0  0
 47 45  1  0  0  0  0
 47 46  1  0  0  0  0
 48 47  1  0  0  0  0
 49 48  1  0  0  0  0
 50 49  1  0  0  0  0
 51 50  1  0  0  0  0
M  END


  Mrv1572012091519182D          

 51 51  0  0  1  0            999 V2000
    2.7850    0.9634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3818    0.3608    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0919    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8022    0.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9714   -0.3494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7924   -0.3494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6715    0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9613    0.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7968    0.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071   -0.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174    0.3437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9276   -0.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0493    0.6481    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125    0.0209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0493    1.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8811    0.9262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6379    0.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4301    0.5557    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.4301    1.3759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0201   -0.1546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5123    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5123    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2264    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9405    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9405    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6546    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3688    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0830    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7971    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5112    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2254    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9395    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6536    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3678    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5362   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5362   -1.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2504   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9645   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6787   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3928   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1069   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8211   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5352   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2493   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9635   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6776   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3918   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1059   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8200   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5341   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  2  5  1  1  0  0  0
  6  2  1  0  0  0  0
  7  2  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  1  1  1  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  2  0  0  0  0
 11 16  1  6  0  0  0
 17 12  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 18  1  0  0  0  0
 22  4  1  0  0  0  0
 23 22  2  0  0  0  0
 24 22  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 25  1  0  0  0  0
 28 27  1  0  0  0  0
 29 28  1  0  0  0  0
 30 29  1  0  0  0  0
 31 30  1  0  0  0  0
 32 31  1  0  0  0  0
 33 32  1  0  0  0  0
 34 33  1  0  0  0  0
 35 34  1  0  0  0  0
 36  6  1  0  0  0  0
 37 36  2  0  0  0  0
 38 36  1  0  0  0  0
 39 38  1  0  0  0  0
 40 39  1  0  0  0  0
 41 40  1  0  0  0  0
 42 41  1  0  0  0  0
 43 42  1  0  0  0  0
 44 43  1  0  0  0  0
 45 44  1  0  0  0  0
 46 45  1  0  0  0  0
 47 45  1  0  0  0  0
 47 46  1  0  0  0  0
 48 47  1  0  0  0  0
 49 48  1  0  0  0  0
 50 49  1  0  0  0  0
 51 50  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032354

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CCCCCCCC1CC1CCCC

> <INCHI_IDENTIFIER>
InChI=1S/C33H64O14P2/c1-3-5-7-8-9-12-15-19-29(34)22-33(37)43-25-31(26-46-49(41,42)45-24-30(35)23-44-48(38,39)40)47-32(36)20-16-13-10-11-14-18-28-21-27(28)17-6-4-2/h27-31,34-35H,3-26H2,1-2H3,(H,41,42)(H2,38,39,40)/t27?,28?,29?,30-,31-/m1/s1

> <INCHI_KEY>
QNDQBDRULUOORK-FOMSTSDASA-N

> <FORMULA>
C33H64O14P2

> <MOLECULAR_WEIGHT>
746.809

> <EXACT_MASS>
746.377130737

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
113

> <JCHEM_AVERAGE_POLARIZABILITY>
81.33735589794881

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-3-({[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

> <ALOGPS_LOGP>
4.18

> <JCHEM_LOGP>
6.581006056000001

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.040206143675361

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3548792963261795

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7987515577175683

> <JCHEM_POLAR_SURFACE_AREA>
215.57999999999996

> <JCHEM_REFRACTIVITY>
182.7853

> <JCHEM_ROTATABLE_BOND_COUNT>
35

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-{[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxydodecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-DEC-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-DEC-15         0                                  
HETATM    1  H   UNK     0       5.199   1.798   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -4.446   0.673   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.772   1.437   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -7.097   0.673   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0      -3.680  -0.652   0.000  0.00  0.00           H+0
HETATM    6  O   UNK     0      -5.213  -0.652   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.120   1.439   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.794   0.673   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.487   0.642   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.813  -0.124   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.139   0.642   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.465  -0.124   0.000  0.00  0.00           C+0
HETATM   13  P   UNK     0       0.092   1.210   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0      -0.583   0.039   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.092   2.606   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.511   1.729   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.791   0.641   0.000  0.00  0.00           O+0
HETATM   18  P   UNK     0       8.270   1.037   0.000  0.00  0.00           P+0
HETATM   19  O   UNK     0       8.270   2.568   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.748   0.641   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       7.504  -0.289   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.423   1.437   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -8.423   2.877   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -9.756   0.665   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -11.089   1.437   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0     -11.089   2.877   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0     -12.422   0.665   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -13.755   1.437   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -15.088   0.665   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -16.421   1.437   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -17.754   0.665   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -19.087   1.437   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -20.420   0.665   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -21.753   1.437   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -23.087   0.665   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.601  -1.436   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.601  -2.876   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -7.934  -0.665   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -9.267  -1.436   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -10.600  -0.665   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -11.933  -1.436   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -13.266  -0.665   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -14.599  -1.436   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -15.932  -0.665   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -17.265  -1.436   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -18.599  -0.665   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -19.931  -1.436   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -21.265  -0.665   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -22.598  -1.436   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -23.931  -0.665   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -25.264  -1.436   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2    3    5    6    7                                             
CONECT    3    2    4                                                       
CONECT    4    3   22                                                       
CONECT    5    2                                                            
CONECT    6    2   36                                                       
CONECT    7    2    8                                                       
CONECT    8    7   13                                                       
CONECT    9   10   13                                                       
CONECT   10    9   11                                                       
CONECT   11    1   10   12   16                                             
CONECT   12   11   17                                                       
CONECT   13    8    9   14   15                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22    4   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36    6   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45   47                                                       
CONECT   47   45   46   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  102    0
END

Synonyms

Not Available

Molecular Formula

C₃₃H₆₄O₁₄P₂

Average Mass

746.809

Monoisotopic Mass

746.377130737

IUPAC Name

[(2R)-3-({[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

Traditional Name

(2R)-3-{[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxydodecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CCCCCCCC1CC1CCCC

InChI Identifier

InChI=1S/C33H64O14P2/c1-3-5-7-8-9-12-15-19-29(34)22-33(37)43-25-31(26-46-49(41,42)45-24-30(35)23-44-48(38,39)40)47-32(36)20-16-13-10-11-14-18-28-21-27(28)17-6-4-2/h27-31,34-35H,3-26H2,1-2H3,(H,41,42)(H2,38,39,40)/t27?,28?,29?,30-,31-/m1/s1

InChI Key

QNDQBDRULUOORK-FOMSTSDASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoglycerophosphates

Direct Parent

Phosphatidylglycerophosphates

Alternative Parents

Substituents

Diacylglycerophosphoglycerophosphate
Sn-glycerol-3-phosphate
Beta-hydroxy acid
Fatty acid ester
Dialkyl phosphate
Monoalkyl phosphate
Dicarboxylic acid or derivatives
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Hydroxy acid
Organic phosphoric acid derivative
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0037 g/L	ALOGPS
logP	4.18	ALOGPS
logP	6.58	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	1.35	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	215.58 Å²	ChemAxon
Rotatable Bond Count	35	ChemAxon
Refractivity	182.79 m³·mol⁻¹	ChemAxon
Polarizability	81.34 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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 (TMS_2_7) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05bb-1870352900-38910cbd16d75f39c3eb	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ac1-3950141300-df76b2711b0acd33a421	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-7940402100-563fcf50ae6ab3d3d97a	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-5790050400-0cc5840c9a0c8044fc4f	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-9230000000-9b8f1e01dbaca6bb8db4	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9010000000-7c363d0fdca65cb4961e	2019-02-23	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	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
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Yurtsever D. (2007). Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A. M.sc. Thesis. Villanova University: U.S.A.

Showing metabocard for PGP(12:0(3-OH)/15:0cyclo) (MMDBc0032354)

MOL for #<Metabolite:0x00007fecdce56070>

3D MOL for #<Metabolite:0x00007fecdce56070>

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3D Structure for #<Metabolite:0x00007fecdce56070>