MiMeDB: Showing metabocard for Dolichol phosphate (MMDBc0033164)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:37:18 UTC

Update Date

2024-04-30 20:01:56 UTC

Metabolite ID

MMDBc0033164

Metabolite Identification

Common Name

Dolichol phosphate

Description

Dolichol phosphate is the most prevalent polyisoprenyl-glycosyl carrier found in mammals. It is involved in reactions such as the C-4 and O-mannosylation of proteins, the formation of glycosylphosphatidylinositol (GPI) anchors and the N-glycosylation of proteins. The chain length of eukaryotic dolichol molecules differs from 14 to 17 isoprene units in unicellular organisms like yeast whereas mammalian cells produce dolichol with 18-21 isoprene units. During the de novo synthesis of dolichol in eukaryotes, farnesyl pyrophosphate, a metabolite of cholesterol biosynthesis, is elongated by successive condensations to isopentenyl pyrophosphate molecules. These reactions are catalyzed by cis-isopentenyltransferases. After the polyisoprene pyrophosphate chain has reached its final length, both phosphate residues are released by mono- or pyrophosphatases. The isoprene unit of the polyprenol is then reduced by a nicotinamide adenine dinucleotide phosphate (NADPH)-dependent microsomal reductase. The final step in dolichol phosphate synthesis is catalyzed by dolichol kinase (DK1), an enzyme that transfers a phosphate from choline-phosphate cytidine triphosphate (CTP) to dolichol. Once synthesized, dolichol phosphate can react with cytosolic GDP-mannose in the endoplasmic reticulum membrane to form dolichyl phosphate D-mannose. A new inherited metabolic disorder, Dolichol kinase (DK1) deficiency has recently been discovered. Affected patients present with a very severe clinical phenotype, with death in early infancy. Symptoms include secondary microencephaly, dry, thin, parchmentlike skin, hyperkeratosis, minimal hair growth and muscular hypotonia. (PMID: 17273964 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311192105372D          

 49 48  0  0  0  0            999 V2000
   -3.0493    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2079    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5617   -0.0228    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1788   -0.0228    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    1.8642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1528    1.8642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6541   -0.6939    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344    0.1030    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3222    1.8642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5817    1.8642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1632    0.0558    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    1.5395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.8414    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6818   -0.8244    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6250   -0.7431    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8708    0.1712    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1801    1.8642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4396    1.8642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9960    0.0376    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    1.5395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513    1.8414    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9533    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6677    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0802    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822    1.5395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552    1.8414    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9533   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5521   -0.8314    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4902   -0.7369    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270    0.1757    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  4  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 42 45  1  0  0  0  0
 41 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 46 49  1  0  0  0  0
M  END


  Mrv1652311192105372D          

 49 48  0  0  0  0            999 V2000
   -3.0493    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2079    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5617   -0.0228    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1788   -0.0228    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    1.8642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1528    1.8642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6541   -0.6939    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344    0.1030    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3222    1.8642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5817    1.8642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1632    0.0558    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    1.5395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.8414    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6818   -0.8244    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6250   -0.7431    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8708    0.1712    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1801    1.8642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4396    1.8642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9960    0.0376    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    1.5395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513    1.8414    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9533    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6677    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0802    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822    1.5395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552    1.8414    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9533   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5521   -0.8314    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4902   -0.7369    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270    0.1757    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  4  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 42 45  1  0  0  0  0
 41 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 46 49  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033164

> <DATABASE_NAME>
MIME

> <SMILES>
[H]OP(=O)(O[H])OC([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H29O4P/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-19-20(16,17)18/h7,9,15H,5-6,8,10-12H2,1-4H3,(H2,16,17,18)

> <INCHI_KEY>
DZHSRPJGCZHWOM-UHFFFAOYSA-N

> <FORMULA>
C15H29O4P

> <MOLECULAR_WEIGHT>
304.367

> <EXACT_MASS>
304.180346412

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.540860885621555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(3,7,11-trimethyldodeca-6,10-dien-1-yl)oxy]phosphonic acid

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
4.288203561

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.823239539177949

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8000172005152635

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
85.16159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3,7,11-trimethyldodeca-6,10-dien-1-yl)oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-NOV-21         0                                  
HETATM    1  H   UNK     0      -5.692   1.334   0.000  0.00  0.00           H+0
HETATM    2  O   UNK     0      -4.358   0.564   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0      -3.025   1.334   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0      -2.255   0.000   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -3.795   2.667   0.000  0.00  0.00           O+0
HETATM    6  H   UNK     0      -3.025   4.001   0.000  0.00  0.00           H+0
HETATM    7  O   UNK     0      -1.691   2.104   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0      -1.049  -0.043   0.000  0.00  0.00           H+0
HETATM   10  H   UNK     0       0.334  -0.043   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       1.667   3.480   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0       0.285   3.480   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       0.976   0.564   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       2.310  -0.206   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       1.221  -1.295   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       3.080  -1.540   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       3.798   0.192   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       4.335   3.480   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.953   3.480   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       5.905   0.104   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.977   2.874   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       7.081   3.437   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0       7.645   1.334   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.645  -0.206   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0       6.873  -1.539   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       8.633  -1.387   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       9.092   0.320   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0       8.978   2.104   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0       9.670   3.480   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       8.287   3.480   0.000  0.00  0.00           H+0
HETATM   36  C   UNK     0      10.312   1.334   0.000  0.00  0.00           C+0
HETATM   37  H   UNK     0      11.192   0.070   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0      10.312   2.874   0.000  0.00  0.00           H+0
HETATM   39  C   UNK     0      11.646   2.104   0.000  0.00  0.00           C+0
HETATM   40  H   UNK     0      12.416   3.437   0.000  0.00  0.00           H+0
HETATM   41  C   UNK     0      12.979   1.334   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.313   2.104   0.000  0.00  0.00           C+0
HETATM   43  H   UNK     0      15.083   0.770   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0      15.647   2.874   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      13.543   3.437   0.000  0.00  0.00           H+0
HETATM   46  C   UNK     0      12.979  -0.206   0.000  0.00  0.00           C+0
HETATM   47  H   UNK     0      12.231  -1.552   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      13.982  -1.376   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      14.424   0.328   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    7                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5                                                            
CONECT    7    3    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   16   20                                             
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20   14   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
CONECT   33   28   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   46                                                  
CONECT   42   41   43   44   45                                             
CONECT   43   42                                                            
CONECT   44   42                                                            
CONECT   45   42                                                            
CONECT   46   41   47   48   49                                             
CONECT   47   46                                                            
CONECT   48   46                                                            
CONECT   49   46                                                            
MASTER        0    0    0    0    0    0    0    0   49    0   96    0
END

Synonyms

Value	Source
[(3,7,11-Trimethyldodeca-6,10-dien-1-yl)oxy]phosphonate	Generator

Molecular Formula

C₁₅H₂₉O₄P

Average Mass

304.367

Monoisotopic Mass

304.180346412

IUPAC Name

[(3,7,11-trimethyldodeca-6,10-dien-1-yl)oxy]phosphonic acid

Traditional Name

(3,7,11-trimethyldodeca-6,10-dien-1-yl)oxyphosphonic acid

CAS Registry Number

34457-14-2

SMILES

[H]OP(=O)(O[H])OC([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H29O4P/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-19-20(16,17)18/h7,9,15H,5-6,8,10-12H2,1-4H3,(H2,16,17,18)

InChI Key

DZHSRPJGCZHWOM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.048 g/L	ALOGPS
logP	3.4	ALOGPS
logP	4.29	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	1.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	85.16 m³·mol⁻¹	ChemAxon
Polarizability	34.54 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 (TMS_2_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane

Biospecimen Locations

Feces

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000792	Dolichyl diphosphate	Dolichol phosphate	dolichyldiphosphatase 1	VMH	12137737
MMDBr0000796	Dolichyl b-D-glucosyl phosphate	Dolichol phosphate	Not Available	VMH	12137737
MMDBr0000800	Cytidine triphosphate	CDP	Not Available	VMH	30371894
MMDBr0000804	Dolichol phosphate	Dolichol-20	ALG10, alpha-1,2-glucosyltransferase	VMH	30371894
MMDBr0000806	Dolichol phosphate	Dolichyl phosphate D-mannose	ALG12, alpha-1,6-mannosyltransferase	VMH	30371894
MMDBr0000808	Dolichol phosphate	Dolichol phosphate	Not Available	VMH	30371894
MMDBr0001314	Dolichol phosphate	N-acetyl-D-glucosaminyldiphosphodolichol	dolichyl-phosphate (UDP-N-acetylglucosamine) N-acetylglucosaminephosphotransferase 1 (GlcNAc-1-P transferase)	VMH	30371894
MMDBr0002307	Dolichol phosphate	Dolichyl b-D-glucosyl phosphate	ALG5, dolichyl-phosphate beta-glucosyltransferase	VMH	8280060
MMDBr0010571	Dolichyl diphosphate	Dolichol phosphate	dolichyldiphosphatase 1	VMH; KEGG	30371894
MMDBr0010574	Dolichol phosphate	Dolichyl phosphate D-mannose	dolichyl-phosphate mannosyltransferase polypeptide 1, catalytic subunit	VMH; KEGG	30371894
MMDBr0010575	Dolichol phosphate	Dolichyl b-D-glucosyl phosphate	ALG5, dolichyl-phosphate beta-glucosyltransferase	VMH; KEGG	30371894

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
Human Feces	Detected but not Quantified									HMDB

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

388312

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439166

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Kranz C, Jungeblut C, Denecke J, Erlekotte A, Sohlbach C, Debus V, Kehl HG, Harms E, Reith A, Reichel S, Grobe H, Hammersen G, Schwarzer U, Marquardt T: A defect in dolichol phosphate biosynthesis causes a new inherited disorder with death in early infancy. Am J Hum Genet. 2007 Mar;80(3):433-40. doi: 10.1086/512130. Epub 2007 Jan 31. [PubMed:17273964 ]

Showing metabocard for Dolichol phosphate (MMDBc0033164)

MOL for #<Metabolite:0x00007fecf0a98a28>

3D MOL for #<Metabolite:0x00007fecf0a98a28>

3D SDF for #<Metabolite:0x00007fecf0a98a28>

3D-SDF for #<Metabolite:0x00007fecf0a98a28>

PDB for #<Metabolite:0x00007fecf0a98a28>

3D PDB for #<Metabolite:0x00007fecf0a98a28>

SMILES for #<Metabolite:0x00007fecf0a98a28>

INCHI for #<Metabolite:0x00007fecf0a98a28>

Structure for #<Metabolite:0x00007fecf0a98a28>

3D Structure for #<Metabolite:0x00007fecf0a98a28>