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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-23 01:44:46 UTC

Update Date

2022-03-07 02:49:31 UTC

HMDB ID

HMDB0006353

Secondary Accession Numbers

HMDB06353

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

HMDB0006353
     RDKit          3D
Dolichol phosphate
 49 48  0  0  0  0  0  0  0  0999 V2000
   -4.4328    1.3825   -1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2029    0.3141   -0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6444    0.6871   -0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8170   -0.8835   -0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5867   -1.6214   -0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4241   -0.8825   -0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069   -1.7494   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1672   -2.9264   -1.8686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231   -1.4435   -0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1446   -2.2404   -0.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2509   -1.3642   -0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5290   -0.1720    0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9194   -0.5603    1.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799    0.6874   -0.6325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9288    1.9154    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4256    1.5361    1.3983 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8015    2.9628    2.2585 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.7567    2.7265    3.7310 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2962    3.4950    1.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219    4.1058    1.7993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2817    1.1760   -2.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4484    1.5894   -0.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0153    2.3614   -1.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2323   -0.2084    0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0660    1.2484   -0.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6217    1.3238    0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6338   -1.5317    0.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7922   -2.4504   -1.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3705   -2.2224    0.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5954   -0.3269   -1.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1474   -0.1288   -0.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3841   -2.7537   -2.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1036   -3.1526   -2.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045   -3.8287   -1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957   -0.5811    0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361   -3.0560   -1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794   -2.7727    0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -1.9087   -1.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961   -0.9534   -1.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6173    0.4814    0.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -1.4403    1.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500    0.2518    2.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0038   -0.7319    1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4827    0.0926   -0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0950    1.0789   -1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0194    2.5748    0.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6551    2.5681   -0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6646    2.9349    0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9018    4.3969    0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 17 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 19 48  1  0
 20 49  1  0
M  END


  Mrv1652309121723102D          

 20 19  0  0  0  0            999 V2000
    4.4395   -0.3017    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.6168   -0.3017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2659   -0.3017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4361    0.5211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4361   -1.1278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9037    0.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1907   -0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4775    0.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7646   -0.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4742    0.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0514    0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611   -0.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4775    0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1907   -0.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844    0.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9620    0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6752   -0.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3915    0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1081   -0.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3950    0.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  STY  1   1 SRU
M  SCN  1   1 HT 
M  SAL   1  5  11  12  13  14  15
M  SDI   1  4   -2.5848   -0.4697   -2.5848    0.3360
M  SDI   1  4    0.3189    0.3360    0.3189   -0.4697
M  SBL   1  2  10  15
M  SMT   1 n
M  END
> <DATABASE_ID>
HMDB0006353

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CCOP(O)(O)=O)CC\C=C(/C)CCC=C(C)C

> <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)/b14-9+

> <INCHI_KEY>
DZHSRPJGCZHWOM-NTEUORMPSA-N

> <FORMULA>
(C5H8)nC10H21O4P

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <ALOGPS_LOGP>
3.40

> <ALOGPS_LOGS>
-3.80

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.85e-02 g/l

$$$$

HMDB0006353
     RDKit          3D
Dolichol phosphate
 49 48  0  0  0  0  0  0  0  0999 V2000
   -4.4328    1.3825   -1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2029    0.3141   -0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6444    0.6871   -0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8170   -0.8835   -0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5867   -1.6214   -0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4241   -0.8825   -0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069   -1.7494   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1672   -2.9264   -1.8686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231   -1.4435   -0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1446   -2.2404   -0.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2509   -1.3642   -0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5290   -0.1720    0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9194   -0.5603    1.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799    0.6874   -0.6325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9288    1.9154    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4256    1.5361    1.3983 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8015    2.9628    2.2585 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.7567    2.7265    3.7310 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2962    3.4950    1.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219    4.1058    1.7993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2817    1.1760   -2.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4484    1.5894   -0.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0153    2.3614   -1.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2323   -0.2084    0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0660    1.2484   -0.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6217    1.3238    0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6338   -1.5317    0.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7922   -2.4504   -1.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3705   -2.2224    0.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5954   -0.3269   -1.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1474   -0.1288   -0.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3841   -2.7537   -2.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1036   -3.1526   -2.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045   -3.8287   -1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957   -0.5811    0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361   -3.0560   -1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794   -2.7727    0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -1.9087   -1.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961   -0.9534   -1.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6173    0.4814    0.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -1.4403    1.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500    0.2518    2.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0038   -0.7319    1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4827    0.0926   -0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0950    1.0789   -1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0194    2.5748    0.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6551    2.5681   -0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6646    2.9349    0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9018    4.3969    0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 17 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 19 48  1  0
 20 49  1  0
M  END

HEADER    PROTEIN                                 12-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-17         0                                  
HETATM    1  P   UNK     0       8.287  -0.563   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0       6.751  -0.563   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.830  -0.563   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.281   0.973   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.281  -2.105   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.420   0.198   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.089  -0.557   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.758   0.217   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.427  -0.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.752   1.753   0.000  0.00  0.00           C+0
HETATM   11  C     n     1      -0.096   0.224   0.000  0.00  0.00           C+0
HETATM   12  C     n     1      -1.421  -0.550   0.000  0.00  0.00           C+0
HETATM   13  C     n     1      -2.758   0.224   0.000  0.00  0.00           C+0
HETATM   14  C     n     1      -4.089  -0.550   0.000  0.00  0.00           C+0
HETATM   15  C     n     1      -2.771   1.760   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.529   0.224   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.860  -0.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.197   0.224   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -9.535  -0.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.204   1.760   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8   11                                                       
CONECT   10    8                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13   16                                                       
CONECT   15   13                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0006353
HETATM    1  C1  UNL     1      -4.433   1.383  -1.066  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.203   0.314  -0.443  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.644   0.687  -0.090  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.817  -0.883  -0.164  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.587  -1.621  -0.322  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.424  -0.883  -0.822  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.207  -1.749  -0.981  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.167  -2.926  -1.869  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.123  -1.443  -0.294  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.145  -2.240  -0.378  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.251  -1.364  -0.866  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.529  -0.172   0.024  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.919  -0.560   1.409  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.580   0.687  -0.632  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.929   1.915   0.170  1.00  0.00           C  
HETATM   16  O1  UNL     1       4.426   1.536   1.398  1.00  0.00           O  
HETATM   17  P1  UNL     1       4.801   2.963   2.258  1.00  0.00           P  
HETATM   18  O2  UNL     1       4.757   2.726   3.731  1.00  0.00           O  
HETATM   19  O3  UNL     1       6.296   3.495   1.712  1.00  0.00           O  
HETATM   20  O4  UNL     1       3.622   4.106   1.799  1.00  0.00           O  
HETATM   21  H1  UNL     1      -4.282   1.176  -2.171  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.448   1.589  -0.628  1.00  0.00           H  
HETATM   23  H3  UNL     1      -5.015   2.361  -1.083  1.00  0.00           H  
HETATM   24  H4  UNL     1      -7.232  -0.208   0.134  1.00  0.00           H  
HETATM   25  H5  UNL     1      -7.066   1.248  -0.946  1.00  0.00           H  
HETATM   26  H6  UNL     1      -6.622   1.324   0.803  1.00  0.00           H  
HETATM   27  H7  UNL     1      -5.634  -1.532   0.327  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.792  -2.450  -1.086  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.371  -2.222   0.605  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.595  -0.327  -1.753  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.147  -0.129  -0.027  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.384  -2.754  -2.638  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.104  -3.153  -2.372  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.905  -3.829  -1.245  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.096  -0.581   0.381  1.00  0.00           H  
HETATM   36  H16 UNL     1       1.036  -3.056  -1.150  1.00  0.00           H  
HETATM   37  H17 UNL     1       1.379  -2.773   0.562  1.00  0.00           H  
HETATM   38  H18 UNL     1       3.208  -1.909  -1.003  1.00  0.00           H  
HETATM   39  H19 UNL     1       1.996  -0.953  -1.866  1.00  0.00           H  
HETATM   40  H20 UNL     1       1.617   0.481   0.109  1.00  0.00           H  
HETATM   41  H21 UNL     1       2.334  -1.440   1.763  1.00  0.00           H  
HETATM   42  H22 UNL     1       2.650   0.252   2.115  1.00  0.00           H  
HETATM   43  H23 UNL     1       4.004  -0.732   1.460  1.00  0.00           H  
HETATM   44  H24 UNL     1       4.483   0.093  -0.887  1.00  0.00           H  
HETATM   45  H25 UNL     1       3.095   1.079  -1.576  1.00  0.00           H  
HETATM   46  H26 UNL     1       3.019   2.575   0.288  1.00  0.00           H  
HETATM   47  H27 UNL     1       4.655   2.568  -0.381  1.00  0.00           H  
HETATM   48  H28 UNL     1       6.665   2.935   0.971  1.00  0.00           H  
HETATM   49  H29 UNL     1       3.902   4.397   0.874  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4    4
CONECT    3   24   25   26
CONECT    4    5   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8    9    9
CONECT    8   32   33   34
CONECT    9   10   35
CONECT   10   11   36   37
CONECT   11   12   38   39
CONECT   12   13   14   40
CONECT   13   41   42   43
CONECT   14   15   44   45
CONECT   15   16   46   47
CONECT   16   17
CONECT   17   18   18   19   20
CONECT   19   48
CONECT   20   49
END

HMDB0006353
     RDKit          3D
Dolichol phosphate
 49 48  0  0  0  0  0  0  0  0999 V2000
   -4.4328    1.3825   -1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2029    0.3141   -0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6444    0.6871   -0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8170   -0.8835   -0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5867   -1.6214   -0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4241   -0.8825   -0.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069   -1.7494   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1672   -2.9264   -1.8686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231   -1.4435   -0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1446   -2.2404   -0.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2509   -1.3642   -0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5290   -0.1720    0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9194   -0.5603    1.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799    0.6874   -0.6325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9288    1.9154    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4256    1.5361    1.3983 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8015    2.9628    2.2585 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.7567    2.7265    3.7310 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2962    3.4950    1.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6219    4.1058    1.7993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2817    1.1760   -2.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4484    1.5894   -0.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0153    2.3614   -1.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2323   -0.2084    0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0660    1.2484   -0.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6217    1.3238    0.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6338   -1.5317    0.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7922   -2.4504   -1.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3705   -2.2224    0.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5954   -0.3269   -1.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1474   -0.1288   -0.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3841   -2.7537   -2.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1036   -3.1526   -2.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045   -3.8287   -1.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957   -0.5811    0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361   -3.0560   -1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794   -2.7727    0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082   -1.9087   -1.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961   -0.9534   -1.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6173    0.4814    0.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -1.4403    1.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500    0.2518    2.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0038   -0.7319    1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4827    0.0926   -0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0950    1.0789   -1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0194    2.5748    0.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6551    2.5681   -0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6646    2.9349    0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9018    4.3969    0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 17 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 19 48  1  0
 20 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dolichol phosphoric acid	Generator
Dolichol monophosphate	HMDB
Dolichol-P	HMDB
Dolichol-phosphate	HMDB
Dolichol-PO4	HMDB
Dolichyl-phosphate	HMDB
Dolychol phosphate	HMDB

Chemical Formula

(C₅H₈)nC₁₀H₂₁O₄P

Average Molecular Weight

Not Available

Monoisotopic Molecular Weight

Not Available

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

34457-14-2

SMILES

CC(CCOP(O)(O)=O)CC\C=C(/C)CCC=C(C)C

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)/b14-9+

InChI Key

DZHSRPJGCZHWOM-NTEUORMPSA-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

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.4	ALOGPS
logS	-3.8	ALOGPS
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	167.189	30932474
DeepCCS	[M-H]-	164.831	30932474
DeepCCS	[M-2H]-	197.717	30932474
DeepCCS	[M+Na]+	173.283	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.53 minutes	32390414
Predicted by Siyang on May 30, 2022	12.2124 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.27 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2262.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	240.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	167.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	121.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	567.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	558.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	90.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1052.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	499.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	848.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	394.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	325.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	294.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	345.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.2 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dolichol phosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9630000000-2363aa5efd80171e1ae6	2016-09-22	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichol phosphate 10V, Positive-QTOF	splash10-0a4i-1496000000-ec1df72c4987cf00bd11	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichol phosphate 20V, Positive-QTOF	splash10-0a4i-7950000000-ed6057f6c271c64a2f44	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichol phosphate 40V, Positive-QTOF	splash10-06di-9700000000-4d5d06a74044e737dbcc	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichol phosphate 10V, Negative-QTOF	splash10-0ufr-8009000000-fca69e87dde06919337c	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichol phosphate 20V, Negative-QTOF	splash10-004i-9000000000-03b07e3a8c2213183b79	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichol phosphate 40V, Negative-QTOF	splash10-004i-9000000000-ea573660632a9aabc66c	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichol phosphate 10V, Negative-QTOF	splash10-0ufs-9006000000-8fa91985de106ac27a82	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichol phosphate 20V, Negative-QTOF	splash10-004i-9000000000-c47fda1609169ecd31ba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichol phosphate 40V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichol phosphate 10V, Positive-QTOF	splash10-0a4i-2972000000-fd11c45c9967a687430a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichol phosphate 20V, Positive-QTOF	splash10-0kpi-4910000000-ca81e148de16a194714e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichol phosphate 40V, Positive-QTOF	splash10-00ss-9300000000-1cdfee9a400fec1d5d18	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Endoplasmic reticulum

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023901

KNApSAcK ID

Not Available

Chemspider ID

4444045

KEGG Compound ID

C00110

BioCyc ID

Not Available

BiGG ID

1809214

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280322

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

DOLP_L

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

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. Epub 2007 Jan 31. [PubMed:17273964 ]

Enzymes

Enzyme Details

1. Dolichol-phosphate mannosyltransferase

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Transfers mannose from GDP-mannose to dolichol monophosphate to form dolichol phosphate mannose (Dol-P-Man) which is the mannosyl donor in pathways leading to N-glycosylation, glycosyl phosphatidylinositol membrane anchoring, and O-mannosylation of proteins.
Gene Name:: DPM1
Uniprot ID:: O60762
Molecular weight:: 29633.995

Enzyme Details

2. Protein O-mannosyl-transferase 1

General function:: Involved in mannosyltransferase activity
Specific function:: Transfers mannosyl residues to the hydroxyl group of serine or threonine residues. Coexpression of both POMT1 and POMT2 is necessary for enzyme activity, expression of either POMT1 or POMT2 alone is insufficient.
Gene Name:: POMT1
Uniprot ID:: Q9Y6A1
Molecular weight:: 82566.18

Enzyme Details

3. Protein O-mannosyl-transferase 2

General function:: Involved in mannosyltransferase activity
Specific function:: Transfers mannosyl residues to the hydroxyl group of serine or threonine residues. Coexpression of both POMT1 and POMT2 is necessary for enzyme activity, expression of either POMT1 or POMT2 alone is insufficient.
Gene Name:: POMT2
Uniprot ID:: Q9UKY4
Molecular weight:: 84213.155

Enzyme Details

4. Dolichyl-phosphate beta-glucosyltransferase

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Not Available
Gene Name:: ALG5
Uniprot ID:: Q9Y673
Molecular weight:: 33524.965

Enzyme Details

5. UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferase

General function:: Involved in phospho-N-acetylmuramoyl-pentapeptide-transferase activity
Specific function:: Catalyzes the initial step in the synthesis of dolichol-P-P-oligosaccharides.
Gene Name:: DPAGT1
Uniprot ID:: Q9H3H5
Molecular weight:: 46089.485

Enzyme Details

6. Dolichyldiphosphatase 1

General function:: Involved in catalytic activity
Specific function:: Required for efficient N-glycosylation. Necessary for maintaining optimal levels of dolichol-linked oligosaccharides. Hydrolyzes dolichyl pyrophosphate at a very high rate and dolichyl monophosphate at a much lower rate. Does not act on phosphatidate (By similarity).
Gene Name:: DOLPP1
Uniprot ID:: Q86YN1
Molecular weight:: 22133.63

Showing metabocard for Dolichol phosphate (HMDB0006353)

MOL for HMDB0006353 (Dolichol phosphate)

3D MOL for HMDB0006353 (Dolichol phosphate)

3D SDF for HMDB0006353 (Dolichol phosphate)

3D-SDF for HMDB0006353 (Dolichol phosphate)

PDB for HMDB0006353 (Dolichol phosphate)

3D PDB for HMDB0006353 (Dolichol phosphate)

SMILES for HMDB0006353 (Dolichol phosphate)

INCHI for HMDB0006353 (Dolichol phosphate)

Structure for HMDB0006353 (Dolichol phosphate)

3D Structure for HMDB0006353 (Dolichol phosphate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra

Enzymes