Showing Compound Dolichol-14 (FDB023634)

Record Information

Version

1.0

Creation date

2011-09-21 00:32:43 UTC

Update date

2018-05-28 18:36:49 UTC

Primary ID

FDB023634

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Dolichol-14

Description

Dolichols are polyisoprenic molecule ubiquitously present in the lipid fraction of animal and plant tissues, discovered 40 years ago during experiments on the biosynthesis of ubiquinone. The molecular structure of dolichol comprises a sequence of unsaturated isoprenic units bearing a primary terminal hydroxyl group. The length of dolichyl chains depends on the species of the organism from which they are isolated. Mammalian dolichol generally is made up of 16 to 23 unsaturated isoprene units, and the terminal hydroxyl group may exist either free or esterified with fatty acids, phosphoric acid, and pyrophosphoric acid. In biological membranes, this linear polyisoprenoid compound may be located between the two leaflets of the lipid bilayer, close to the free end of the phospholipid fatty acid molecules. Metabolism and function of dolichol were largely unknown until recently. Synthesis of dolichol by the mevalonate pathway was demonstrated in vitro and in vivo in many tissues. The isoprenoid pyrophosphate intermediates are shared by the cholesterol, dolichol, and ubiquinone pathways, and treatment with drugs that block hydroxymethyl glutaryl coenzyme A reductase may significantly decrease their plasma and tissue levels. In humans, there is no apparent positive correlation between serum dolichol and tissue dolichol and age. In view of the total content of the body, half-life of the total body dolichol, and dolichol content in the extracellular space, it was concluded that the dolichol in tissues probably derives from biosynthesis in those tissues and that relocation of dolichol via circulation cannot be prominent in vivo. The levels of dolichol in human serum have apparently no correlation to age or serum total cholesterol, and exhibit a linear correlation to high-density lipoprotein cholesterols which may reflect the fact that the dolichols are associated with the high-density lipoprotein fraction. No enzymic pathways for dolichol degradation were described, but no case of dolichol-storage disease was reported. Shrinkage of tissue because of increased lysosomal degradation in the process of atrophy does not affect the dolichol content and concentration increases. Small quantities of dolichol that may be excreted into the urine at least in part is derived from the lysosomes of the excretory organ, and serum dolichol levels may be elevated in chronic cholestatic liver diseases. Recent evidence shows that phagocytosis may cause the degradation and disposal of the engulfed dolichol, possibly because of nonenzymatic free radical mediated decomposition. By means of a 1H-nuclear magnetic resonance (NMR) analytical method, the hypothesis was substantiated that dolichol may act as a free-radical scavenger in the cell membranes and protect polyunsaturated fatty acids from peroxidation, and that it may undergo decomposition in the process. (PMID 15741281) [HMDB]

CAS Number

118204-12-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	0.00022 g/L	ALOGPS
logP	9.77	ALOGPS
logP	22.42	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	16.33	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	336.81 m³·mol⁻¹	ChemAxon
Polarizability	134.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C70H114O

IUPAC name

(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55-tetradecamethylhexapentaconta-2,6,10,14,18,22,26,30,34,38,42,46,50,54-tetradecaen-1-ol

InChI Identifier

InChI=1S/C70H114O/c1-57(2)29-16-30-58(3)31-17-32-59(4)33-18-34-60(5)35-19-36-61(6)37-20-38-62(7)39-21-40-63(8)41-22-42-64(9)43-23-44-65(10)45-24-46-66(11)47-25-48-67(12)49-26-50-68(13)51-27-52-69(14)53-28-54-70(15)55-56-71/h29,31,33,35,37,39,41,43,45,47,49,51,53,55,71H,16-28,30,32,34,36,38,40,42,44,46,48,50,52,54,56H2,1-15H3/b58-31+,59-33+,60-35+,61-37+,62-39+,63-41+,64-43+,65-45+,66-47+,67-49+,68-51+,69-53+,70-55+

InChI Key

DLNRMPLOFNVUTQ-WIKVCOJLSA-N

Isomeric SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CO

Average Molecular Weight

971.6536

Monoisotopic Molecular Weight

970.88696827

Classification

Description

Belongs to the class of organic compounds known as polyprenols. These are prenols with more than 4 consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Polyprenols

Direct Parent

Polyprenols

Alternative Parents

Substituents

Polyterpenoid
Bactoprenol
Polyprenol skeleton
Fatty alcohol
Fatty acyl
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Subcellular:

Source:

Biological:

Animal

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Biochemical process:

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000009-edf5d7a54751edcd616a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0323313229-ba9ce09796a3fbe7dabb	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-3872164229-99abfbe7ffd6369d6c51	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000000009-8f7fd88207ab895eb230	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-0000000009-6b2aa23db5b793383f61	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ufr-1101010009-519da682fbb6cab36770	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000000009-c3dc8686054cabb3d4d5	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0000000019-a9a6fa9b941ea501fd79	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-1900000166-2129afee26cbd450f213	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-1100000049-d66e0f016aec3e6155e1	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01t9-1100131397-f7caf835178901bbb5e3	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0mdu-1015494731-28bdcf17f496e0e01f4c	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4947397

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

6443375

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB05181

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB