Showing Compound Dolichyl phosphate D-mannose (FDB022356)

Record Information

Version

1.0

Creation date

2011-09-21 00:12:41 UTC

Update date

2015-07-21 06:57:10 UTC

Primary ID

FDB022356

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Dolichyl phosphate D-mannose

Description

Dolichyl phosphate D-mannose (DPM) is an intermediate in the biosynthesis of N-glycans. It is a substrate for dolichol-phosphate mannosyltransferase (PMID: 10835346). Dolichol-phosphate mannosyltransferase is a heterotrimeric protein embedded in the endoplasmic reticulum membrane. The first subunit of the heterotrimer appears to be the actual catalyst, and the other two subunits appear to stabilize it. More specifically, dolichol-phosphate-mannose is the donor of mannose groups in the synthesis of the dolichol pyrophosphate-linked precursor oligosaccharide in asparagine-linked glycosylation, in the synthesis of glycosyl phosphatidylinositol (GPI) anchor precursors, in protein O-mannosylation and in protein C-mannosylation. Its synthesis proceeds in two steps. First, cytosolic GDP-mannose reacts with dolichol phosphate exposed on the cytosolic face of the endoplasmic reticulum membrane to form DPM with its mannose moiety oriented toward the cytosol. The DPM molecule then flips in the endoplasmic reticulum membrane, so that its mannose moiety is in the endoplasmic reticulum lumen, accessible to the enzymes that catalyze its transfer to growing glycolipids and glycoproteins. (PMID: 11102867). Dolichyl phosphate D-mannose is also a substrate for protein O-mannosyl-transferase 2 and protein O-mannosyl-transferase 1. [HMDB]

CAS Number

908211-94-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
Dolichol ate mannose	HMDB
Dolichol phosphate mannose	HMDB
dolichol phosphate mannose	hmdb
Dolichyl ate D-mannose	HMDB
Dolichyl D-mannosyl ate	HMDB
Dolichyl D-mannosyl phosphate	HMDB
Dolichyl phosphoric acid D-mannose	Generator
DPM	HMDB
{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonate	HMDB

Showing 1 to 9 of 9 entries

Predicted Properties

Property	Value	Source
Water Solubility	32.3 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.1	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	1.16	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.8 m³·mol⁻¹	ChemAxon
Polarizability	20.33 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H13O9P

IUPAC name

{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

InChI Identifier

InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6+/m1/s1

InChI Key

HXXFSFRBOHSIMQ-PQMKYFCFSA-N

Isomeric SMILES

OC[C@H]1O[C@@H](OP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1O

Average Molecular Weight

260.1358

Monoisotopic Molecular Weight

260.029718526

Classification

Description

Belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharide phosphates

Alternative Parents

Substituents

Hexose monosaccharide
Monosaccharide phosphate
Monoalkyl phosphate
Organic phosphoric acid derivative
Oxane
Alkyl phosphate
Phosphoric acid ester
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Primary alcohol
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Source:

Endogenous

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

Type	Description	Splash Key	View
Predicted GC-MS	Dolichyl phosphate D-mannose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9320000000-a09e98e90da0a3c66173	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-003u-3892380000-6f3044d9c3f952cf4b44	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_3_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dolichyl phosphate D-mannose, TMS_3_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9130000000-0173720981b7b1d7a5d8	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9240000000-d27275e74b0283c592dc	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9100000000-8389331fb0da3c617f2f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6s-8290000000-5d7e82085dc2e86c5bb7	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9010000000-03c6ff3c1e1b1a23255e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-38e837f16bac5f0ceade	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0290000000-b59137504dd85ff7bcbf	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-5920000000-50b89ef6664d51ebdb62	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-9000000000-448e77bbc693c887ac18	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-3090000000-69c93c84647ca924108a	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9010000000-0d6df09e6f12d66f281c	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-f53a8156649b945c2aee	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00994

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

1809321

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

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SuperScent ID

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Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

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Old DFC IDS

Not Available

Associated Foods

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Biological Effects and Interactions

Health Effects / Bioactivities

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Enzymes

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Pathways

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Metabolism

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Biosynthesis

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Organoleptic Properties

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Files

MSDS

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References

Synthesis Reference

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General Reference

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Content Reference

Showing Compound Dolichyl phosphate D-mannose (FDB022356)

Structure for FDB022356 (Dolichyl phosphate D-mannose)