Cannabis Compound Database: Showing Compound Card for Guanosine diphosphate mannose (CDB004886)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (8) Show 8 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:46:59 UTC

Updated at

2020-11-18 16:38:55 UTC

CannabisDB ID

CDB004886

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Guanosine diphosphate mannose

Description

Guanosine diphosphate mannose, also known as gdpmannose or GDP-alpha-D-mannose, belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. Guanosine diphosphate mannose is a strong basic compound (based on its pKa). Guanosine diphosphate mannose exists in all living species, ranging from bacteria to humans. Within humans, guanosine diphosphate mannose participates in a number of enzymatic reactions. In particular, guanosine diphosphate mannose can be biosynthesized from D-mannose 1-phosphate through its interaction with the enzyme mannose-1-phosphate guanyltransferase beta. In addition, guanosine diphosphate mannose can be converted into GDP-4-dehydro-6-deoxy-D-mannose; which is catalyzed by the enzyme GDP-mannose 4,6 dehydratase. In humans, guanosine diphosphate mannose is involved in the metabolic disorder called fructosuria. Outside of the human body, Guanosine diphosphate mannose has been detected, but not quantified in, several different foods, such as other bread, feijoa, chanterelles, cherimoya, and romaine lettuces. This could make guanosine diphosphate mannose a potential biomarker for the consumption of these foods. The alpha-anomer of GDP-D-mannose. Guanosine diphosphate mannose is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
GDP-D-Mannose	ChEBI
GDPmannose	ChEBI
Guanosine 5'-(trihydrogen diphosphate), mono-alpha-D-mannopyranosyl ester	ChEBI
Guanosine diphosphomannose	ChEBI
Guanosine pyrophosphate mannose	ChEBI
GDP-alpha-D-Mannose	Kegg
Guanosine 5'-(trihydrogen diphosphate), mono-a-D-mannopyranosyl ester	Generator
Guanosine 5'-(trihydrogen diphosphate), mono-α-D-mannopyranosyl ester	Generator
Guanosine 5'-(trihydrogen diphosphoric acid), mono-a-D-mannopyranosyl ester	Generator
Guanosine 5'-(trihydrogen diphosphoric acid), mono-alpha-D-mannopyranosyl ester	Generator
Guanosine 5'-(trihydrogen diphosphoric acid), mono-α-D-mannopyranosyl ester	Generator
Guanosine pyrophosphoric acid mannose	Generator
GDP-a-D-Mannose	Generator
GDP-Α-D-mannose	Generator
Guanosine diphosphoric acid mannose	Generator
GDP Mannose	HMDB
GDP-Glucose	HMDB
GDP-Mannose	HMDB
Pyrophosphate mannose, guanosine	HMDB
Diphosphomannose, guanosine	HMDB
Mannose, guanosine diphosphate	HMDB
Diphosphate mannose, guanosine	HMDB
Mannose, guanosine pyrophosphate	HMDB
Mannose, GDP	HMDB
Guanosine 5'-(trihydrogen diphosphate) p'-mannosyl ester	HMDB
Guanosine 5'-(trihydrogen pyrophosphate) mono-D-mannosyl ester	HMDB
Guanosine 5'-(trihydrogen pyrophosphate) monomannopyranosyl ester	HMDB
Guanosine 5'-(trihydrogen pyrophosphate) monomannosyl ester	HMDB
Guanosine 5'-diphosphate D-mannose	HMDB
Guanosine 5'-pyrophosphate D-mannosyl ester	HMDB
Guanosine 5'-pyrophosphate alpha-D-mannosyl ester	HMDB
Guanosine 5'-pyrophosphate α-D-mannosyl ester	HMDB
Guanosine 5’-(trihydrogen diphosphate) p’-mannosyl ester	HMDB
Guanosine 5’-(trihydrogen pyrophosphate) mono-D-mannosyl ester	HMDB
Guanosine 5’-(trihydrogen pyrophosphate) monomannopyranosyl ester	HMDB
Guanosine 5’-(trihydrogen pyrophosphate) monomannosyl ester	HMDB
Guanosine 5’-diphosphate D-mannose	HMDB
Guanosine 5’-pyrophosphate D-mannosyl ester	HMDB
Guanosine 5’-pyrophosphate α-D-mannosyl ester	HMDB
Guanosine diphosphate mannose	HMDB

Chemical Formula

C₁₆H₂₅N₅O₁₆P₂

Average Molecular Weight

605.34

Monoisotopic Molecular Weight

605.0772

IUPAC Name

[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

Traditional Name

guanosine diphosphomannose

CAS Registry Number

20236-92-4

SMILES

NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C(=O)N1

InChI Identifier

InChI=1S/C16H25N5O16P2/c17-16-19-12-6(13(28)20-16)18-3-21(12)14-10(26)8(24)5(34-14)2-33-38(29,30)37-39(31,32)36-15-11(27)9(25)7(23)4(1-22)35-15/h3-5,7-11,14-15,22-27H,1-2H2,(H,29,30)(H,31,32)(H3,17,19,20,28)/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1

InChI Key

MVMSCBBUIHUTGJ-GDJBGNAASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine nucleotide sugars

Direct Parent

Purine nucleotide sugars

Alternative Parents

Substituents

Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Hydroxypyrimidine
Monoalkyl phosphate
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Pyrimidine
Heteroaromatic compound
Tetrahydrofuran
Imidazole
Azole
Secondary alcohol
Polyol
Oxacycle
Organoheterocyclic compound
Azacycle
Organic oxygen compound
Alcohol
Organic oxide
Primary alcohol
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

GDP-D-mannose (CHEBI:15820 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Fabaceae

Animal

Biological location:

Subcellular:

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-1.8	ALOGPS
logP	-5.3	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	327.43 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	118.51 m³·mol⁻¹	ChemAxon
Polarizability	48.72 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Guanosine diphosphate mannose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05bu-5842490000-d73f755e03b8ad234b29	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01r6-7882509000-02adbc06a0f79e803d88	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_1_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Guanosine diphosphate mannose, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 32V, positive	splash10-0a4i-0000209000-fa2b35ba4f2fbdff74a3	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 32V, negative	splash10-0udi-3401309000-93213e14894fde4ba5c2	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0001309000-586a7f020650fe518e5f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0900000000-bba5489b865ff8d5ba78	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0100900000-d5b51af9c9e096503197	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900400000-3410bfae1c82b5e08999	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00b9-9434300000-661dad8f3e9cd9b10a38	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000009000-c84788b57e1d68c3a299	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0910510000-30a5518df6f0f53ad7b7	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0910000000-48aef418f3aa94cc35f8	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-1900000000-438261daf883fac47d6c	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-1901325000-e5d0bcd5db4a59b606f8	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1901100000-a8c00836fd0ca5a71ad1	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pdl-3900000000-358726d071759c859d9e	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000009000-3f663b5fce4f431e1e25	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-4701986000-bb5e3a66be23d7de55e6	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05i0-3911810000-ee275d8a12bcf1e5065c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900002000-37d2f661727ecc1c915a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900001000-de8f3c7c7e6a620f0e90	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udr-2930000000-7a0fc600f843201b86c4	2021-09-24	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Fructose and Mannose Degradation
Fructosuria		Not Available
Fructose intolerance, hereditary		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Alpha-1,3/1,6-mannosyltransferase ALG2	ALG2	9q22.33	Q9H553	details
Dolichol-phosphate mannosyltransferase	DPM1	20q13.13	O60762	details
GDP-mannose 4,6 dehydratase	GMDS	6p25	O60547	details
Chitobiosyldiphosphodolichol beta-mannosyltransferase	ALG1	16p13.3	Q9BT22	details
Mannose-1-phosphate guanyltransferase beta	GMPPB	3p21.31	Q9Y5P6	details
Mannose-1-phosphate guanyltransferase alpha	GMPPA	2q35	Q96IJ6	details
GDP-Man:Man(3)GlcNAc(2)-PP-Dol alpha-1,2-mannosyltransferase	ALG11	13q14.2	Q2TAA5	details
Dolichol-phosphate mannosyltransferase subunit 3	DPM3		Q9P2X0	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001163

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Guanosine diphosphate mannose

METLIN ID

6045

PubChem Compound

18396

PDB ID

Not Available

ChEBI ID

15820

References

General References

Not Available

Enzymes

Enzyme Details

1. Alpha-1,3/1,6-mannosyltransferase ALG2

General function:: Involved in biosynthetic process
Specific function:: Mannosylates Man(2)GlcNAc(2)-dolichol diphosphate and Man(1)GlcNAc(2)-dolichol diphosphate to form Man(3)GlcNAc(2)-dolichol diphosphate.
Gene Name:: ALG2
Uniprot ID:: Q9H553
Molecular weight:: 47091.075

Enzyme Details

2. 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

3. GDP-mannose 4,6 dehydratase

General function:: Involved in catalytic activity
Specific function:: Conversion of GDP-D-mannose to GDP-4-keto-6-D-deoxymannose.
Gene Name:: GMDS
Uniprot ID:: O60547
Molecular weight:: 39053.295

Enzyme Details

4. Chitobiosyldiphosphodolichol beta-mannosyltransferase

General function:: Involved in biosynthetic process
Specific function:: Participates in the formation of the lipid-linked precursor oligosaccharide for N-glycosylation. Involved in assembling the dolichol-pyrophosphate-GlcNAc(2)-Man(5) intermediate on the cytoplasmic surface of the ER.
Gene Name:: ALG1
Uniprot ID:: Q9BT22
Molecular weight:: 52517.685

Enzyme Details

5. Mannose-1-phosphate guanyltransferase beta

General function:: Involved in transferase activity
Specific function:: Not Available
Gene Name:: GMPPB
Uniprot ID:: Q9Y5P6
Molecular weight:: 42649.34

Enzyme Details

6. Mannose-1-phosphate guanyltransferase alpha

General function:: Involved in transferase activity
Specific function:: Not Available
Gene Name:: GMPPA
Uniprot ID:: Q96IJ6
Molecular weight:: 46290.785

Enzyme Details

7. GDP-Man:Man(3)GlcNAc(2)-PP-Dol alpha-1,2-mannosyltransferase

General function:: Not Available
Specific function:: Mannosyltransferase involved in the last steps of the synthesis of Man5GlcNAc(2)-PP-dolichol core oligosaccharide on the cytoplasmic face of the endoplasmic reticulum. Catalyzes the addition of the 4th and 5th mannose residues to the dolichol-linked oligosaccharide chain.
Gene Name:: ALG11
Uniprot ID:: Q2TAA5
Molecular weight:: 55650.595

Enzyme Details

8. Dolichol-phosphate mannosyltransferase subunit 3

General function:: Not Available
Specific function:: Stabilizer subunit of the dolichol-phosphate-mannose synthase complex.
Gene Name:: DPM3
Uniprot ID:: Q9P2X0
Molecular weight:: Not Available

Showing Compound Card for Guanosine diphosphate mannose (CDB004886)

Structure for CDB004886 (Guanosine diphosphate mannose)

Enzymes