NP-MRD: Showing NP-Card for alpha-D-Mannose (NP0044228)

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Record Information

Version

1.0

Created at

2022-01-25 16:47:00 UTC

Updated at

2022-01-25 16:54:25 UTC

NP-MRD ID

NP0044228

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-D-Mannose

Description

D-Mannose, also known as alpha-D-man or α-D-man, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. In humans, D-mannose is involved in the fructose intolerance, hereditary pathway. D-Mannose is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 2010 (PMID: 19844703). Based on a literature review a significant number of articles have been published on D-Mannose (PMID: 34600651) (PMID: 34564170) (PMID: 34561933) (PMID: 34537298).

Structure

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

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0       0.667  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.667  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.000  -0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.001   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.334   2.310   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.334  -0.770   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.667   2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.001   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.000   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.334   1.540   0.000  0.00  0.00           O+0
CONECT    1    3   10    2                                                  
CONECT    2    1                                                            
CONECT    3    5    1    4                                                  
CONECT    4    3                                                            
CONECT    5    3    9   11                                                  
CONECT    6    9   10    7                                                  
CONECT    7    6                                                            
CONECT    8   10                                                            
CONECT    9    5    6                                                       
CONECT   10    1    6    8                                                  
CONECT   11    5   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol

Synonyms

Value	Source
alpha-D-Man	ChEBI
alpha-D-Mannopyranose	ChEBI
WURCS=2.0/1,1,0/[a1122h-1a_1-5]/1/	ChEBI
a-D-Man	Generator
Α-D-man	Generator
a-D-Mannopyranose	Generator
Α-D-mannopyranose	Generator
a-D-Mannose	HMDB
Α-D-mannose	HMDB
(+)-Mannose	HMDB
Carubinose	HMDB
D(+)-Mannose	HMDB
Mannose	HMDB
Seminose	HMDB
alpha-D-Mannose	HMDB
alpha-Mannose	HMDB
Α-mannose	HMDB

Chemical Formula

C₆H₁₂O₆

Average Mass

180.1559 Da

Monoisotopic Mass

180.06339 Da

IUPAC Name

(2S,3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

Traditional Name

α-D-mannose

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5+,6+/m1/s1

InChI Key

WQZGKKKJIJFFOK-PQMKYFCFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2022-01-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, experimental)	Ahselim			2022-01-25	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cannabis sativa	CannabisDB	Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-mannopyranose (CHEBI:28729 )

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	-2.6	ALOGPS
logP	-2.9	ChemAxon
logS	0.64	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.92 m³·mol⁻¹	ChemAxon
Polarizability	16.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000169

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Mannose

METLIN ID

Not Available

PubChem Compound

185698

PDB ID

Not Available

ChEBI ID

28729

Good Scents ID

Not Available

References

General References

Ohashi T, Takegawa K: N- and O-linked oligosaccharides completely lack galactose residues in the gms1och1 mutant of Schizosaccharomyces pombe. Appl Microbiol Biotechnol. 2010 Mar;86(1):263-72. doi: 10.1007/s00253-009-2297-9. Epub 2009 Oct 21. [PubMed:19844703 ]
Faggian M, Bernabe G, Valente M, Francescato S, Baratto G, Brun P, Castagliuolo I, Dall'Acqua S, Peron G: Characterization of PACs profile and bioactivity of a novel nutraceutical combining cranberry extracts with different PAC-A oligomers, D-mannose and ascorbic acid: An in vivo/ex vivo evaluation of dual mechanism of action on intestinal barrier and urinary epithelium. Food Res Int. 2021 Nov;149:110649. doi: 10.1016/j.foodres.2021.110649. Epub 2021 Aug 20. [PubMed:34600651 ]
Sigida EN, Ibrahim IM, Kokoulin MS, Abulreesh HH, Elbanna K, Konnova SA, Fedonenko YP: Structure of the 4-O-[1-Carboxyethyl]-d-Mannose-Containing O-Specific Polysaccharide of a Halophilic Bacterium Salinivibrio sp. EG9S8QL. Mar Drugs. 2021 Sep 7;19(9). pii: md19090508. doi: 10.3390/md19090508. [PubMed:34564170 ]
Zhou X, Zheng Y, Sun W, Zhang Z, Liu J, Yang W, Yuan W, Yi Y, Wang J, Liu J: D-mannose alleviates osteoarthritis progression by inhibiting chondrocyte ferroptosis in a HIF-2alpha-dependent manner. Cell Prolif. 2021 Nov;54(11):e13134. doi: 10.1111/cpr.13134. Epub 2021 Sep 25. [PubMed:34561933 ]
Kasimova AA, Arbatsky NP, Timoshina OY, Shneider MM, Shashkov AS, Chizhov AO, Popova AV, Hall RM, Kenyon JJ, Knirel YA: The K26 capsular polysaccharide from Acinetobacter baumannii KZ-1098: Structure and cleavage by a specific phage depolymerase. Int J Biol Macromol. 2021 Nov 30;191:182-191. doi: 10.1016/j.ijbiomac.2021.09.073. Epub 2021 Sep 16. [PubMed:34537298 ]

Showing NP-Card for alpha-D-Mannose (NP0044228)

MOL for NP0044228 (alpha-D-Mannose)

3D MOL for NP0044228 (alpha-D-Mannose)

3D SDF for NP0044228 (alpha-D-Mannose)

3D-SDF for NP0044228 (alpha-D-Mannose)

PDB for NP0044228 (alpha-D-Mannose)

3D PDB for NP0044228 (alpha-D-Mannose)

SMILES for NP0044228 (alpha-D-Mannose)

INCHI for NP0044228 (alpha-D-Mannose)

Structure for NP0044228 (alpha-D-Mannose)

3D Structure for NP0044228 (alpha-D-Mannose)