NP-MRD: Showing NP-Card for beta-1,4-Mannosyl-N-acetylglucosamine (NP0341759)

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Record Information

Version

2.0

Created at

2024-09-12 10:43:59 UTC

Updated at

2024-09-12 10:44:00 UTC

NP-MRD ID

NP0341759

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-1,4-Mannosyl-N-acetylglucosamine

Description

Beta-1,4-Mannosyl-N-acetylglucosamine, also known as beta-D-man-(1->4)-beta-D-glcnac or manb1-4glcnacb, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. Beta-1,4-Mannosyl-N-acetylglucosamine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304062012592D          

 26 27  0  0  1  0            999 V2000
   -3.2809   -0.7802    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2809   -1.6051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9953   -0.3678    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7096   -0.7802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9953    0.4571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5664    0.4571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8521   -0.7802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2809    0.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5664   -0.3678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7096    0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4240    0.4571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231    2.5197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375    2.1072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1375    1.2821    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4231    0.8694    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2914    1.2821    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2914    2.1072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4231    0.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0059    2.5197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8521    0.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0059    0.8695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7203    1.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4350    0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7203    2.1072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8521    2.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666    2.1072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  5  8  1  0  0  0  0
  3  1  1  0  0  0  0
  8  6  1  0  0  0  0
  1  9  1  0  0  0  0
  6  9  1  0  0  0  0
  1  2  1  1  0  0  0
  3  4  1  6  0  0  0
  5 10  1  1  0  0  0
  9  7  1  1  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  1  0  0  0
 17 19  1  1  0  0  0
 14 20  1  6  0  0  0
 16 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 13 25  1  1  0  0  0
 25 26  1  0  0  0  0
  6 20  1  1  0  0  0
M  END


  Mrv1652304062012592D          

 26 27  0  0  1  0            999 V2000
   -3.2809   -0.7802    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2809   -1.6051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9953   -0.3678    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7096   -0.7802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9953    0.4571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5664    0.4571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8521   -0.7802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2809    0.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5664   -0.3678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7096    0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4240    0.4571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231    2.5197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375    2.1072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1375    1.2821    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4231    0.8694    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2914    1.2821    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2914    2.1072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4231    0.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0059    2.5197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8521    0.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0059    0.8695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7203    1.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4350    0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7203    2.1072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8521    2.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666    2.1072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  5  8  1  0  0  0  0
  3  1  1  0  0  0  0
  8  6  1  0  0  0  0
  1  9  1  0  0  0  0
  6  9  1  0  0  0  0
  1  2  1  1  0  0  0
  3  4  1  6  0  0  0
  5 10  1  1  0  0  0
  9  7  1  1  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  1  0  0  0
 17 19  1  1  0  0  0
 14 20  1  6  0  0  0
 16 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 13 25  1  1  0  0  0
 25 26  1  0  0  0  0
  6 20  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0341759

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H25NO11/c1-4(18)15-7-9(20)12(6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8-,9-,10+,11+,12-,13-,14+/m1/s1

> <INCHI_KEY>
KFEUJDWYNGMDBV-JVHZDDNZSA-N

> <FORMULA>
C14H25NO11

> <MOLECULAR_WEIGHT>
383.35

> <EXACT_MASS>
383.142760629

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.16581188027758

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2R,3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide

> <ALOGPS_LOGP>
-2.80

> <JCHEM_LOGP>
-4.991410057333334

> <ALOGPS_LOGS>
-0.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.231138627153623

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.501288100055472

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083565282729

> <JCHEM_POLAR_SURFACE_AREA>
198.39999999999998

> <JCHEM_REFRACTIVITY>
79.43799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.59e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2R,3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0      -6.124  -1.456   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.124  -2.996   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -7.458  -0.687   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -8.791  -1.456   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -7.458   0.853   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.791   0.853   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.457  -1.456   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -6.124   1.623   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.791  -0.687   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.791   1.623   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -10.125   0.853   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.790   4.703   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.123   3.933   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.123   2.393   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.790   1.623   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.544   2.393   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.544   3.933   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.790   0.083   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.878   4.703   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.457   1.623   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       1.878   1.623   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       3.211   2.393   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.545   1.623   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.211   3.933   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.457   4.703   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.791   3.933   0.000  0.00  0.00           O+0
CONECT    1    3    9    2                                                  
CONECT    2    1                                                            
CONECT    3    5    1    4                                                  
CONECT    4    3                                                            
CONECT    5    3    8   10                                                  
CONECT    6    8    9   20                                                  
CONECT    7    9                                                            
CONECT    8    5    6                                                       
CONECT    9    1    6    7                                                  
CONECT   10    5   11                                                       
CONECT   11   10                                                            
CONECT   12   13   17                                                       
CONECT   13   12   14   25                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   12   19                                                  
CONECT   18   15                                                            
CONECT   19   17                                                            
CONECT   20   14    6                                                       
CONECT   21   16   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   13   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
2-Acetamido-2-deoxy-4-O-beta-D-mannopyranosyl-beta-D-glucopyranose	ChEBI
beta-D-Man-(1->4)-beta-D-glcnac	ChEBI
beta-D-Mannosyl-(1->4)-N-acetyl-beta-D-glucosamine	ChEBI
Manb1-4glcnacb	ChEBI
Manbeta1-4glcnacbeta	ChEBI
2-Acetamido-2-deoxy-4-O-b-D-mannopyranosyl-b-D-glucopyranose	Generator
2-Acetamido-2-deoxy-4-O-β-D-mannopyranosyl-β-D-glucopyranose	Generator
b-D-Man-(1->4)-b-D-glcnac	Generator
Β-D-man-(1->4)-β-D-glcnac	Generator
b-D-Mannosyl-(1->4)-N-acetyl-b-D-glucosamine	Generator
Β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosamine	Generator
b-1,4-Mannosyl-N-acetylglucosamine	Generator
Β-1,4-mannosyl-N-acetylglucosamine	Generator
2-(Acetylamino)-2-deoxy-4-O-beta-D-mannopyranosyl-beta-D-glucopyranose	HMDB
2-(Acetylamino)-2-deoxy-4-O-β-D-mannopyranosyl-β-D-glucopyranose	HMDB
4-O-Mannopyranosyl-N-acetylglucosamine	HMDB
4-O-beta-D-Mannopyranosyl-N-acetyl-D-glucosamine	HMDB
4-O-Β-D-mannopyranosyl-N-acetyl-D-glucosamine	HMDB
Man(beta1-4)glcnac	HMDB
Man(β1-4)glcnac	HMDB
Man-glcnac	HMDB
Man-beta-1,4-glcnac	HMDB
Man-β-1,4-glcnac	HMDB
Manp(beta1-4)glcpnac	HMDB
Manp(β1-4)glcpnac	HMDB
Manp-glcpnac	HMDB
Manp-beta-1,4-glcpnac	HMDB
Manp-β-1,4-glcpnac	HMDB
beta-1,4-D-Mannosyl-N-acetyl-D-glucosamine	HMDB
beta-D-Man-(1→4)-beta-D-glcnac	HMDB
beta-D-Mannopyranosyl-(1→4)-2-acetamido-2-deoxy-beta-D-glucopyranose	HMDB
beta-D-Mannosyl-(1→4)-N-acetyl-beta-D-glucosamine	HMDB
beta-D-Manp-(1→4)-beta-D-glcpnac	HMDB
Β-1,4-D-mannosyl-N-acetyl-D-glucosamine	HMDB
Β-D-man-(1→4)-β-D-glcnac	HMDB
Β-D-mannopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranose	HMDB
Β-D-mannosyl-(1→4)-N-acetyl-β-D-glucosamine	HMDB
Β-D-manp-(1→4)-β-D-glcpnac	HMDB
beta-1,4-Mannosyl-N-acetylglucosamine	HMDB
b-D-Manp-(1->4)-b-D-glcpnac	Generator
Β-D-manp-(1->4)-β-D-glcpnac	Generator

Chemical Formula

C₁₄H₂₅NO₁₁

Average Mass

383.3500 Da

Monoisotopic Mass

383.14276 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H]1O

InChI Identifier

InChI=1S/C14H25NO11/c1-4(18)15-7-9(20)12(6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8-,9-,10+,11+,12-,13-,14+/m1/s1

InChI Key

KFEUJDWYNGMDBV-JVHZDDNZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Acylaminosugar
N-acyl-alpha-hexosamine
Disaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Acetamide
Carboxamide group
Hemiacetal
Secondary carboxylic acid amide
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Alcohol
Primary alcohol
Organonitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

beta-D-Manp-(1->4)-D-GlcpNAc (CHEBI:71553 )

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	-2.8	ALOGPS
logP	-5	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	11.5	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	198.4 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.44 m³·mol⁻¹	ChemAxon
Polarizability	36.17 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0006535

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023964

KNApSAcK ID

Not Available

Chemspider ID

28533652

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70698368

PDB ID

Not Available

ChEBI ID

71553

Good Scents ID

Not Available

References

General References

Showing NP-Card for beta-1,4-Mannosyl-N-acetylglucosamine (NP0341759)

MOL for NP0341759 (beta-1,4-Mannosyl-N-acetylglucosamine)

3D MOL for NP0341759 (beta-1,4-Mannosyl-N-acetylglucosamine)

3D SDF for NP0341759 (beta-1,4-Mannosyl-N-acetylglucosamine)

3D-SDF for NP0341759 (beta-1,4-Mannosyl-N-acetylglucosamine)

PDB for NP0341759 (beta-1,4-Mannosyl-N-acetylglucosamine)

3D PDB for NP0341759 (beta-1,4-Mannosyl-N-acetylglucosamine)

SMILES for NP0341759 (beta-1,4-Mannosyl-N-acetylglucosamine)

INCHI for NP0341759 (beta-1,4-Mannosyl-N-acetylglucosamine)

Structure for NP0341759 (beta-1,4-Mannosyl-N-acetylglucosamine)

3D Structure for NP0341759 (beta-1,4-Mannosyl-N-acetylglucosamine)