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Showing NP-Card for beta-D-Fucose (NP0334617)

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Record Information
Version2.0
Created at2024-09-10 19:09:40 UTC
Updated at2024-09-10 19:09:40 UTC
NP-MRD IDNP0334617
Secondary Accession NumbersNone
Natural Product Identification
Common Namebeta-D-Fucose
DescriptionBeta-D-Fucose, also known as b-D-fuc or beta-delta-fuc, 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. beta-D-Fucose was first documented in 1981 (PMID: 6789883). Beta-D-Fucose is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 6812077).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334617 (beta-D-Fucose)


  Mrv0541 02231217232D          

 11 11  0  0  1  0            999 V2000
   -0.8444    1.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1299    1.0500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5846    1.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    1.0500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0135    1.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.2250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0135   -0.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5845   -0.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5845   -1.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1299    0.2251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8444   -0.1874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
M  END
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3D MOL for NP0334617 (beta-D-Fucose)

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3D SDF for NP0334617 (beta-D-Fucose)

  Mrv0541 02231217232D          

 11 11  0  0  1  0            999 V2000
   -0.8444    1.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1299    1.0500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5846    1.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    1.0500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0135    1.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.2250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0135   -0.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5845   -0.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5845   -1.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1299    0.2251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8444   -0.1874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0334617

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6-/m1/s1

> <INCHI_KEY>
SHZGCJCMOBCMKK-FPRJBGLDSA-N

> <FORMULA>
C6H12O5

> <MOLECULAR_WEIGHT>
164.1565

> <EXACT_MASS>
164.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
15.281244896234004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5R,6R)-6-methyloxane-2,3,4,5-tetrol

> <ALOGPS_LOGP>
-2.39

> <JCHEM_LOGP>
-1.885629251333333

> <ALOGPS_LOGS>
0.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.724419195509512

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.30218058050956

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121738272477764

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
34.3797

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.27e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-D-fucose

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334617 (beta-D-Fucose)
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PDB for NP0334617 (beta-D-Fucose)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.576   2.730   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.242   1.960   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.091   2.730   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.425   1.960   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.759   2.730   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.425   0.420   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.759  -0.350   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.091  -0.350   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.091  -1.890   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.242   0.420   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.576  -0.350   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    2   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0334617 (beta-D-Fucose)
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SMILES for NP0334617 (beta-D-Fucose)
C[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O
Download
INCHI for NP0334617 (beta-D-Fucose)
InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6-/m1/s1
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View in JSmol
Synonyms
ValueSource
beta-D-FucChEBI
b-D-FucGenerator
Β-D-fucGenerator
b-D-FucoseGenerator
Β-D-fucoseGenerator
6-Deoxy-beta-D-galactopyranoseHMDB
6-Deoxy-beta-delta-galactopyranoseHMDB
b-D-FucopyranoseHMDB
beta-D-FucopyranoseHMDB
beta-delta-FucHMDB
beta-delta-FucopyranoseHMDB
FCBHMDB
6-Deoxy-beta-D-galactoseHMDB
6-Deoxy-β-D-galactopyranoseHMDB
6-Deoxy-β-D-galactoseHMDB
Β-D-fucopyranoseHMDB
beta-D-FucoseHMDB
Chemical FormulaC6H12O5
Average Mass164.1565 Da
Monoisotopic Mass164.06847 Da
IUPAC Name(2R,3R,4S,5R,6R)-6-methyloxane-2,3,4,5-tetrol
Traditional Nameβ-D-fucose
CAS Registry NumberNot Available
SMILES
C[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6-/m1/s1
InChI KeySHZGCJCMOBCMKK-FPRJBGLDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot 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.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentHexoses  
Alternative Parents
Substituents
  • Hexose monosaccharide
    • 

  • Oxane
    • 

  • Secondary alcohol
    • 

  • Hemiacetal
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.4ALOGPS
logP-1.9ChemAxon
logS0.7ALOGPS
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.38 m³·mol⁻¹ChemAxon
Polarizability15.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003081  
DrugBank IDDB04062  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023106  
KNApSAcK IDNot Available
Chemspider ID388721  
KEGG Compound IDC02095  
BioCyc IDCPD-13293  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3284  
PubChem Compound439650  
PDB IDNot Available
ChEBI ID27442  
Good Scents IDNot Available
References
General References
  1. Wiederschain GYa, Beyer EM, Klyashchitsky BA, Shashkov AS: Specificity patterns of different types of human fucosidase. Recognition of a certain region of the pyranose ring in sugars by the enzymes. Biochim Biophys Acta. 1981 Jun 15;659(2):434-44. doi:  10.1016/0005-2744(81)90069-3. [PubMed:6789883  ] 
  2. Daniels LB, Gnarra JR, Glew RH: Effectors of three beta-glucosidases from human liver. Prog Clin Biol Res. 1982;95:333-55. [PubMed:6812077  ]