Np mrd loader

Showing NP-Card for Arabinofuranose (NP0334814)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2024-09-10 20:04:41 UTC
Updated at2024-09-10 20:04:41 UTC
NP-MRD IDNP0334814
Secondary Accession NumbersNone
Natural Product Identification
Common NameArabinofuranose
DescriptionArabinofuranose belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Arabinofuranose is an extremely weak basic (essentially neutral) compound (based on its pKa). Arabinofuranose was first documented in 2001 (PMID: 11206446). The five-membered ring form of L-arabinose (PMID: 22499274) (PMID: 22549013) (PMID: 24036380).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0334814 (Arabinofuranose)


  Mrv0541 02241203562D          

 10 10  0  0  1  0            999 V2000
   11.9418   -6.3449    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1958   -7.1298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6092   -5.8596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1417   -6.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0226   -7.1298    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9759   -7.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2766   -6.3449    0.0000 C   0  0  3  0  0  0  0  0  0  0  0  0
   10.4288   -6.5345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2273   -7.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0653   -6.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  1  1  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  6  0  0  0
  7 10  1  4  0  0  0
  5  7  1  0  0  0  0
M  END
Download

3D MOL for NP0334814 (Arabinofuranose)

Download
3D SDF for NP0334814 (Arabinofuranose)

  Mrv0541 02241203562D          

 10 10  0  0  1  0            999 V2000
   11.9418   -6.3449    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1958   -7.1298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6092   -5.8596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1417   -6.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0226   -7.1298    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9759   -7.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2766   -6.3449    0.0000 C   0  0  3  0  0  0  0  0  0  0  0  0
   10.4288   -6.5345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2273   -7.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0653   -6.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  1  1  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  6  0  0  0
  7 10  1  4  0  0  0
  5  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334814

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O5/c6-1-2-3(7)4(8)5(9)10-2/h2-9H,1H2/t2-,3-,4+,5?/m0/s1

> <INCHI_KEY>
HMFHBZSHGGEWLO-HWQSCIPKSA-N

> <FORMULA>
C5H10O5

> <MOLECULAR_WEIGHT>
150.1299

> <EXACT_MASS>
150.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
13.508750288892614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4R,5S)-5-(hydroxymethyl)oxolane-2,3,4-triol

> <ALOGPS_LOGP>
-2.65

> <JCHEM_LOGP>
-2.302204276

> <ALOGPS_LOGS>
0.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.899514700313038

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.30569577774193

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9811390578102284

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
29.96089999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-arabinofuranose

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0334814 (Arabinofuranose)
Download
PDB for NP0334814 (Arabinofuranose)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      22.291 -11.844   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.765 -13.309   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      23.537 -10.938   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      20.798 -11.433   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.309 -13.309   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      22.355 -14.788   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      24.783 -11.844   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      19.467 -12.198   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      24.691 -14.788   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      26.255 -11.433   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9    7                                                  
CONECT    6    2                                                            
CONECT    7    3   10    5                                                  
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

Download
3D PDB for NP0334814 (Arabinofuranose)
Download
SMILES for NP0334814 (Arabinofuranose)
OC[C@@H]1OC(O)[C@H](O)[C@H]1O
Download
INCHI for NP0334814 (Arabinofuranose)
InChI=1S/C5H10O5/c6-1-2-3(7)4(8)5(9)10-2/h2-9H,1H2/t2-,3-,4+,5?/m0/s1
Download
View in JSmol
Synonyms
ValueSource
L-ArabinofuranoseHMDB
ArabinofuranoseMeSH
Chemical FormulaC5H10O5
Average Mass150.1299 Da
Monoisotopic Mass150.05282 Da
IUPAC Name(3R,4R,5S)-5-(hydroxymethyl)oxolane-2,3,4-triol
Traditional NameL-arabinofuranose
CAS Registry NumberNot Available
SMILES
OC[C@@H]1OC(O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C5H10O5/c6-1-2-3(7)4(8)5(9)10-2/h2-9H,1H2/t2-,3-,4+,5?/m0/s1
InChI KeyHMFHBZSHGGEWLO-HWQSCIPKSA-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 pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentPentoses  
Alternative Parents
Substituents
  • Pentose monosaccharide
    • 

  • Tetrahydrofuran
    • 

  • Secondary alcohol
    • 

  • Hemiacetal
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • 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-2.6ALOGPS
logP-2.3ChemAxon
logS0.85ALOGPS
pKa (Strongest Acidic)11.31ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity29.96 m³·mol⁻¹ChemAxon
Polarizability13.51 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012325  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028944  
KNApSAcK IDNot Available
Chemspider ID389751  
KEGG Compound IDC06115  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440921  
PDB IDNot Available
ChEBI ID6178  
Good Scents IDNot Available
References
General References
  1. Zhang Q, Liu HW: Chemical synthesis of UDP-beta-L-arabinofuranose and its turnover to UDP-beta-L-arabinopyranose by UDP-galactopyranose mutase. Bioorg Med Chem Lett. 2001 Jan 22;11(2):145-9. doi:  10.1016/s0960-894x(00)00616-8. [PubMed:11206446  ] 
  2. Poulin MB, Zhou R, Lowary TL: Synthetic UDP-galactofuranose analogs reveal critical enzyme-substrate interactions in GlfT2-catalyzed mycobacterial galactan assembly. Org Biomol Chem. 2012 May 28;10(20):4074-87. doi: 10.1039/c2ob25159k. Epub 2012  Apr 13. [PubMed:22499274  ] 
  3. Golovchenko VV, Khramova DS, Shashkov AS, Otgonbayar D, Chimidsogzol A, Ovodov YS: Structural characterisation of the polysaccharides from endemic Mongolian desert plants and their effect on the intestinal absorption of ovalbumin. Carbohydr Res. 2012 Jul 15;356:265-72. doi: 10.1016/j.carres.2012.03.023. Epub  2012 Apr 10. [PubMed:22549013  ] 
  4. da Paixao Soares F, Silva MJ, Doboszewski B: Deoxygenation at the C3 position of D- and L-arabinofuranose: stereospecific access to enantiomeric cordycepose derivatives. Carbohydr Res. 2013 Oct 18;380:143-8. doi: 10.1016/j.carres.2013.07.017. Epub  2013 Aug 9. [PubMed:24036380  ]