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Showing NP-Card for L-Arabinose (NP0000808)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:39:45 UTC
NP-MRD IDNP0000808
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Arabinose
DescriptionL-Arabinose (CAS: 5328-37-0) Belongs to the class of compounds known as aldopentoses. An aldopentose is a monosaccharide containing five carbon atoms, including an aldehyde (CHO) functional group. Arabinose gets its name from gum arabic, from which it was first isolate. Most saccharides found in nature are in the "D"-form, however, L-arabinose is in fact more common than D-arabinose. L-arabinose is found in nature as a component of biopolymers such as hemicellulose and pectin. L-arabinose is found in all organisms from bacteria to plants to animals. Arabinose is the second most abundant pentose in lignocellulosic biomass after xylose. There are two different arabinose utilization pathways in nature: Bacterial and fungal. The bacterial pathway converts arabinose into xylulose-5-P via ribulose-5-P using three enzymes (L-arabinose isomerase, L-ribulokinase, and L-ribulose-5-P 4-epimerase) after which it enters the pentose phosphate pathway for ethanol production. The fungal pathway converts arabinose into L-arabinitol by aldose reductase (AR) or XR, L-xylulose by L-arabinitol 4-dehydrogenase (LAD), xylitol by L-xylulose reductase (LXR), D-xylulose by xylulose dehydrogenase (XDH), and D-xylulose-5-P by xylulose kinase (XK), and lastly enters the nonoxidative pentose phosphate pathway for further metabolism. Arabinose has a sweet taste and is one of the most abundant components released by complete hydrolysis of non-starch polysaccharides (NSP) of vegetable origin. Although widely present in nature, L-arabinose is rarely used in food production or food flavoring, and its physiological effects in vivo have received little attention. L-arabinose is known to selectively inhibit intestinal sucrase activity in a non-competitive manner. Sucrase is the enzyme that breaks down sucrose into glucose and fructose in the small intestine. As a result, L-arabinose suppresses plasma glucose increase due to sucrose ingestion. The presence of arabinose in urine may indicate overgrowth of intestinal yeast such as Candida albicans or other yeast/fungus species. L-arabinose is also a microbial metabolite found in, and produced by, Mycobacterium (PMID: 16232643 ). In a rare case of two autistic brothers that were not associated with any known metabolic disease, it was found the median value for L-arabinose in their urine samples was 179 umol/mmol creatinine, nearly six times greater than normal children (PMID: 11238761 , 8931641 , 1390604 , 7628083 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000808 (L-Arabinose)


     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.8112    0.7892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4380    0.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0819    1.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580    2.0628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4419    1.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8150    0.4222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0858   -0.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496   -1.9223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541   -0.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5635   -1.7388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0206   -0.0981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2710   -1.0620    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5788    1.7403    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2457    3.1337    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2748    2.2733    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0244    1.3095    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5826   -0.5289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6227   -2.5260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3097   -2.1965    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3998   -3.2298    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  2 12  1  6
  3 13  1  6
  3 14  1  0
  5 15  1  1
  6 16  1  0
  7 17  1  1
  8 18  1  0
  9 19  1  6
 10 20  1  0
M  END
Download

3D MOL for NP0000808 (L-Arabinose)

HMDB0000646
     RDKit          3D
L-Arabinose
 20 20  0  0  0  0  0  0  0  0999 V2000
    2.3248   -0.1427    1.0373 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2314    0.1485    0.2488 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9860   -0.9479   -0.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2037   -0.9183   -1.3790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989   -0.5585   -0.6598 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3585   -0.3525   -1.5733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0790    0.7932    0.0097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4667    1.6228   -0.9451 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0064    0.5236    1.0610 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4049   -0.4976    1.8995 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1507    0.2498    0.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4865    1.0733   -0.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1758   -1.9486   -0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8025   -0.8793   -1.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6207   -1.2965    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1582   -0.8648   -1.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9812    1.2159    0.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0783    2.4347   -0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1783    1.4550    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3076   -1.1100    2.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  2 12  1  6
  3 13  1  0
  3 14  1  0
  5 15  1  1
  6 16  1  0
  7 17  1  1
  8 18  1  0
  9 19  1  1
 10 20  1  0
M  END
Download

3D SDF for NP0000808 (L-Arabinose)


     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.8112    0.7892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4380    0.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0819    1.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580    2.0628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4419    1.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8150    0.4222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0858   -0.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496   -1.9223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541   -0.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5635   -1.7388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0206   -0.0981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2710   -1.0620    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5788    1.7403    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2457    3.1337    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2748    2.2733    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0244    1.3095    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5826   -0.5289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6227   -2.5260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3097   -2.1965    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3998   -3.2298    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  2 12  1  6
  3 13  1  6
  3 14  1  0
  5 15  1  1
  6 16  1  0
  7 17  1  1
  8 18  1  0
  9 19  1  6
 10 20  1  0
M  END
> <DATABASE_ID>
NP0000808

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
SRBFZHDQGSBBOR-KLVWXMOXSA-N

> <FORMULA>
C5H10O5

> <MOLECULAR_WEIGHT>
150.1299

> <EXACT_MASS>
150.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
13.368574729203504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.57

> <JCHEM_LOGP>
-2.302204276

> <ALOGPS_LOGS>
0.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.78626315175902

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.31062424774241

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265718350182684

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
29.96089999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-L-arabinopyranose

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000808 (L-Arabinose)

HMDB0000646
     RDKit          3D
L-Arabinose
 20 20  0  0  0  0  0  0  0  0999 V2000
    2.3248   -0.1427    1.0373 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2314    0.1485    0.2488 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9860   -0.9479   -0.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2037   -0.9183   -1.3790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989   -0.5585   -0.6598 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3585   -0.3525   -1.5733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0790    0.7932    0.0097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4667    1.6228   -0.9451 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0064    0.5236    1.0610 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4049   -0.4976    1.8995 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1507    0.2498    0.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4865    1.0733   -0.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1758   -1.9486   -0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8025   -0.8793   -1.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6207   -1.2965    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1582   -0.8648   -1.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9812    1.2159    0.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0783    2.4347   -0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1783    1.4550    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3076   -1.1100    2.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  2 12  1  6
  3 13  1  0
  3 14  1  0
  5 15  1  1
  6 16  1  0
  7 17  1  1
  8 18  1  0
  9 19  1  1
 10 20  1  0
M  END
Download

PDB for NP0000808 (L-Arabinose)

HEADER    PROTEIN                                 08-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-JUL-20         0                                  
HETATM    1  O   UNK     0    8666.9928664.164   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8669.6588665.703   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8664.3248665.707   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8669.6558668.786   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8668.3258668.015   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8668.3258666.475   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8666.9918665.705   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.6588666.475   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.6588668.015   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8666.9918668.785   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    6                                                            
CONECT    3    8                                                            
CONECT    4    5                                                            
CONECT    5    6   10    4                                                  
CONECT    6    5    7    2                                                  
CONECT    7    6    8    1                                                  
CONECT    8    7    9    3                                                  
CONECT    9    8   10                                                       
CONECT   10    5    9                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for NP0000808 (L-Arabinose)

COMPND    HMDB0000646
HETATM    1  O1  UNL     1       2.325  -0.143   1.037  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.231   0.149   0.249  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.986  -0.948  -0.725  1.00  0.00           C  
HETATM    4  O2  UNL     1      -0.204  -0.918  -1.379  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.299  -0.559  -0.660  1.00  0.00           C  
HETATM    6  O3  UNL     1      -2.358  -0.352  -1.573  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.079   0.793   0.010  1.00  0.00           C  
HETATM    8  O4  UNL     1      -0.467   1.623  -0.945  1.00  0.00           O  
HETATM    9  C5  UNL     1       0.006   0.524   1.061  1.00  0.00           C  
HETATM   10  O5  UNL     1      -0.405  -0.498   1.900  1.00  0.00           O  
HETATM   11  H1  UNL     1       3.151   0.250   0.638  1.00  0.00           H  
HETATM   12  H2  UNL     1       1.486   1.073  -0.346  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.176  -1.949  -0.239  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.803  -0.879  -1.506  1.00  0.00           H  
HETATM   15  H5  UNL     1      -1.621  -1.297   0.111  1.00  0.00           H  
HETATM   16  H6  UNL     1      -3.158  -0.865  -1.307  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.981   1.216   0.438  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.078   2.435  -0.534  1.00  0.00           H  
HETATM   19  H9  UNL     1       0.178   1.455   1.599  1.00  0.00           H  
HETATM   20  H10 UNL     1       0.308  -1.110   2.173  1.00  0.00           H  
CONECT    1    2   11
CONECT    2    3    9   12
CONECT    3    4   13   14
CONECT    4    5
CONECT    5    6    7   15
CONECT    6   16
CONECT    7    8    9   17
CONECT    8   18
CONECT    9   10   19
CONECT   10   20
END
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SMILES for NP0000808 (L-Arabinose)

O[C@H]1CO[C@H](O)[C@H](O)[C@H]1O
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INCHI for NP0000808 (L-Arabinose)

InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4+,5-/m0/s1
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View in JSmol
Synonyms
ValueSource
BETA-L-ARABINOSEChEBI
WURCS=2.0/1,1,0/[a211h-1b_1-5]/1/ChEBI
b-L-ARABINOSEGenerator
Β-L-arabinoseGenerator
b-L-ArabinopyranoseHMDB
Β-L-arabinopyranoseHMDB
L-ArabinopyranoseHMDB
PectinoseHMDB
beta-L-ArabinopyranoseHMDB
ArabinopyranoseHMDB
ArabinoseHMDB
L-ArabinoseHMDB
Chemical FormulaC5H10O5
Average Mass150.1299 Da
Monoisotopic Mass150.05282 Da
IUPAC Name(2S,3R,4S,5S)-oxane-2,3,4,5-tetrol
Traditional Nameβ-L-arabinopyranose
CAS Registry Number5328-37-0
SMILES
O[C@H]1COC(O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4+,5?/m0/s1
InChI KeySRBFZHDQGSBBOR-HWQSCIPKSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acacia tortuosaPlant
Afraegle paniculataLOTUS Database
Aloe veraPlant
Anagallis arvensisLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaPlant
Averrhoa carambolaPlant
Bergera koenegii-
Beta vulgarisLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica oleracea L. ssp. BotrytisPlant
Bubalus bubalisFooDB
Cajanus cajanLOTUS Database
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
Citrus sinensisKNApSAcK Database
Citrus X sinensis (L.) Osbeck (pro. sp.)Plant
Codonopsis canescensPlant
Codonopsis pilosulaPlant
Codonopsis pilosula subsp. tangshenPlant
Codonopsis subglobosaPlant
Codonopsis tubulosaPlant
ColumbaFooDB
ColumbidaeFooDB
Cussonia spicataLOTUS Database
Cydonia oblongaFooDB
Dromaius novaehollandiaeFooDB
Elliottia paniculataLOTUS Database
Equus caballusFooDB
Gallus gallusFooDB
Helianthus annuusLOTUS Database
Homo sapiens (Urine)Animalia
Jatropha gossypifoliaLOTUS Database
Lagopus mutaFooDB
Larix laricinaLOTUS Database
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Linum usitatissimumFooDB
Medicago lupulinaLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Moringa oleiferaFooDB
Murraya paniculataKNApSAcK Database
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Panax ginsengPlant
Phaseolus vulgarisLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Photinia melanocarpaLOTUS Database
Poa huecuLOTUS Database
Primula verisLOTUS Database
Prunus aviumPlant
Prunus dulcisFooDB
Prunus persicaFooDB
Ramalina fraxineaLOTUS Database
Saccharum officinarumLOTUS Database
Sassafras albidumLOTUS Database
Sebertia acuminataPlant
Siraitia grosvenoriiLOTUS Database
Streptomyces hainanensisLOTUS Database
Struthio camelusFooDB
Suaeda aegyptiacaLOTUS Database
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Swertia angustifoliaLOTUS Database
Tamarix aphyllaLOTUS Database
Telekia speciosaLOTUS Database
Thymus transcaucasicusLOTUS Database
Trevesia sundaicaLOTUS Database
Typha angustifoliaPlant
Vachellia tortuosaLOTUS Database
Virgilia oroboidesLOTUS Database
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
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
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point158 - 160 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility500 mg/mLNot Available
LogP-3.02Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility1220 g/LALOGPS
logP-2.6ALOGPS
logP-2.3ChemAxon
logS0.91ALOGPS
pKa (Strongest Acidic)11.31ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity29.96 m³·mol⁻¹ChemAxon
Polarizability13.37 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000646
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012306
KNApSAcK IDC00001113
Chemspider ID388821
KEGG Compound IDC02479
BioCyc IDBETA-L-ARABINOSE
BiGG IDNot Available
Wikipedia LinkArabinose
METLIN IDNot Available
PubChem Compound439764
PDB IDNot Available
ChEBI ID40886
Good Scents IDrw1006871
References
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Onkenhout W, Groener JE, Verhoeven NM, Yin C, Laan LA: L-Arabinosuria: a new defect in human pentose metabolism. Mol Genet Metab. 2002 Sep-Oct;77(1-2):80-5. [PubMed:12359133 ]
  3. Lobley RW, Burrows PC, Warwick R, Dawson DJ, Holmes R: Simultaneous assessment of intestinal permeability and lactose tolerance with orally administered raffinose, lactose and L-arabinose. Clin Sci (Lond). 1990 Aug;79(2):175-83. [PubMed:2167807 ]
  4. Osaki S, Kimura T, Sugimoto T, Hizukuri S, Iritani N: L-arabinose feeding prevents increases due to dietary sucrose in lipogenic enzymes and triacylglycerol levels in rats. J Nutr. 2001 Mar;131(3):796-9. [PubMed:11238761 ]
  5. Seri K, Sanai K, Matsuo N, Kawakubo K, Xue C, Inoue S: L-arabinose selectively inhibits intestinal sucrase in an uncompetitive manner and suppresses glycemic response after sucrose ingestion in animals. Metabolism. 1996 Nov;45(11):1368-74. [PubMed:8931641 ]
  6. Schutte JB, de Jong J, van Weerden EJ, Tamminga S: Nutritional implications of L-arabinose in pigs. Br J Nutr. 1992 Jul;68(1):195-207. [PubMed:1390604 ]
  7. Shaw W, Kassen E, Chaves E: Increased urinary excretion of analogs of Krebs cycle metabolites and arabinose in two brothers with autistic features. Clin Chem. 1995 Aug;41(8 Pt 1):1094-104. [PubMed:7628083 ]
  8. TOUSTER O, HARWELL SO: The isolation of L-arabitol from pentosuric urine. J Biol Chem. 1958 Feb;230(2):1031-41. [PubMed:13525419 ]
  9. Ahmed Z, Shimonishi T, Bhuiyan SH, Utamura M, Takada G, Izumori K: Biochemical preparation of L-ribose and L-arabinose from ribitol: a new approach. J Biosci Bioeng. 1999;88(4):444-8. doi: 10.1016/s1389-1723(99)80225-4. [PubMed:16232643 ]