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Showing metabocard for L-Rhamnulose (HMDB0010207)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-15 09:55:03 UTC
Update Date2023-02-21 17:17:24 UTC
HMDB IDHMDB0010207
Secondary Accession Numbers
  • HMDB10207
Metabolite Identification
Common NameL-Rhamnulose
DescriptionL-Rhamnulose (CAS: 14807-05-7), also known as 6-deoxy-L-fructose, is a breakdown product of L-rhamnose, which is ubiquitous and particularly abundant in some plants, such as buckthorn. Rhamnose is also one of the sugars regularly used to conduct the dual sugar permeability test. Rhamnose is fermented by some colonic bacteria into L-rhamnulose. Three bacterial (gut microflora) enzymes are involved in rhamnose degradation including rhaB (rhamnulose kinase), rhaA (rhamnose isomerase), and rhaD (rhamnulose-1-phosphate aldolase). L-Rhamnulose kinase catalyzes the transfer of the gamma-phosphate group from ATP to the 1-hydroxyl group of L-rhamnulose. L-Rhamnulose has been found in Escherichia (PMID: 4975916 ).
Structure
Data?1676999844
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0010207 (L-Rhamnulose)


  Mrv1652309162004322D          

 11 11  0  0  0  0            999 V2000
10001.069310000.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.784510000.4782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.9846 9999.9464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.5567 9999.0274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7649 9999.0357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.225410000.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.678710000.9713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.011310000.4863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2662 9999.7017    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.0912 9999.7017    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.346110000.4863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  1 11  1  0  0  0  0
 11  3  1  1  0  0  0
 10  4  1  1  0  0  0
  9  5  1  6  0  0  0
  8  6  1  1  0  0  0
M  END
Download

3D MOL for HMDB0010207 (L-Rhamnulose)

HMDB0010207
     RDKit          3D
L-Rhamnulose
 23 23  0  0  0  0  0  0  0  0999 V2000
    2.0598    1.2710    1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9089    0.4080    0.6815 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1103    1.1441    0.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9929    0.1682   -0.3467 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8063    0.6263   -1.3924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9070   -0.1652    0.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5705    1.0251    1.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1880   -1.0000   -0.8290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2284   -1.0590   -2.2211 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2304   -0.5971   -0.4078 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9112   -1.7002    0.1002 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165    1.5678    2.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9941    2.2410    0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320    0.7841    0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5886   -0.1629    1.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5627   -0.0110   -1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4054   -0.5821    1.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7154   -0.8786    0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9108    1.4487    0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844   -1.9667   -0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1879   -0.2231   -2.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7334   -0.1364   -1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193   -2.2020   -0.6356 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  6
  4  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  1
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  1
  9 21  1  0
 10 22  1  6
 11 23  1  0
M  END
Download

3D SDF for HMDB0010207 (L-Rhamnulose)


  Mrv1652309162004322D          

 11 11  0  0  0  0            999 V2000
10001.069310000.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.784510000.4782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.9846 9999.9464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.5567 9999.0274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7649 9999.0357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.225410000.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.678710000.9713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.011310000.4863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2662 9999.7017    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.0912 9999.7017    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.346110000.4863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  1 11  1  0  0  0  0
 11  3  1  1  0  0  0
 10  4  1  1  0  0  0
  9  5  1  6  0  0  0
  8  6  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0010207

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O5/c1-3-4(8)5(9)6(10,2-7)11-3/h3-5,7-10H,2H2,1H3/t3-,4-,5+,6-/m1/s1

> <INCHI_KEY>
CJJCPDZKQKUXSS-ARQDHWQXSA-N

> <FORMULA>
C6H12O5

> <MOLECULAR_WEIGHT>
164.157

> <EXACT_MASS>
164.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
15.307711235285588

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.79

> <JCHEM_LOGP>
-1.7110893513333336

> <ALOGPS_LOGS>
0.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.770991544955194

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.286541504697956

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4509112110442075

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
34.8171

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R)-2-(hydroxymethyl)-5-methyloxolane-2,3,4-triol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0010207 (L-Rhamnulose)

HMDB0010207
     RDKit          3D
L-Rhamnulose
 23 23  0  0  0  0  0  0  0  0999 V2000
    2.0598    1.2710    1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9089    0.4080    0.6815 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1103    1.1441    0.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9929    0.1682   -0.3467 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8063    0.6263   -1.3924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9070   -0.1652    0.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5705    1.0251    1.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1880   -1.0000   -0.8290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2284   -1.0590   -2.2211 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2304   -0.5971   -0.4078 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9112   -1.7002    0.1002 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165    1.5678    2.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9941    2.2410    0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320    0.7841    0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5886   -0.1629    1.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5627   -0.0110   -1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4054   -0.5821    1.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7154   -0.8786    0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9108    1.4487    0.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844   -1.9667   -0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1879   -0.2231   -2.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7334   -0.1364   -1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193   -2.2020   -0.6356 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  6
  4  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  1
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  1
  9 21  1  0
 10 22  1  6
 11 23  1  0
M  END
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PDB for HMDB0010207 (L-Rhamnulose)

HEADER    PROTEIN                                 16-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.6638668.327   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8669.9988667.559   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8668.5058666.567   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8667.7068664.851   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8664.3618664.867   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8663.3548668.034   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8666.0678668.480   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8664.8218667.574   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.2978666.110   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.8378666.110   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.3138667.574   0.000  0.00  0.00           C+0
CONECT    1    2   11                                                       
CONECT    2    1                                                            
CONECT    3   11                                                            
CONECT    4   10                                                            
CONECT    5    9                                                            
CONECT    6    8                                                            
CONECT    7    8   11                                                       
CONECT    8    9    7    6                                                  
CONECT    9    8   10    5                                                  
CONECT   10    9   11    4                                                  
CONECT   11   10    7    1    3                                             
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0010207 (L-Rhamnulose)

COMPND    HMDB0010207
HETATM    1  C1  UNL     1       2.060   1.271   1.054  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.909   0.408   0.682  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.110   1.144   0.086  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.993   0.168  -0.347  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.806   0.626  -1.392  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.907  -0.165   0.803  1.00  0.00           C  
HETATM    7  O3  UNL     1      -2.570   1.025   1.139  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.188  -1.000  -0.829  1.00  0.00           C  
HETATM    9  O4  UNL     1      -0.228  -1.059  -2.221  1.00  0.00           O  
HETATM   10  C6  UNL     1       1.230  -0.597  -0.408  1.00  0.00           C  
HETATM   11  O5  UNL     1       1.911  -1.700   0.100  1.00  0.00           O  
HETATM   12  H1  UNL     1       1.917   1.568   2.135  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.994   2.241   0.496  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.032   0.784   0.971  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.589  -0.163   1.560  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.563  -0.011  -1.467  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.405  -0.582   1.672  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.715  -0.879   0.508  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.911   1.449   0.311  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.484  -1.967  -0.388  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.188  -0.223  -2.553  1.00  0.00           H  
HETATM   22  H11 UNL     1       1.733  -0.136  -1.275  1.00  0.00           H  
HETATM   23  H12 UNL     1       2.319  -2.202  -0.636  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   10   15
CONECT    3    4
CONECT    4    5    6    8
CONECT    5   16
CONECT    6    7   17   18
CONECT    7   19
CONECT    8    9   10   20
CONECT    9   21
CONECT   10   11   22
CONECT   11   23
END
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SMILES for HMDB0010207 (L-Rhamnulose)

C[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O
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INCHI for HMDB0010207 (L-Rhamnulose)

InChI=1S/C6H12O5/c1-3-4(8)5(9)6(10,2-7)11-3/h3-5,7-10H,2H2,1H3/t3-,4-,5+,6-/m1/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
6-Deoxy-L-arabino-hex-2-uloseHMDB
6-Deoxy-L-fructoseHMDB
6-Deoxy-beta-D-fructofuranoseHMDB
6-Deoxy-β-D-fructofuranoseHMDB
L-RhamnuloseHMDB
Chemical FormulaC6H12O5
Average Molecular Weight164.157
Monoisotopic Molecular Weight164.068473486
IUPAC Name(2R,3S,4S,5R)-2-(hydroxymethyl)-5-methyloxolane-2,3,4-triol
Traditional Name(2R,3S,4S,5R)-2-(hydroxymethyl)-5-methyloxolane-2,3,4-triol
CAS Registry Number470-21-3
SMILES
C[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H12O5/c1-3-4(8)5(9)6(10,2-7)11-3/h3-5,7-10H,2H2,1H3/t3-,4-,5+,6-/m1/s1
InChI KeyCJJCPDZKQKUXSS-ARQDHWQXSA-N
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
  • Oxolane
  • Secondary alcohol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility388 g/LALOGPS
logP-1.8ALOGPS
logP-1.7ChemAxon
logS0.85ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.82 m³·mol⁻¹ChemAxon
Polarizability15.31 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+135.14630932474
DeepCCS[M-H]-132.87730932474
DeepCCS[M-2H]-167.44530932474
DeepCCS[M+Na]+141.63330932474

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.03 minutes32390414
Predicted by Siyang on May 30, 202210.4701 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.95 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid195.6 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1115.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid332.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid41.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid182.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid65.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid283.2 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid256.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)253.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid654.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid61.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid976.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid193.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid214.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate560.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA292.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water301.6 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-RhamnuloseC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O3147.3Standard polar33892256
L-RhamnuloseC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O1466.0Standard non polar33892256
L-RhamnuloseC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O1446.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-Rhamnulose,1TMS,isomer #1C[C@H]1O[C@@](CO)(O[Si](C)(C)C)[C@@H](O)[C@@H]1O1510.6Semi standard non polar33892256
L-Rhamnulose,1TMS,isomer #2C[C@H]1O[C@](O)(CO[Si](C)(C)C)[C@@H](O)[C@@H]1O1457.6Semi standard non polar33892256
L-Rhamnulose,1TMS,isomer #3C[C@H]1O[C@](O)(CO)[C@@H](O[Si](C)(C)C)[C@@H]1O1486.6Semi standard non polar33892256
L-Rhamnulose,1TMS,isomer #4C[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O[Si](C)(C)C1480.6Semi standard non polar33892256
L-Rhamnulose,2TMS,isomer #1C[C@H]1O[C@@](CO[Si](C)(C)C)(O[Si](C)(C)C)[C@@H](O)[C@@H]1O1556.1Semi standard non polar33892256
L-Rhamnulose,2TMS,isomer #2C[C@H]1O[C@@](CO)(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O1553.9Semi standard non polar33892256
L-Rhamnulose,2TMS,isomer #3C[C@H]1O[C@@](CO)(O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C1573.0Semi standard non polar33892256
L-Rhamnulose,2TMS,isomer #4C[C@H]1O[C@](O)(CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O1543.0Semi standard non polar33892256
L-Rhamnulose,2TMS,isomer #5C[C@H]1O[C@](O)(CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C1550.1Semi standard non polar33892256
L-Rhamnulose,2TMS,isomer #6C[C@H]1O[C@](O)(CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C1540.8Semi standard non polar33892256
L-Rhamnulose,3TMS,isomer #1C[C@H]1O[C@@](CO[Si](C)(C)C)(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O1598.9Semi standard non polar33892256
L-Rhamnulose,3TMS,isomer #2C[C@H]1O[C@@](CO[Si](C)(C)C)(O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C1620.6Semi standard non polar33892256
L-Rhamnulose,3TMS,isomer #3C[C@H]1O[C@@](CO)(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C1599.2Semi standard non polar33892256
L-Rhamnulose,3TMS,isomer #4C[C@H]1O[C@](O)(CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C1588.2Semi standard non polar33892256
L-Rhamnulose,4TMS,isomer #1C[C@H]1O[C@@](CO[Si](C)(C)C)(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C1639.3Semi standard non polar33892256
L-Rhamnulose,1TBDMS,isomer #1C[C@H]1O[C@@](CO)(O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O1729.3Semi standard non polar33892256
L-Rhamnulose,1TBDMS,isomer #2C[C@H]1O[C@](O)(CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O1682.8Semi standard non polar33892256
L-Rhamnulose,1TBDMS,isomer #3C[C@H]1O[C@](O)(CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O1706.8Semi standard non polar33892256
L-Rhamnulose,1TBDMS,isomer #4C[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C1699.5Semi standard non polar33892256
L-Rhamnulose,2TBDMS,isomer #1C[C@H]1O[C@@](CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O1990.8Semi standard non polar33892256
L-Rhamnulose,2TBDMS,isomer #2C[C@H]1O[C@@](CO)(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2007.7Semi standard non polar33892256
L-Rhamnulose,2TBDMS,isomer #3C[C@H]1O[C@@](CO)(O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2018.8Semi standard non polar33892256
L-Rhamnulose,2TBDMS,isomer #4C[C@H]1O[C@](O)(CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O1999.1Semi standard non polar33892256
L-Rhamnulose,2TBDMS,isomer #5C[C@H]1O[C@](O)(CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C1996.5Semi standard non polar33892256
L-Rhamnulose,2TBDMS,isomer #6C[C@H]1O[C@](O)(CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2000.9Semi standard non polar33892256
L-Rhamnulose,3TBDMS,isomer #1C[C@H]1O[C@@](CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2275.9Semi standard non polar33892256
L-Rhamnulose,3TBDMS,isomer #2C[C@H]1O[C@@](CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2302.2Semi standard non polar33892256
L-Rhamnulose,3TBDMS,isomer #3C[C@H]1O[C@@](CO)(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2285.9Semi standard non polar33892256
L-Rhamnulose,3TBDMS,isomer #4C[C@H]1O[C@](O)(CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2290.0Semi standard non polar33892256
L-Rhamnulose,4TBDMS,isomer #1C[C@H]1O[C@@](CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2520.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - L-Rhamnulose GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Rhamnulose GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Rhamnulose 10V, Positive-QTOFsplash10-004i-0900000000-c557a6ada681319e43262021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Rhamnulose 20V, Positive-QTOFsplash10-00os-4900000000-7546c548a54ffc75a9882021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Rhamnulose 40V, Positive-QTOFsplash10-0a4j-9000000000-356d820473476bdd32b82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Rhamnulose 10V, Negative-QTOFsplash10-03di-4900000000-3eb1e9a5b306e08a73fc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Rhamnulose 20V, Negative-QTOFsplash10-052f-9300000000-cc1fa1d93325a6d9590f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Rhamnulose 40V, Negative-QTOFsplash10-0a4l-9000000000-e52bd33409aa2c7fd52f2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000437 +/- 0.000028 uMAdult (>18 years old)Not Specified
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027362
KNApSAcK IDC00019652
Chemspider ID10267875
KEGG Compound IDC00861
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15559441
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDRML
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Petrich K, Ludwig P, Kuhn H, Schewe T: The suppression of 5-lipoxygenation of arachidonic acid in human polymorphonuclear leucocytes by the 15-lipoxygenase product (15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid: structure-activity relationship and mechanism of action. Biochem J. 1996 Mar 15;314 ( Pt 3):911-6. [PubMed:8615788 ]
  2. Haviv F, Ratajczyk JD, DeNet RW, Martin YC, Dyer RD, Carter GW: Structural requirements for the inhibition of 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid analogues. J Med Chem. 1987 Feb;30(2):254-63. [PubMed:3806609 ]
  3. Chiu TH, Feingold DS: L-rhamnulose 1-phosphate aldolase from Escherichia coli. Crystallization and properties. Biochemistry. 1969 Jan;8(1):98-108. [PubMed:4975916 ]