Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Showing metabocard for 5,6-Isopropylidene-L-ascorbic acid (HMDB0341280)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2022-09-09 20:08:21 UTC
Update Date2022-09-22 18:34:45 UTC
HMDB IDHMDB0341280
Secondary Accession NumbersNone
Metabolite Identification
Common Name5,6-Isopropylidene-L-ascorbic acid
Description5,6-Isopropylidene-L-ascorbic acid belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. Based on a literature review a small amount of articles have been published on 5,6-Isopropylidene-L-ascorbic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for HMDB0341280 (5,6-Isopropylidene-L-ascorbic acid)


  Mrv1652309092222462D          

 17 18  0  0  1  0            999 V2000
    0.5213   -0.6307    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -1.0052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9239   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689   -2.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439   -2.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9302   -3.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0370   -2.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890   -1.4901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -0.1802    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9915   -0.5548    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890    0.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    1.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    1.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689    1.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538    1.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239    0.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    0.0498    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  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  2  8  1  0  0  0  0
  2  9  1  6  0  0  0
  9 10  1  6  0  0  0
  9 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
Download

3D MOL for HMDB0341280 (5,6-Isopropylidene-L-ascorbic acid)

Download
3D SDF for HMDB0341280 (5,6-Isopropylidene-L-ascorbic acid)

  Mrv1652309092222462D          

 17 18  0  0  1  0            999 V2000
    0.5213   -0.6307    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -1.0052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9239   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689   -2.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439   -2.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9302   -3.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0370   -2.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890   -1.4901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -0.1802    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9915   -0.5548    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890    0.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    1.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    1.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689    1.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538    1.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239    0.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    0.0498    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  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  2  8  1  0  0  0  0
  2  9  1  6  0  0  0
  9 10  1  6  0  0  0
  9 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341280

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]1(COC(C)(C)O1)[C@@]1([H])OC(=O)C(O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C9H12O6/c1-9(2)13-3-4(15-9)7-5(10)6(11)8(12)14-7/h4,7,10-11H,3H2,1-2H3/t4-,7+/m0/s1

> <INCHI_KEY>
POXUQBFHDHCZAD-MHTLYPKNSA-N

> <FORMULA>
C9H12O6

> <MOLECULAR_WEIGHT>
216.189

> <EXACT_MASS>
216.063388106

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.116135183231936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxy-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
-0.21113426000000016

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.322027459234585

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.524571305608608

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4985562112139137

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
49.2391

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxy-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for HMDB0341280 (5,6-Isopropylidene-L-ascorbic acid)
Download
PDB for HMDB0341280 (5,6-Isopropylidene-L-ascorbic acid)
HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  H   UNK     0       0.973  -1.177   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       2.345  -1.876   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.591  -2.782   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.115  -4.246   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.575  -4.246   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.736  -5.778   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.069  -4.566   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.099  -2.782   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.345  -0.336   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0       3.717  -1.036   0.000  0.00  0.00           H+0
HETATM   11  O   UNK     0       1.099   0.569   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.575   2.033   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.670   3.279   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.115   2.033   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.021   3.279   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.591   0.569   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.056   0.093   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8    9                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    2                                                       
CONECT    9    2   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

Download
3D PDB for HMDB0341280 (5,6-Isopropylidene-L-ascorbic acid)
Download
SMILES for HMDB0341280 (5,6-Isopropylidene-L-ascorbic acid)
[H][C@]1(COC(C)(C)O1)[C@@]1([H])OC(=O)C(O)=C1O
Download
INCHI for HMDB0341280 (5,6-Isopropylidene-L-ascorbic acid)
InChI=1S/C9H12O6/c1-9(2)13-3-4(15-9)7-5(10)6(11)8(12)14-7/h4,7,10-11H,3H2,1-2H3/t4-,7+/m0/s1
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
5,6-Isopropylidene-L-ascorbateGenerator
Chemical FormulaC9H12O6
Average Molecular Weight216.189
Monoisotopic Molecular Weight216.063388106
IUPAC Name(5R)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
Traditional Name(5R)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxy-5H-furan-2-one
CAS Registry NumberNot Available
SMILES
[H][C@]1(COC(C)(C)O1)[C@@]1([H])OC(=O)C(O)=C1O
InChI Identifier
InChI=1S/C9H12O6/c1-9(2)13-3-4(15-9)7-5(10)6(11)8(12)14-7/h4,7,10-11H,3H2,1-2H3/t4-,7+/m0/s1
InChI KeyPOXUQBFHDHCZAD-MHTLYPKNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassEthers  
Direct ParentKetals  
Alternative Parents
Substituents
  • Ketal
    • 

  • 2-furanone
    • 

  • Meta-dioxolane
    • 

  • Dihydrofuran
    • 

  • Vinylogous acid
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Enediol
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
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
logP-0.21ChemAxon
pKa (Strongest Acidic)4.52ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.24 m³·mol⁻¹ChemAxon
Polarizability20.12 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties
Predicted Kovats Retention Indices
Not Available
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
    • 

  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation  details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation  details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10182353  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54691418  
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920  ]