Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 20:08:21 UTC

Update Date

2022-09-22 18:34:45 UTC

HMDB ID

HMDB0341280

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5,6-Isopropylidene-L-ascorbic acid

Description

5,6-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

MOL SDF PDB SMILES InChI


  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

$$$$

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,6-Isopropylidene-L-ascorbate	Generator

Chemical Formula

C₉H₁₂O₆

Average Molecular Weight

216.189

Monoisotopic Molecular Weight

216.063388106

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 Number

Not 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 Key

POXUQBFHDHCZAD-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.21	ChemAxon
pKa (Strongest Acidic)	4.52	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	49.24 m³·mol⁻¹	ChemAxon
Polarizability	20.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10182353

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54691418

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

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

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

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

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

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

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

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

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

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

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

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

Predicted Kovats Retention Indices