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Showing NP-Card for l-6-deoxyascorbic acid (NP0153417)

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Record Information
Version2.0
Created at2022-09-02 10:04:14 UTC
Updated at2022-09-02 10:04:14 UTC
NP-MRD IDNP0153417
Secondary Accession NumbersNone
Natural Product Identification
Common Namel-6-deoxyascorbic acid
Description6-Deoxy-L-ascorbic acid, also known as 6-deoxy-L-ascorbate, belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. l-6-deoxyascorbic acid is found in Flammulina velutipes. l-6-deoxyascorbic acid was first documented in 2004 (PMID: 15388172). Based on a literature review a small amount of articles have been published on 6-Deoxy-L-ascorbic acid (PMID: 26866456) (PMID: 15590689).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0153417 (l-6-deoxyascorbic acid)


  Mrv1652309022212042D          

 11 11  0  0  1  0            999 V2000
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for NP0153417 (l-6-deoxyascorbic acid)

     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.0171    0.4648   -0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3069   -0.6078   -0.2470 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2369   -1.2108    0.6227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1854   -0.1011    0.6212 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3573   -1.2253    1.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6911   -1.3115    1.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4821   -2.1970    1.4457 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0027   -0.1792    0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2968    0.0232   -0.3552 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9088    0.5189   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8600    1.6426   -0.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1005    0.2285   -1.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9098    1.4802   -0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6884    0.5165   -2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9607   -1.3765   -0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2459   -0.7116    1.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6403    0.5704    1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7779    0.9065   -0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9152    2.5694   -0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  6
  3 16  1  0
  4 17  1  1
  9 18  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0153417 (l-6-deoxyascorbic acid)


  Mrv1652309022212042D          

 11 11  0  0  1  0            999 V2000
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153417

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O5/c1-2(7)5-3(8)4(9)6(10)11-5/h2,5,7-9H,1H3/t2-,5+/m0/s1

> <INCHI_KEY>
LGBPWIAXPVUTMY-JLAZNSOCSA-N

> <FORMULA>
C6H8O5

> <MOLECULAR_WEIGHT>
160.125

> <EXACT_MASS>
160.037173358

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.884323341905878

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.09

> <JCHEM_LOGP>
-0.8666489089999999

> <ALOGPS_LOGS>
0.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.337120396236546

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.525256443265348

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0889489667055985

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
35.4884

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e+02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0153417 (l-6-deoxyascorbic acid)

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PDB for NP0153417 (l-6-deoxyascorbic acid)
HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.306   1.175   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0153417 (l-6-deoxyascorbic acid)
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SMILES for NP0153417 (l-6-deoxyascorbic acid)
C[C@H](O)[C@H]1OC(=O)C(O)=C1O
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INCHI for NP0153417 (l-6-deoxyascorbic acid)
InChI=1S/C6H8O5/c1-2(7)5-3(8)4(9)6(10)11-5/h2,5,7-9H,1H3/t2-,5+/m0/s1
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View in JSmol
Synonyms
ValueSource
6-Deoxy-L-ascorbateGenerator
Chemical FormulaC6H8O5
Average Mass160.1250 Da
Monoisotopic Mass160.03717 Da
IUPAC Name(5R)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]-2,5-dihydrofuran-2-one
Traditional Name(5R)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]-5H-furan-2-one
CAS Registry NumberNot Available
SMILES
C[C@H](O)[C@H]1OC(=O)C(O)=C1O
InChI Identifier
InChI=1S/C6H8O5/c1-2(7)5-3(8)4(9)6(10)11-5/h2,5,7-9H,1H3/t2-,5+/m0/s1
InChI KeyLGBPWIAXPVUTMY-JLAZNSOCSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Flammulina velutipesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDihydrofurans  
Sub ClassFuranones  
Direct ParentButenolides  
Alternative Parents
Substituents
  • 2-furanone
    • 

  • Vinylogous acid
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Enediol
    • 

  • Lactone
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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-1.1ALOGPS
logP-0.87ChemAxon
logS0.15ALOGPS
pKa (Strongest Acidic)4.53ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.49 m³·mol⁻¹ChemAxon
Polarizability13.88 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10398497  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54679898  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wang H, Xu R, Shi Y, Si L, Jiao P, Fan Z, Han X, Wu X, Zhou X, Yu F, Zhang Y, Zhang L, Zhang L, Zhou D, Xiao S: Design, synthesis and biological evaluation of novel L-ascorbic acid-conjugated pentacyclic triterpene derivatives as potential influenza virus entry inhibitors. Eur J Med Chem. 2016 Mar 3;110:376-88. doi: 10.1016/j.ejmech.2016.01.005. Epub  2016 Jan 8. [PubMed:26866456  ] 
  2. Corpe CP, Lee JH, Kwon O, Eck P, Narayanan J, Kirk KL, Levine M: 6-Bromo-6-deoxy-L-ascorbic acid: an ascorbate analog specific for Na+-dependent vitamin C transporter but not glucose transporter pathways. J Biol Chem. 2005 Feb 18;280(7):5211-20. doi: 10.1074/jbc.M412925200. Epub 2004  Dec 6. [PubMed:15590689  ] 
  3. Manfredini S, Vertuani S, Pavan B, Vitali F, Scaglianti M, Bortolotti F, Biondi C, Scatturin A, Prasad P, Dalpiaz A: Design, synthesis and in vitro evaluation on HRPE cells of ascorbic and 6-bromoascorbic acid conjugates with neuroactive molecules. Bioorg Med Chem. 2004 Oct 15;12(20):5453-63. doi: 10.1016/j.bmc.2004.07.043. [PubMed:15388172  ] 
  4. LOTUS database [Link]