NP-MRD: Showing NP-Card for Monodehydro-L-ascorbic acid (NP0339395)

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Record Information

Version

2.0

Created at

2024-09-11 21:37:19 UTC

Updated at

2024-09-11 21:37:20 UTC

NP-MRD ID

NP0339395

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Monodehydro-L-ascorbic acid

Description

It was first documented in 1998 (PMID: 9506998).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02271200462D          

 13 13  0  0  1  0            999 V2000
   10.3418  -12.6072    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   10.8267  -11.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5718  -11.1552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2394  -10.6703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9067  -11.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6913  -10.9003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6518  -11.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1366  -12.6073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7872  -10.9002    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1741  -11.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6157  -10.0932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3895  -11.1972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3582  -10.3583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  2  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  6  0  0  0
 10 12  1  0  0  0  0
  3 13  1  6  0  0  0
M  CHG  1   1  -1
M  END
> <DATABASE_ID>
NP0339395

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(OC(=O)C(O)=C1[O-])[C@@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/p-1/t2-,5+/m0/s1

> <INCHI_KEY>
CIWBSHSKHKDKBQ-JLAZNSOCSA-M

> <FORMULA>
C6H7O6

> <MOLECULAR_WEIGHT>
175.1162

> <EXACT_MASS>
175.024262956

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
14.517220199599274

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate

> <ALOGPS_LOGP>
-1.50

> <JCHEM_LOGP>
-1.9135588756666668

> <ALOGPS_LOGS>
0.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.197701448341192

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.359917442787388

> <JCHEM_PKA_STRONGEST_BASIC>
-2.979728932431362

> <JCHEM_POLAR_SURFACE_AREA>
110.05000000000001

> <JCHEM_REFRACTIVITY>
47.5824

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.51e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vitamin-C

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0      19.305 -23.533   0.000  0.00  0.00           O-1
HETATM    2  C   UNK     0      20.210 -22.288   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.734 -20.823   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      20.980 -19.918   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      22.226 -20.823   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      23.690 -20.347   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      21.750 -22.288   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      22.655 -23.534   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      18.269 -20.347   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.125 -21.377   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      17.949 -18.841   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      15.660 -20.901   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0      19.335 -19.335   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    9   13                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    2    5    8                                                  
CONECT    8    7                                                            
CONECT    9    3   10   11                                                  
CONECT   10    9   12                                                       
CONECT   11    9                                                            
CONECT   12   10                                                            
CONECT   13    3                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Value	Source
Ascorbate	ChEBI
L-Ascorbate(1-)	ChEBI
L-Ascorbic acid, ion(1-)	ChEBI
Vitamin C	ChEBI
Ascorbic acid	Generator
L-Ascorbic acid(1-)	Generator
L-Ascorbate, ion(1-)	Generator
Monodehydro-L-ascorbate	Generator

Chemical Formula

C₆H₇O₆

Average Mass

175.1162 Da

Monoisotopic Mass

175.02426 Da

IUPAC Name

(2R)-2-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate

Traditional Name

vitamin-C

CAS Registry Number

Not Available

SMILES

[H][C@@]1(OC(=O)C(O)=C1[O-])[C@@H](O)CO

InChI Identifier

InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/p-1/t2-,5+/m0/s1

InChI Key

CIWBSHSKHKDKBQ-JLAZNSOCSA-M

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Primary alcohol
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

ascorbate (CHEBI:38290 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-1.5	ALOGPS
logP	-1.9	ChemAxon
logS	0.53	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	110.05 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.58 m³·mol⁻¹	ChemAxon
Polarizability	14.52 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029242

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54679076

PDB ID

Not Available

ChEBI ID

38290

Good Scents ID

Not Available

References

General References

Shamsi FA, Partal A, Sady C, Glomb MA, Nagaraj RH: Immunological evidence for methylglyoxal-derived modifications in vivo. Determination of antigenic epitopes. J Biol Chem. 1998 Mar 20;273(12):6928-36. doi: 10.1074/jbc.273.12.6928. [PubMed:9506998 ]
Duconge J, Miranda-Massari JR, Gonzalez MJ, Jackson JA, Warnock W, Riordan NH: Pharmacokinetics of vitamin C: insights into the oral and intravenous administration of ascorbate. P R Health Sci J. 2008 Mar;27(1):7-19. [PubMed:18450228 ]
Chen Q, Espey MG, Sun AY, Pooput C, Kirk KL, Krishna MC, Khosh DB, Drisko J, Levine M: Pharmacologic doses of ascorbate act as a prooxidant and decrease growth of aggressive tumor xenografts in mice. Proc Natl Acad Sci U S A. 2008 Aug 12;105(32):11105-9. doi: 10.1073/pnas.0804226105. Epub 2008 Aug 4. [PubMed:18678913 ]
Harrison FE, May JM: Vitamin C function in the brain: vital role of the ascorbate transporter SVCT2. Free Radic Biol Med. 2009 Mar 15;46(6):719-30. doi: 10.1016/j.freeradbiomed.2008.12.018. Epub 2009 Jan 6. [PubMed:19162177 ]

Showing NP-Card for Monodehydro-L-ascorbic acid (NP0339395)

MOL for NP0339395 (Monodehydro-L-ascorbic acid)

3D MOL for NP0339395 (Monodehydro-L-ascorbic acid)

3D SDF for NP0339395 (Monodehydro-L-ascorbic acid)

3D-SDF for NP0339395 (Monodehydro-L-ascorbic acid)

PDB for NP0339395 (Monodehydro-L-ascorbic acid)

3D PDB for NP0339395 (Monodehydro-L-ascorbic acid)

SMILES for NP0339395 (Monodehydro-L-ascorbic acid)

INCHI for NP0339395 (Monodehydro-L-ascorbic acid)

Structure for NP0339395 (Monodehydro-L-ascorbic acid)

3D Structure for NP0339395 (Monodehydro-L-ascorbic acid)