NP-MRD: Showing NP-Card for D-Araboascorbic acid (NP0018502)

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Record Information

Version

2.0

Created at

2021-01-06 03:06:53 UTC

Updated at

2021-08-19 23:59:57 UTC

NP-MRD ID

NP0018502

Secondary Accession Numbers

None

Natural Product Identification

Common Name

D-Araboascorbic acid

Provided By

NPAtlas

Description

D-isoascorbic acid, also known as D-erythorbic acid or araboascorbate, belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. D-Araboascorbic acid is found in Flammulina velutipes, Penicillium sp. and Prunus avium . D-Araboascorbic acid was first documented in 2018 (PMID: 29428892). Based on a literature review a small amount of articles have been published on D-isoascorbic acid (PMID: 31873343) (PMID: 30855634).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242104353D          

 20 20  0  0  0  0            999 V2000
    2.3447    2.6434   -0.6281 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6888    1.5663   -0.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289    1.2494   -0.9300 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022   -0.0505   -0.5260 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1588   -0.0096    0.3175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4377   -1.3203    0.6903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2678    0.5519   -0.5358 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4890    0.5644    0.1177 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2620   -0.5262    0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3780   -1.7858    0.8171 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1883    0.4114    0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4463    0.3146    0.8878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349   -0.7410   -1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9905    0.5662    1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0877   -1.9528    0.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0110    1.5969   -0.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2855   -0.0377   -1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5640   -0.1237    0.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3313   -2.6386    0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1562   -0.2782    0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  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
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11  2  1  0  0  0  0
  4 13  1  6  0  0  0
  5 14  1  1  0  0  0
  6 15  1  0  0  0  0
  7 16  1  0  0  0  0
  7 17  1  0  0  0  0
  8 18  1  0  0  0  0
 10 19  1  0  0  0  0
 12 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0018502

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(O[H])[C@]([H])(OC1=O)[C@]([H])(O[H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5-/m1/s1

> <INCHI_KEY>
CIWBSHSKHKDKBQ-DUZGATOHSA-N

> <FORMULA>
C6H8O6

> <MOLECULAR_WEIGHT>
176.1241

> <EXACT_MASS>
176.032087988

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.920145577194909

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.58

> <JCHEM_LOGP>
-1.9135588756666668

> <ALOGPS_LOGS>
0.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.18187353605006

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.359916949362066

> <JCHEM_PKA_STRONGEST_BASIC>
-2.979728932431362

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
37.0321

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.45e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
erythorbic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0       2.345   2.643  -0.628  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.689   1.566  -0.474  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.429   1.249  -0.930  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.102  -0.051  -0.526  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.159  -0.010   0.318  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.438  -1.320   0.690  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.268   0.552  -0.536  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.489   0.564   0.118  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.262  -0.526   0.223  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.378  -1.786   0.817  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.188   0.411   0.256  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.446   0.315   0.888  0.00  0.00           O+0
HETATM   13  H   UNK     0      -0.035  -0.741  -1.401  0.00  0.00           H+0
HETATM   14  H   UNK     0      -0.991   0.566   1.237  0.00  0.00           H+0
HETATM   15  H   UNK     0      -1.088  -1.953   0.007  0.00  0.00           H+0
HETATM   16  H   UNK     0      -2.011   1.597  -0.811  0.00  0.00           H+0
HETATM   17  H   UNK     0      -2.285  -0.038  -1.477  0.00  0.00           H+0
HETATM   18  H   UNK     0      -3.564  -0.124   0.824  0.00  0.00           H+0
HETATM   19  H   UNK     0       1.331  -2.639   0.294  0.00  0.00           H+0
HETATM   20  H   UNK     0       4.156  -0.278   0.462  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9   13                                             
CONECT    5    4    6    7   14                                             
CONECT    6    5   15                                                       
CONECT    7    5    8   16   17                                             
CONECT    8    7   18                                                       
CONECT    9    4   10   11                                                  
CONECT   10    9   19                                                       
CONECT   11    9   12    2                                                  
CONECT   12   11   20                                                       
CONECT   13    4                                                            
CONECT   14    5                                                            
CONECT   15    6                                                            
CONECT   16    7                                                            
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19   10                                                            
CONECT   20   12                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Araboascorbic acid	ChEBI
D-Araboascorbic acid	ChEBI
D-Erythorbic acid	ChEBI
D-Erythro-hex-2-enonic acid gamma-lactone	ChEBI
Erythorbic acid	ChEBI
Isoascorbic acid	ChEBI
Isovitamin C	ChEBI
Araboascorbate	Generator
D-Araboascorbate	Generator
D-Erythorbate	Generator
D-Erythro-hex-2-enonate g-lactone	Generator
D-Erythro-hex-2-enonate gamma-lactone	Generator
D-Erythro-hex-2-enonate γ-lactone	Generator
D-Erythro-hex-2-enonic acid g-lactone	Generator
D-Erythro-hex-2-enonic acid γ-lactone	Generator
Erythorbate	Generator
Isoascorbate	Generator
D-Isoascorbate	Generator
Erythroascorbic acid	MeSH
Isoascorbic acid, monosodium salt	MeSH
Isoascorbic acid, disodium salt	MeSH
Isoascorbic acid, sodium salt	MeSH
Sodium erythorbate	MeSH

Chemical Formula

C₆H₈O₆

Average Mass

176.1241 Da

Monoisotopic Mass

176.03209 Da

IUPAC Name

(5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one

Traditional Name

erythorbic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5-/m1/s1

InChI Key

CIWBSHSKHKDKBQ-DUZGATOHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Flammulina velutipes	LOTUS Database	35616633
Penicillium sp.	NPAtlas	30061475
Prunus avium	Plant	KNApSAcK

Species Where Detected

Species Name	Source	Reference
Streptomyces microflavus No.2445	KNApSAcK Database	22123792

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
Enediol
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Primary alcohol
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

ascorbic acid (CHEBI:51438 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	164.00 to 171.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	552.00 to 553.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	400000 mg/L @ 25 °C (exp)	The Good Scents Company Information System
LogP	-2.779 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	-1.6	ALOGPS
logP	-1.9	ChemAxon
logS	0.14	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	37.03 m³·mol⁻¹	ChemAxon
Polarizability	14.92 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

NPAtlas ID

NPA007589

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00015725

Chemspider ID

16736142

KEGG Compound ID

C20364

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Erythorbic acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

51438

Good Scents ID

rw1019901

References

General References

Zhong S, Guan T, Xu Y, Zhou C, Shi L, Guo C, Zhou X, Li Z, He Y, Ji Y: Weak measurement-based sensor for the rapid identification of L(+)-ascorbic acid and D(-)-isoascorbic acid. Appl Opt. 2019 Nov 1;58(31):8583-8588. doi: 10.1364/AO.58.008583. [PubMed:31873343 ]
Gonda J, Fazekasova S, Martinkova M, Mitrikova T, Roman D, Pilatova MB: Synthesis and biological activity of sphingosines with integrated azobenzene switches. Org Biomol Chem. 2019 Mar 27;17(13):3361-3373. doi: 10.1039/c9ob00137a. [PubMed:30855634 ]
Zhao Y, Yuan H, Zhang X, Yang J: A stimuli-responsive fluorescence platform for simultaneous determination of d-isoascorbic acid and Tartaric acid based on Maillard reaction product. Spectrochim Acta A Mol Biomol Spectrosc. 2018 May 5;196:1-6. doi: 10.1016/j.saa.2018.01.079. Epub 2018 Feb 1. [PubMed:29428892 ]

Showing NP-Card for D-Araboascorbic acid (NP0018502)

MOL for NP0018502 (D-Araboascorbic acid)

3D MOL for NP0018502 (D-Araboascorbic acid)

3D SDF for NP0018502 (D-Araboascorbic acid)

3D-SDF for NP0018502 (D-Araboascorbic acid)

PDB for NP0018502 (D-Araboascorbic acid)

3D PDB for NP0018502 (D-Araboascorbic acid)

SMILES for NP0018502 (D-Araboascorbic acid)

INCHI for NP0018502 (D-Araboascorbic acid)

Structure for NP0018502 (D-Araboascorbic acid)

3D Structure for NP0018502 (D-Araboascorbic acid)