NP-MRD: Showing NP-Card for L-Gulonolactone (NP0001168)

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Record Information

Version

2.0

Created at

2006-08-12 21:33:03 UTC

Updated at

2024-09-17 15:44:16 UTC

NP-MRD ID

NP0001168

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-Gulonolactone

Description

L-Gulonolactone (also known as reduced ascorbic acid, RAA) is the substrate of the enzyme L-gulono-1,4-lactone oxidoreductase (EC 1.1.3.8), Which catalyzes the last step of the biosynthesis of L-ascorbic acid (vitamin C) in plants and animals. The enzyme L-Gulono-1,4-lactone oxidase is missing in scurvy-prone, vitamin C-deficient animals, such as humans. L-Gulonolactone is present in human blood and has been used as one of the markers to compare changes in exercise-induced oxidative stress. (PMID: 16956367 , 16494601 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1652309182018542D          

 13 13  0  0  0  0            999 V2000
10000.718610000.5377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.432810000.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.718610001.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.149210000.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.2108 9998.6765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4175 9998.6845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.880710000.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.6360 9999.5943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.331310000.6189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.663910000.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9188 9999.3493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.7438 9999.3493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.998710000.1339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  1  0  0  0
  2  4  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13  8  1  1  0  0  0
 12  5  1  6  0  0  0
 11  6  1  6  0  0  0
 10  7  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001168

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3+,4-,5+/m0/s1

> <INCHI_KEY>
SXZYCXMUPBBULW-SKNVOMKLSA-N

> <FORMULA>
C6H10O6

> <MOLECULAR_WEIGHT>
178.14

> <EXACT_MASS>
178.047738052

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
15.465415844188865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.05

> <JCHEM_LOGP>
-2.745273186

> <ALOGPS_LOGS>
0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.172871312116015

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.623539809865173

> <JCHEM_PKA_STRONGEST_BASIC>
-2.974938008499871

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
34.7788

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.37e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-gulonolactone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.0088667.670   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.3418666.900   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8668.0088669.212   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8670.6798667.670   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8667.0608664.196   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8663.7138664.211   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8662.7118667.377   0.000  0.00  0.00           O+0
HETATM    8  H   UNK     0    8667.8548665.909   0.000  0.00  0.00           H+0
HETATM    9  O   UNK     0    8665.4188667.822   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8664.1738666.917   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.6488665.452   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.1888665.452   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.6648666.917   0.000  0.00  0.00           C+0
CONECT    1    2    3   13                                                  
CONECT    2    1    4                                                       
CONECT    3    1                                                            
CONECT    4    2                                                            
CONECT    5   12                                                            
CONECT    6   11                                                            
CONECT    7   10                                                            
CONECT    8   13                                                            
CONECT    9   10   13                                                       
CONECT   10   11    9    7                                                  
CONECT   11   10   12    6                                                  
CONECT   12   11   13    5                                                  
CONECT   13   12    9    1    8                                             
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
gamma-Gulonolactone	ChEBI
L-Gulonic acid gamma-lactone	ChEBI
L-Gulono-gamma-lactone	ChEBI
g-Gulonolactone	Generator
Γ-gulonolactone	Generator
L-Gulonate g-lactone	Generator
L-Gulonate gamma-lactone	Generator
L-Gulonate γ-lactone	Generator
L-Gulonic acid g-lactone	Generator
L-Gulonic acid γ-lactone	Generator
L-Gulono-g-lactone	Generator
L-Gulono-γ-lactone	Generator
L-(+)-Gulono-1,4-lactone	HMDB
L-Gulono-1,4-lactone	HMDB
Reduced ascorbate	HMDB
Reduced ascorbic acid	HMDB
Gulonolactone, (L)-isomer	HMDB
Gulonolactone	HMDB
Gulonolactone, (D)-isomer	HMDB
Dihydroascorbic acid	HMDB
L-(+)-Gulonic acid gamma-lactone	HMDB
L-(+)-Gulonic acid γ-lactone	HMDB
L-Gulonolactone	HMDB

Chemical Formula

C₆H₁₀O₆

Average Mass

178.1400 Da

Monoisotopic Mass

178.04774 Da

IUPAC Name

(3S,4R,5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one

Traditional Name

L-gulonolactone

CAS Registry Number

1128-23-0

SMILES

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

InChI Identifier

InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3+,4-,5+/m0/s1

InChI Key

SXZYCXMUPBBULW-SKNVOMKLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

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	¹³C NMR Spectrum (1D, 252 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	¹³C NMR Spectrum (1D, 75 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	¹³C NMR Spectrum (1D, 126 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	¹³C NMR Spectrum (1D, 176 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	¹³C NMR Spectrum (1D, 226 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Arabidopsis thaliana	Plant	KNApSAcK
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Daucus carota	KNApSAcK Database	22123792
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Glycine max	Plant	KNApSAcK
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

gulonolactone (CHEBI:17587 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-2.571	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	637 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.7	ChemAxon
logS	0.55	ALOGPS
pKa (Strongest Acidic)	11.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	34.78 m³·mol⁻¹	ChemAxon
Polarizability	15.47 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

HMDB0003466

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

L-gulonolactone oxidase

METLIN ID

Not Available

PubChem Compound

439373

PDB ID

Not Available

ChEBI ID

17587

Good Scents ID

Not Available

References

General References

Wolucka BA, Communi D: Mycobacterium tuberculosis possesses a functional enzyme for the synthesis of vitamin C, L-gulono-1,4-lactone dehydrogenase. FEBS J. 2006 Oct;273(19):4435-45. Epub 2006 Sep 5. [PubMed:16956367 ]
Steinberg JG, Delliaux S, Jammes Y: Reliability of different blood indices to explore the oxidative stress in response to maximal cycling and static exercises. Clin Physiol Funct Imaging. 2006 Mar;26(2):106-12. [PubMed:16494601 ]
Zhu Y, Zhao J, Wang C, Zhang F, Huang X, Ren Z, Yang X, Liu Y, Yang X: Exploring the effectiveness of in ovo feeding of vitamin C based on the embryonic vitamin C synthesis and absorption in broiler chickens. J Anim Sci Biotechnol. 2021 Aug 3;12(1):86. doi: 10.1186/s40104-021-00607-w. [PubMed:34340712 ]
Shanaka KASN, Jung S, Janson ND, Jayasingha JRP, Madushani KP, Kim MJ, Lee J: Growth and Antioxidant-Related Effects of the Reestablished Ascorbic Acid Pathway in Zebrafish (Danio rerio) by Genomic Integration of L-Gulonolactone Oxidase From Cloudy Catshark (Scyliorhinus torazame). Front Physiol. 2021 Jul 5;12:685595. doi: 10.3389/fphys.2021.685595. eCollection 2021. [PubMed:34290620 ]
Hou M, Dai TM, Liang XY, Zhang SX, Cui WZ, Qiu JF, Sima YH, Cui WZ, Xu SQ: Bombyx mori can synthesize ascorbic acid through the l-gulose pathway to varying degrees depending on developmental stage. Arch Insect Biochem Physiol. 2021 Apr;106(4):e21783. doi: 10.1002/arch.21783. Epub 2021 Mar 15. [PubMed:33719082 ]
Boel A, Burger J, Vanhomwegen M, Beyens A, Renard M, Barnhoorn S, Casteleyn C, Reinhardt DP, Descamps B, Vanhove C, van der Pluijm I, Coucke P, Willaert A, Essers J, Callewaert B: Slc2a10 knock-out mice deficient in ascorbic acid synthesis recapitulate aspects of arterial tortuosity syndrome and display mitochondrial respiration defects. Hum Mol Genet. 2020 Jun 3;29(9):1476-1488. doi: 10.1093/hmg/ddaa071. [PubMed:32307537 ]
Paciolla C, Fortunato S, Dipierro N, Paradiso A, De Leonardis S, Mastropasqua L, de Pinto MC: Vitamin C in Plants: From Functions to Biofortification. Antioxidants (Basel). 2019 Oct 29;8(11). pii: antiox8110519. doi: 10.3390/antiox8110519. [PubMed:31671820 ]
Hasegawa T, Miyamoto-Takasaki Y, Abe M, Qiu Z, Yamamoto T, Yoshida T, Yoshino H, Hongo H, Yokoyama A, Sasaki M, Kuroshima S, Hara K, Kobayashi M, Akiyama Y, Maeda T, Luiz de Freitas PH, Li M, Amizuka N: Histochemical examination on principal collagen fibers in periodontal ligaments of ascorbic acid-deficient ODS-od/od rats. Microscopy (Oxf). 2019 Oct 9;68(5):349-358. doi: 10.1093/jmicro/dfz021. [PubMed:31271212 ]
Henriques SF, Duque P, Lopez-Fernandez H, Vazquez N, Fdez-Riverola F, Reboiro-Jato M, Vieira CP, Vieira J: Multiple independent L-gulonolactone oxidase (GULO) gene losses and vitamin C synthesis reacquisition events in non-Deuterostomian animal species. BMC Evol Biol. 2019 Jun 18;19(1):126. doi: 10.1186/s12862-019-1454-8. [PubMed:31215418 ]
Fu HY, Liu SL, Chiang YR: Biosynthesis of Ascorbic Acid as a Glucose-Induced Photoprotective Process in the Extremophilic Red Alga Galdieria partita. Front Microbiol. 2020 Jan 14;10:3005. doi: 10.3389/fmicb.2019.03005. eCollection 2019. [PubMed:31993036 ]
Wang X, Wei H, Mao X, Liu J: Proteomics Analysis of Lipid Droplets from the Oleaginous Alga Chromochloris zofingiensis Reveals Novel Proteins for Lipid Metabolism. Genomics Proteomics Bioinformatics. 2019 Jun;17(3):260-272. doi: 10.1016/j.gpb.2019.01.003. Epub 2019 Sep 5. [PubMed:31494267 ]

Showing NP-Card for L-Gulonolactone (NP0001168)

MOL for NP0001168 (L-Gulonolactone)

3D MOL for NP0001168 (L-Gulonolactone)

3D SDF for NP0001168 (L-Gulonolactone)

3D-SDF for NP0001168 (L-Gulonolactone)

PDB for NP0001168 (L-Gulonolactone)

3D PDB for NP0001168 (L-Gulonolactone)

SMILES for NP0001168 (L-Gulonolactone)

INCHI for NP0001168 (L-Gulonolactone)

Structure for NP0001168 (L-Gulonolactone)

3D Structure for NP0001168 (L-Gulonolactone)