MiMeDB: Showing metabocard for L-Gulono-1,4-lactone (MMDBc0033139)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:36:18 UTC

Update Date

2022-08-31 22:26:38 UTC

Metabolite ID

MMDBc0033139

Metabolite Identification

Common Name

L-Gulono-1,4-lactone

Description

L-Gulono-1,4-lactone, also known as L-gulonolactone, 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. L-Gulono-1,4-lactone exists in all living species, ranging from bacteria to plants to humans. L-Gulono-1,4-lactone has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make L-Gulono-1,4-lactone a potential biomarker for the consumption of these foods. L-Gulono-1,4-lactone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on L-Gulono-1,4-lactone.

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>
MMDBc0033139

> <DATABASE_NAME>
MIME

> <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

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	MeSH, HMDB
Gulonolactone	MeSH, HMDB
Gulonolactone, (D)-isomer	MeSH, HMDB
Dihydroascorbic acid	HMDB
L-(+)-Gulonic acid gamma-lactone	HMDB
L-(+)-Gulonic acid γ-lactone	HMDB
L-Gulonolactone	HMDB

Molecular Formula

C₆H₁₀O₆

Average Mass

178.14

Monoisotopic Mass

178.047738052

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

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0gc0-2961000000-10e3ffe56d1491c35d8a	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0gc0-2961000000-10e3ffe56d1491c35d8a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fr2-0930000000-725e277ca1152a7fbc98	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fr-9400000000-615dd94b06b3e5e78526	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0pk9-5359600000-e93f868058ca84374468	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-ec8c949182af76945e86	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-7a0472476f07853a992b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a70-9300000000-74777b41198e9cd46262	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-06ds-9000000000-2d40464867d71e6c1135	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01b9-9400000000-d5de17e2c0c42a02efc0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-0435329cc0eb001898fa	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-1900000000-f47818211aa007edc5f4	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-5900000000-c7c9eb2eaa1f91ac9951	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-072c615a4ace0aca930a	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00or-3900000000-5f8e27814cf4a835d41a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ar0-6900000000-9a9aef2bcc37f743beab	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-9100000000-4892df7d8d2a53c17d7f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9300000000-cd9f8103b846d70baac0	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-9000000000-650b3c2ec9303d9b2a96	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-232c502ee9a5b93d5a17	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03fu-1900000000-a9b5237063a8327d87cd	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0296-9500000000-aadb547d81673dce1915	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08mm-9100000000-0a3f8e5a08a10aa888eb	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Saliva

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0194740	Regucalcin	Unknown	Q15493	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001328	L-Gulonate	L-Gulono-1,4-lactone	Not Available	Gluconolactonase, Endoplasmic Reticulum	VMH	30371894
MMDBr0001333	L-Gulono-1,4-lactone	D-Glucurono-6,3-lactone	Not Available	Glucuronolactone Reductase	VMH	30371894
MMDBr0001395	L-Gulono-1,4-lactone	L-Gulono-1,4-lactone	Not Available	Gulonolactone Endoplasmic Reticular Transport	VMH	11458272
MMDBr0008398	L-Gulono-1,4-lactone	Hydrogen peroxide	Not Available	L-gulono-1,4-lactone oxidase (EC 1.1.3.8)	VMH	30371894
MMDBr0015145	L-Gulono-1,4-lactone	Hydrogen Ion	D-arabinono-1,4-lactone oxidase	Oxidation	RHEA	34755880
MMDBr0015146	L-Gulono-1,4-lactone	Hydrogen Ion	D-arabinono-1,4-lactone oxidase	Oxidation	RHEA	34755880
MMDBr0016287	Iron(3+)	Fe2+	L-gulono-1,4-lactone dehydrogenase	Dehydrogenation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Prostate cancer		Association	Human Blood	HMDB	19212411

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown
Bacteria	Firmicutes	11	Human ; Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	20	Human feces; Human	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB
Human Blood	Detected and Quantified	0.5	0.0	1.0	uM	Adult (>18 years old)	Both	Prostate Cancer	HMDB	19212411
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified					Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	24029555

External Links

HMDB ID

HMDB0003466

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1111/j.1475-097X.2006.00658.x. [PubMed:16494601 ]
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. doi: 10.1111/j.1742-4658.2006.05443.x. Epub 2006 Sep 5. [PubMed:16956367 ]

Showing metabocard for L-Gulono-1,4-lactone (MMDBc0033139)

MOL for #<Metabolite:0x00007fe27d522120>

3D MOL for #<Metabolite:0x00007fe27d522120>

3D SDF for #<Metabolite:0x00007fe27d522120>

3D-SDF for #<Metabolite:0x00007fe27d522120>

PDB for #<Metabolite:0x00007fe27d522120>

3D PDB for #<Metabolite:0x00007fe27d522120>

SMILES for #<Metabolite:0x00007fe27d522120>

INCHI for #<Metabolite:0x00007fe27d522120>

Structure for #<Metabolite:0x00007fe27d522120>

3D Structure for #<Metabolite:0x00007fe27d522120>