MiMeDB: Showing metabocard for Tricycloalternarene 5b (MMDBc0008352)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 01:13:49 UTC

Update Date

2025-10-07 16:05:27 UTC

Metabolite ID

MMDBc0008352

Metabolite Identification

Common Name

Tricycloalternarene 5b

Description

Tricycloalternarene 5b is a member of the tricycloalternarene chemical class, identified as a metabolite in various biological contexts. This compound has garnered attention due to its significant inhibitory effects on biological targets, as demonstrated by its IC50 value of 18.6 ± 1.27 μM, indicating potent activity alongside other related compounds (PMID:37952710 ). Furthermore, it was isolated from the marine algae Laminaria japonica, where it was characterized alongside several known analogs, highlighting its relevance in natural product chemistry (PMID:30360544 ). The structural features of tricycloalternarene 5b suggest potential applications in drug discovery, particularly in the development of novel therapeutic agents. Its biological activity, combined with its unique chemical structure, positions tricycloalternarene 5b as a compound of interest for further exploration in both medicinal chemistry and biochemical research.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152103132D          

 26 28  0  0  0  0            999 V2000
   -3.6263   -0.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5644    0.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1536   -0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549    2.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604   -0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2673   -1.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -0.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8194   -0.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    0.5124    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  7  2  0  0  0  0
 15  3  1  0  0  0  0
 15  8  2  0  0  0  0
 16 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 13  1  0  0  0  0
 18 13  1  0  0  0  0
 18 16  1  0  0  0  0
 19  9  1  0  0  0  0
 19 17  2  0  0  0  0
 20 10  1  0  0  0  0
 21 17  1  0  0  0  0
 21 20  1  0  0  0  0
 22  4  1  0  0  0  0
 22 12  1  0  0  0  0
 22 18  1  0  0  0  0
 23 21  2  0  0  0  0
 24  5  1  0  0  0  0
 24 20  1  0  0  0  0
 25 19  1  0  0  0  0
 25 22  1  0  0  0  0
 26  8  1  0  0  0  0
M  END


  Mrv1652305152103132D          

 26 28  0  0  0  0            999 V2000
   -3.6263   -0.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5644    0.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1536   -0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549    2.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604   -0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2673   -1.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -0.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8194   -0.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    0.5124    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  7  2  0  0  0  0
 15  3  1  0  0  0  0
 15  8  2  0  0  0  0
 16 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 13  1  0  0  0  0
 18 13  1  0  0  0  0
 18 16  1  0  0  0  0
 19  9  1  0  0  0  0
 19 17  2  0  0  0  0
 20 10  1  0  0  0  0
 21 17  1  0  0  0  0
 21 20  1  0  0  0  0
 22  4  1  0  0  0  0
 22 12  1  0  0  0  0
 22 18  1  0  0  0  0
 23 21  2  0  0  0  0
 24  5  1  0  0  0  0
 24 20  1  0  0  0  0
 25 19  1  0  0  0  0
 25 22  1  0  0  0  0
 26  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0008352

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CC=C(C)C)=C(\C)C1CCC2(C)OC3=C(CC12)C(=O)C(CC3)OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O3/c1-14(2)7-6-8-15(3)16-11-12-22(4)18(16)13-17-19(25-22)9-10-20(24-5)21(17)23/h7-8,16,18,20H,6,9-13H2,1-5H3/b15-8+

> <INCHI_KEY>
DUKFNOHXGGAHSO-OVCLIPMQSA-N

> <FORMULA>
C22H32O3

> <MOLECULAR_WEIGHT>
344.495

> <EXACT_MASS>
344.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.81712004838636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11-methoxy-3-methyl-6-[(2E)-6-methylhepta-2,5-dien-2-yl]-2-oxatricyclo[7.4.0.0^{3,7}]tridec-1(9)-en-10-one

> <ALOGPS_LOGP>
4.88

> <JCHEM_LOGP>
4.3044003019999995

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.089587805091994

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
104.2093

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.40e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-methoxy-3-methyl-6-[(2E)-6-methylhepta-2,5-dien-2-yl]-2-oxatricyclo[7.4.0.0^{3,7}]tridec-1(9)-en-10-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      -6.769  -1.148   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.787   0.636   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.287  -1.012   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.036   5.144   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.199   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.726  -1.652   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.232  -1.973   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.250  -0.188   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.263  -0.828   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.744   0.132   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.198  -0.237   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.865   1.303   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.530   4.383   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0      -3.281   0.957   0.000  0.00  0.00           H+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   22                                                            
CONECT    5   24                                                            
CONECT    6    7    8                                                       
CONECT    7    6   14                                                       
CONECT    8    6   15   26                                                  
CONECT    9   10   19                                                       
CONECT   10    9   20                                                       
CONECT   11   12   16                                                       
CONECT   12   11   22                                                       
CONECT   13   17   18                                                       
CONECT   14    1    2    7                                                  
CONECT   15    3    8   16                                                  
CONECT   16   11   15   18                                                  
CONECT   17   13   19   21                                                  
CONECT   18   13   16   22                                                  
CONECT   19    9   17   25                                                  
CONECT   20   10   21   24                                                  
CONECT   21   17   20   23                                                  
CONECT   22    4   12   18   25                                             
CONECT   23   21                                                            
CONECT   24    5   20                                                       
CONECT   25   19   22                                                       
CONECT   26    8                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

Synonyms

Not Available

Molecular Formula

C₂₂H₃₂O₃

Average Mass

344.495

Monoisotopic Mass

344.23514489

IUPAC Name

11-methoxy-3-methyl-6-[(2E)-6-methylhepta-2,5-dien-2-yl]-2-oxatricyclo[7.4.0.0^{3,7}]tridec-1(9)-en-10-one

Traditional Name

11-methoxy-3-methyl-6-[(2E)-6-methylhepta-2,5-dien-2-yl]-2-oxatricyclo[7.4.0.0^{3,7}]tridec-1(9)-en-10-one

CAS Registry Number

Not Available

SMILES

[H]\C(CC=C(C)C)=C(\C)C1CCC2(C)OC3=C(CC12)C(=O)C(CC3)OC

InChI Identifier

InChI=1S/C22H32O3/c1-14(2)7-6-8-15(3)16-11-12-22(4)18(16)13-17-19(25-22)9-10-20(24-5)21(17)23/h7-8,16,18,20H,6,9-13H2,1-5H3/b15-8+

InChI Key

DUKFNOHXGGAHSO-OVCLIPMQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Cyclohexenone
Vinylogous ester
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0094 g/L	ALOGPS
logP	4.88	ALOGPS
logP	4.3	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.21 m³·mol⁻¹	ChemAxon
Polarizability	40.82 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

This table shows at most 5 pathways. For the full list of associated pathways:

See All Associated Bacterial Pathways

Name	SMPDB/PathBank	Species

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human supragingival plaque	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8720801

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10545410

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Tricycloalternarene 5b (MMDBc0008352)

MOL for #<Metabolite:0x00007f2ad4b6c7a8>

3D MOL for #<Metabolite:0x00007f2ad4b6c7a8>

3D SDF for #<Metabolite:0x00007f2ad4b6c7a8>

3D-SDF for #<Metabolite:0x00007f2ad4b6c7a8>

PDB for #<Metabolite:0x00007f2ad4b6c7a8>

3D PDB for #<Metabolite:0x00007f2ad4b6c7a8>

SMILES for #<Metabolite:0x00007f2ad4b6c7a8>

INCHI for #<Metabolite:0x00007f2ad4b6c7a8>

Structure for #<Metabolite:0x00007f2ad4b6c7a8>

3D Structure for #<Metabolite:0x00007f2ad4b6c7a8>