MiMeDB: Showing metabocard for 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:1) (MMDBc0031533)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:38:04 UTC

Update Date

2022-08-31 18:12:51 UTC

Metabolite ID

MMDBc0031533

Metabolite Identification

Common Name

1-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:1)

Description

1-Acyl-sn-glycero-3-phosphoethanolamine (n-C14:1) belongs to the class of Lysophosphatidylethanolamines. These are glycerophosphoetahnolamines (molecules containing an ethanolamine moiety attached to the phosphate group linked to a glycerol) with one saturated fatty acid bonded to the glycerol moiety through an ester linkage. (inferred from compound structure)

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08141218032D          

 30 29  0  0  0  0            999 V2000
   -2.0033   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7151   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4296   -2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283   -1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849   -3.3809    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   11.1592   -3.2704    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   11.9842   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717   -2.5559    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836   -1.3184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980   -3.3809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 15 14  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  2  0  0  0  0
 25 16  1  0  0  0  0
 25 19  1  0  0  0  0
 26 15  1  0  0  0  0
 27 17  1  0  0  0  0
 28 23  1  0  0  0  0
 28 24  2  0  0  0  0
 28 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29  7  1  0  0  0  0
 30  8  1  0  0  0  0
M  CHG  2  22   1  23  -1
M  RAD  2  20   3  22   2
M  END


  Mrv0541 08141218032D          

 30 29  0  0  0  0            999 V2000
   -2.0033   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7151   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4296   -2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283   -1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849   -3.3809    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   11.1592   -3.2704    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   11.9842   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717   -2.5559    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836   -1.3184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980   -3.3809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 15 14  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  2  0  0  0  0
 25 16  1  0  0  0  0
 25 19  1  0  0  0  0
 26 15  1  0  0  0  0
 27 17  1  0  0  0  0
 28 23  1  0  0  0  0
 28 24  2  0  0  0  0
 28 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29  7  1  0  0  0  0
 30  8  1  0  0  0  0
M  CHG  2  22   1  23  -1
M  RAD  2  20   3  22   2
M  END
> <DATABASE_ID>
MMDBc0031533

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCCCCC)=C(\[H])CCCCCC(=[O+])OCC(O)COP([O-])(=O)OCC[N]

> <INCHI_IDENTIFIER>
InChI=1S/C19H36NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-19(22)25-16-18(21)17-27-28(23,24)26-15-14-20/h7-8,18,21H,2-6,9-17H2,1H3,(H,23,24)/q+1/p-1/b8-7+

> <INCHI_KEY>
OYQMBAUDNLREGY-BQYQJAHWSA-M

> <FORMULA>
C19H35NO7P

> <MOLECULAR_WEIGHT>
420.4575

> <EXACT_MASS>
420.215113991

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
46.28077468626613

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{2-[(2-hydroxy-3-{[(7E)-1-(λ³-oxidanyliumylidene)tetradec-7-en-1-yl]oxy}propyl phosphonato)oxy]ethyl}azanylidene

> <ALOGPS_LOGP>
4.00

> <JCHEM_LOGP>
2.4037946781875563

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.34852261895492

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8871345027375703

> <JCHEM_PKA_STRONGEST_BASIC>
-3.538319999029481

> <JCHEM_POLAR_SURFACE_AREA>
105.12000000000002

> <JCHEM_REFRACTIVITY>
106.68329999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{2-[(2-hydroxy-3-{[(7E)-1-(λ³-oxidanyliumylidene)tetradec-7-en-1-yl]oxy}propyl phosphonato)oxy]ethyl}azanylidene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+1
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   28  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   29  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   29                                                  
CONECT    8    7    9   30                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   19                                                       
CONECT   14   15   20                                                       
CONECT   15   14   26                                                       
CONECT   16   18   25                                                       
CONECT   17   18   27                                                       
CONECT   18   16   17   21                                                  
CONECT   19   13   22   25                                                  
CONECT   20   14                                                            
CONECT   21   18                                                            
CONECT   22   19                                                            
CONECT   23   28                                                            
CONECT   24   28                                                            
CONECT   25   16   19                                                       
CONECT   26   15   28                                                       
CONECT   27   17   28                                                       
CONECT   28   23   24   26   27                                             
CONECT   29    7                                                            
CONECT   30    8                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   58    0
END

Synonyms

Not Available

Molecular Formula

C₁₉H₃₅NO₇P

Average Mass

420.4575

Monoisotopic Mass

420.215113991

IUPAC Name

{2-[(2-hydroxy-3-{[(7E)-1-(λ³-oxidanyliumylidene)tetradec-7-en-1-yl]oxy}propyl phosphonato)oxy]ethyl}azanylidene

Traditional Name

{2-[(2-hydroxy-3-{[(7E)-1-(λ³-oxidanyliumylidene)tetradec-7-en-1-yl]oxy}propyl phosphonato)oxy]ethyl}azanylidene

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCC)=C(\[H])CCCCCC(=[O+])OCC(O)COP([O-])(=O)OCC[N]

InChI Identifier

InChI=1S/C19H36NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-19(22)25-16-18(21)17-27-28(23,24)26-15-14-20/h7-8,18,21H,2-6,9-17H2,1H3,(H,23,24)/q+1/p-1/b8-7+

InChI Key

OYQMBAUDNLREGY-BQYQJAHWSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycerophospholipids. These are derivatives of glycerophosphoric acid that contains at least one O-acyl, or O-alkyl, or O-(1-alkenyl) group attached to the glycerol residue.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Not Available

Direct Parent

Glycerophospholipids

Alternative Parents

Substituents

Glycerophospholipid
Dialkyl phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Secondary alcohol
Carboxylic acid ester
Organic nitrene
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.063 g/L	ALOGPS
logP	4	ALOGPS
logP	2.4	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.12 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	106.68 m³·mol⁻¹	ChemAxon
Polarizability	46.28 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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

Metabolic Reactions

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
Bacteria	Proteobacteria	7	Human feces; Human sputum; Human ; Human unknown; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	244	Human feces; Human pleural fluid plaque; Human ; Human stool; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	122	Human feces; Human sputum; Human ; Human unknown; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	12	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	97	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	20	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	4	Human feces; Human	Metabolic reconstruction
Bacteria	Firmicutes	21	Human feces; Human pleural fluid plaque; Human ; Human stool; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	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
Human Feces	Detected but not Quantified									HMDB

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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:1) (MMDBc0031533)

MOL for #<Metabolite:0x00007f92507142a8>

3D MOL for #<Metabolite:0x00007f92507142a8>

3D SDF for #<Metabolite:0x00007f92507142a8>

3D-SDF for #<Metabolite:0x00007f92507142a8>

PDB for #<Metabolite:0x00007f92507142a8>

3D PDB for #<Metabolite:0x00007f92507142a8>

SMILES for #<Metabolite:0x00007f92507142a8>

INCHI for #<Metabolite:0x00007f92507142a8>

Structure for #<Metabolite:0x00007f92507142a8>

3D Structure for #<Metabolite:0x00007f92507142a8>