ECMDB: 8-Amino-7-oxononanoate (ECMDB20111) (M2MDB000959)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (476)

Record Information

Version

2.0

Creation Date

2012-05-31 14:28:04 -0600

Update Date

2015-06-03 17:19:20 -0600

Secondary Accession Numbers

ECMDB20111

Identification

Name:

8-Amino-7-oxononanoate

Description

8-amino-7-oxononanoate is a member of the chemical class known as Medium-chain Keto Acids and Derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. 8-amino-8-oxononanoic is involved in biotin biosynthesis. Diaminopelargonic acid aminotransferase (DAPA AT), which is involved in biotin biosynthesis, catalyzes the transamination of 8-amino-7-oxononanoic acid (KAPA) using S-adenosyl-L-methionine (AdoMet) as amino donor. (PMID 16984394)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(8S)-8-amino-7-oxononanoate
(8S)-8-amino-7-oxononanoic acid
7-KAP
7-Keto-8-aminopelargonate
7-Keto-8-aminopelargonic acid
7-Oxo-8-amino-nonanoate
7-Oxo-8-amino-nonanoic acid
8-amino-7-oxononanoate
8-Amino-7-oxononanoic acid
8A7ONA
KAP
KAPA

Chemical Formula:

C₉H₁₇NO₃

Weight:

Average: 187.2362
Monoisotopic: 187.120843415

InChI Key:

GUAHPAJOXVYFON-UHFFFAOYSA-N

InChI:

InChI=1S/C9H17NO3/c1-7(10)8(11)5-3-2-4-6-9(12)13/h7H,2-6,10H2,1H3,(H,12,13)

CAS number:

4707-58-8

IUPAC Name:

Not Available

Traditional IUPAC Name:

Not Available

SMILES:

CC(N)C(=O)CCCCCC(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

1,2-diols

Alternative Parents

Substituents

1,2-diol
Hydrocarbon derivative
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glycol (CHEBI:30742 )
ethanediol (CHEBI:30742 )
a glycol (GLYCOL )

Physical Properties

State:

Not Available

Charge:

Not Available

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	950 g/L	ALOGPS
logP	-1.5	ALOGPS
logS	1.18	ALOGPS
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Biotin metabolism

PW000762

KEGG Pathways:

Biotin metabolism ec00780
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120

EcoCyc Pathways:

7-keto-8-aminopelargonate biosynthesis I PWY-6519
biotin biosynthesis from 7-keto-8-aminopelargonate PWY0-1507

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-3f04f129d6a8c819d7bc	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-eaa1e5b7b88211fa7edb	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-dcef056f352184a24448	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-3f04f129d6a8c819d7bc	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-eaa1e5b7b88211fa7edb	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-dcef056f352184a24448	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-9000000000-7d7e99366b74aa908fb5	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9300000000-1cb14d2c8cf1747328eb	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-1d69e3daf74c74648262	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9000000000-7060d349c304512b9f75	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-3bc95e388ddb6eadd69d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-9000000000-c649f289b243e440bfa9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9000000000-7d8813644ca43096609f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ox-9000000000-17eed3caf789fe508145	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-9000000000-bc322895724fc86f7dc0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9000000000-8057e63671cfd392ae43	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-f589ce99213e8dfb1d61	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-8eeb88a032ec50107369	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-00ba25458eb6c0cc2940	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-00ba25458eb6c0cc2940	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-2fa6f85cb914a856ccc3	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Mann, S., Ploux, O. (2006). "7,8-Diaminoperlargonic acid aminotransferase from Mycobacterium tuberculosis, a potential therapeutic target. Characterization and inhibition studies." FEBS J 273:4778-4789. Pubmed: 16984394
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	12266
HMDB ID	HMDB0037790
Pubchem Compound ID	173
Kegg ID	C01092
ChemSpider ID	168
Wikipedia ID	Ethylene_Glycol
BioCyc ID	8-AMINO-7-OXONONANOATE
EcoCyc ID	8-AMINO-7-OXONONANOATE

Enzymes

Protein Details

1. Adenosylmethionine-8-amino-7-oxononanoate aminotransferase

General function:: Involved in transaminase activity
Specific function:: Catalyzes the transfer of the alpha-amino group from S- adenosyl-L-methionine (SAM) to 7-keto-8-aminopelargonic acid (KAPA) to form 7,8-diaminopelargonic acid (DAPA). It is the only animotransferase known to utilize SAM as an amino donor
Gene Name:: bioA
Uniprot ID:: P12995
Molecular weight:: 47335

Reactions

S-adenosyl-L-methionine + 8-amino-7-oxononanoate = S-adenosyl-4-methylthio-2-oxobutanoate + 7,8-diaminononanoate.

Protein Details

2. 8-amino-7-oxononanoate synthase

General function:: Involved in 8-amino-7-oxononanoate synthase activity
Specific function:: Catalyzes the decarboxylative condensation of pimeloyl- CoA and L-alanine to produce 8-amino-7-oxononanoate (AON), coenzyme A, and carbon dioxide
Gene Name:: bioF
Uniprot ID:: P12998
Molecular weight:: 41594

Reactions

6-carboxyhexanoyl-CoA + L-alanine = 8-amino-7-oxononanoate + CoA + CO(2).

8-Amino-7-oxononanoate (ECMDB20111) (M2MDB000959)

Structure for #<Compound:0xb2bb9c40>

Enzymes

Reactions

Reactions