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Record Information
Version	2.0
Creation Date	2012-05-31 14:27:57 -0600
Update Date	2015-09-17 15:41:56 -0600
Secondary Accession Numbers	ECMDB20109
Identification
Name:	7,8-Diaminononanoate
Description	7,8-diaminononanoate (or DAPA) is an intermediate in biotin biosynthesis. It is a substrate for Adenosylmethionine-8-amino-7-oxononanoate aminotransferase (or bioA). This enzyme 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). The reaction is S-adenosyl-L-methionine + 8-amino-7-oxononanoate = S-adenosyl-4-methylthio-2-oxobutanoate + 7,8-diaminononanoate. DAPA is a simple intercalator, much like the widely studied 9-aminoacridine. (PMID 16180206; 16984394)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa7b3bbd4> Close
Synonyms:	(7R,8S)-7,8-diaminononanoate (7R,8S)-7,8-diaminononanoic acid 7,8-Diamino-Nonanoate 7,8-Diamino-Nonanoic Acid 7,8-Diaminononanoate 7,8-Diaminononanoic acid 7,8-Diaminopelargonate 7,8-Diaminopelargonic acid 7,8DANA DAPA Diaminononanoate Diaminononanoic acid DNN
Chemical Formula:	C9H19N2O2
Weight:	Average: 187.264 Monoisotopic: 187.14520144
InChI Key:	KCEGBPIYGIWCDH-UHFFFAOYSA-M
InChI:	InChI=1S/C9H20N2O2/c1-7(10)8(11)5-3-2-4-6-9(12)13/h7-8H,2-6,10-11H2,1H3,(H,12,13)/p-1
CAS number:	21738-21-6
IUPAC Name:	7,8-diaminononanoic acid
Traditional IUPAC Name:	7,8-diaminopelargonic acid
SMILES:	CC(N)C(N)CCCCCC([O-])=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acids and conjugates
Direct Parent	Medium-chain fatty acids
Alternative Parents	Methyl-branched fatty acids Amino fatty acids Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
Substituents	Medium-chain fatty acid Amino fatty acid Branched fatty acid Methyl-branched fatty acid Amino acid or derivatives Amino acid Carboxylic acid derivative Carboxylic acid Monocarboxylic acid or derivatives Amine Organooxygen compound Organonitrogen compound Primary amine Primary aliphatic amine Hydrocarbon derivative Organic oxide Carbonyl group Organopnictogen compound Organic oxygen compound Organic nitrogen compound Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	amino fatty acid (CHEBI:2247 ) amino monocarboxylic acid (CHEBI:2247 )
Physical Properties
State:	Not Available
Charge:	1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 4.94 g/L ALOGPS logP -2.1 ALOGPS logP -1.9 ChemAxon logS -1.6 ALOGPS pKa (Strongest Acidic) 4.73 ChemAxon pKa (Strongest Basic) 9.97 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 89.34 Ų ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 51.3 m³·mol⁻¹ ChemAxon Polarizability 21.87 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-Diaminononanoate Adenosine triphosphate + Carbon dioxide + 7,8-Diaminononanoate <> ADP + Dethiobiotin +3 Hydrogen ion + Phosphate Adenosine triphosphate + 7,8-Diaminononanoate + Carbon dioxide <> ADP + Phosphate + Dethiobiotin S-Adenosylmethionine + 8-Amino-7-oxononanoate > S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-Diaminononanoate Carbon dioxide + 7,8-Diaminononanoate + Adenosine triphosphate > Hydrogen ion + Dethiobiotin + Phosphate + ADP S-adenosyl-L-methionine + 8-Amino-7-oxononanoate > S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-Diaminononanoate Adenosine triphosphate + 7,8-Diaminononanoate + Carbon dioxide > ADP + Inorganic phosphate + Dethiobiotin 8-Amino-7-oxononanoate + S-adenosyl-L-methionine > a sulfurated [sulfur carrier] + 7,8-Diaminononanoate + 7,8-Diaminononanoate 7,8-Diaminononanoate + Adenosine triphosphate + Carbon dioxide + 7,8-Diaminononanoate > Dethiobiotin + Adenosine diphosphate + Phosphate + ADP 8 8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate +7 7,8-Diaminononanoate Adenosine triphosphate + Carbon dioxide + 7 7,8-Diaminononanoate <> ADP + Dethiobiotin +3 Hydrogen ion + Phosphate 8 8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate +7 7,8-Diaminononanoate Adenosine triphosphate + Carbon dioxide + 7 7,8-Diaminononanoate <> ADP + Dethiobiotin +3 Hydrogen ion + Phosphate
SMPDB Pathways:	Biotin metabolism PW000762
KEGG Pathways:	Biotin metabolism ec00780 Metabolic pathways eco01100
EcoCyc Pathways:	biotin biosynthesis from 7-keto-8-aminopelargonate PWY0-1507
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-006x-9200000000-fd0faf23da0cbcd41210 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0fk9-0900000000-39e0da306191504f1d68 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0fmi-0900000000-a82a50cebd045c97de7a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-01t9-9800000000-c5d5b7d14b667632e6d9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000i-0900000000-b1acc9015cbd51ded6a6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00ku-1900000000-d93aaa190ec6fc69ae55 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4l-9600000000-c2b5f7eab5c98e05698b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00dr-0900000000-4b3f8bf19bc57391e0df View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0nba-8900000000-1f5731eeab1952ed8e86 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a5d-9200000000-b93fffc3d8ed727c4abc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000i-0900000000-d21a66b2d0094d0082ca View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-000l-1900000000-074fb3990cbfd1d68a3a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9300000000-e973f7f13c9147ebb191 View in MoNA 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:	Hoffmann, G. R., Yin, C. C., Terry, C. E., Ferguson, L. R., Denny, W. A. (2006). "Frameshift mutations induced by four isomeric nitroacridines and their des-nitro counterpart in the lacZ reversion assay in Escherichia coli." Environ Mol Mutagen 47:82-94. Pubmed: 16180206 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 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 2247 HMDB ID HMDB0304236 Pubchem Compound ID 652 Kegg ID C01037 ChemSpider ID 632 Wikipedia ID Not Available BioCyc ID DIAMINONONANOATE EcoCyc ID DIAMINONONANOATE

Enzymes