Record Information
Version2.0
Creation Date2012-05-31 14:27:57 -0600
Update Date2015-09-17 15:41:56 -0600
Secondary Accession Numbers
  • ECMDB20109
Identification
Name:7,8-Diaminononanoate
Description7,8-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
Thumb
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.94 g/LALOGPS
logP-2.1ALOGPS
logP-1.9ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)4.73ChemAxon
pKa (Strongest Basic)9.97ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area89.34 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity51.3 m³·mol⁻¹ChemAxon
Polarizability21.87 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Biotin metabolismPW000762 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • biotin biosynthesis from 7-keto-8-aminopelargonate PWY0-1507
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9200000000-fd0faf23da0cbcd41210View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0900000000-39e0da306191504f1d68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fmi-0900000000-a82a50cebd045c97de7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01t9-9800000000-c5d5b7d14b667632e6d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-b1acc9015cbd51ded6a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-1900000000-d93aaa190ec6fc69ae55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9600000000-c2b5f7eab5c98e05698bView in MoNA
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
External Links:
ResourceLink
CHEBI ID2247
HMDB IDNot Available
Pubchem Compound ID652
Kegg IDC01037
ChemSpider ID632
Wikipedia IDNot Available
BioCyc IDDIAMINONONANOATE
EcoCyc IDDIAMINONONANOATE

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
ATP + 7,8-diaminononanoate + CO(2) = ADP + phosphate + dethiobiotin
Gene Name:
ynfK
Uniprot ID:
P0A6E9
Molecular weight:
24981
Reactions
ATP + 7,8-diaminononanoate + CO(2) = ADP + phosphate + dethiobiotin.
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.
General function:
Involved in magnesium ion binding
Specific function:
ATP + 7,8-diaminononanoate + CO(2) = ADP + phosphate + dethiobiotin
Gene Name:
bioD
Uniprot ID:
P13000
Molecular weight:
24139
Reactions
ATP + 7,8-diaminononanoate + CO(2) = ADP + phosphate + dethiobiotin.