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Identification
YMDB IDYMDB00905
Name8-Amino-7-oxononanoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description8-Amino-7-oxononanoic acid (7-keto-8-aminopelargonate) is used as a substrate in biotin biosynthesis. Biotin is a water soluble, heterocyclic cofactor for a small number of enzymes that facilitate the transfer of CO2 during carboxylation, decarboxylation, and transcarboxylation reactions involved in fatty acid and carbohydrate metabolism. [Biocyc PWY0-1507]
Structure
Thumb
Synonyms
  • 8-Amino-7-oxononanoate
  • 8-Amino-7-oxononanoic acid
  • 1,2-Dihydroxyethane
  • 1,2-Ethanediol
  • 2-Hydroxyethanol
  • Ethanediol
  • Glycol
  • HO-CH2-CH2-OH
  • Monoethylene glycol
  • 1,2 Ethanediol
  • Glycol, monoethylene
  • 2 Hydroxyethanol
  • Glycol, ethylene
  • Poly(ethylene glycol)
  • Polyethylene oxide
  • Poly(ethylene oxide)
  • Polyoxyethylene
  • Poly(oxyethylene)
  • PEG
  • PEO
  • POE
  • Alkox
  • Carbowax
  • Carbowax sentry
  • Macrogol
  • MiraLax
  • Α,ω-hydroxypoly(ethylene oxide)
  • Α-hydro-ω-hydroxypoly(oxy-1,2-ethanediyl)
  • Α-hydro-ω-hydroxypoly(oxyethylene)
  • alpha,Omega-hydroxypoly(ethylene oxide)
  • alpha-Hydro-omega-hydroxypoly(oxy-1,2-ethanediyl)
  • alpha-Hydro-omega-hydroxypoly(oxyethylene)
  • Ethylene glycol homopolymer
  • Ethylene glycol polymer
  • Ethylene oxide polymer
  • Ethylene polyoxide
  • Ethylene glycol
  • Polyethylene glycol
CAS number4707-58-8
WeightAverage: 187.2362
Monoisotopic: 187.120843415
InChI KeyGUAHPAJOXVYFON-UHFFFAOYSA-N
InChIInChI=1S/C9H17NO3/c1-7(10)8(11)5-3-2-4-6-9(12)13/h7H,2-6,10H2,1H3,(H,12,13)
IUPAC NameNot Available
Traditional IUPAC NameNot Available
Chemical FormulaC9H17NO3
SMILES[H]OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(=O)C([H])(N([H])[H])C([H])([H])[H]
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct Parent1,2-diols
Alternative Parents
Substituents
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility950 g/LALOGPS
logP-1.5ALOGPS
logS1.18ALOGPS
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Biological Properties
Cellular Locations
  • Cell Envelope
  • Cytoplasm
  • Endoplasmic Reticulum
  • Extracellular
  • Lipid Particle
  • Mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
Biotin BiosynthesisPW002380 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Biotin metabolismec00780 Map00780
SMPDB Reactions
8-Amino-7-oxononanoic acid + S-Adenosyl-L-methionineDiaminopimelic acid + S-adenosyl-4-methylthio-2-oxobutanoate
KEGG Reactions
pimeloyl-CoA + L-Alaninehydron + 8-Amino-7-oxononanoic acid + Carbon dioxide + Coenzyme A
8-Amino-7-oxononanoic acid + S-AdenosylmethionineS-adenosyl-4-methylthio-2-oxobutanoic acid + 7,8-diaminononanoic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Phalip, V., Kuhn, I., Lemoine, Y., Jeltsch, J. M. (1999). "Characterization of the biotin biosynthesis pathway in Saccharomyces cerevisiae and evidence for a cluster containing BIO5, a novel gene involved in vitamer uptake." Gene 232:43-51.10333520
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15830
HMDB IDHMDB0037790
Pubchem Compound ID173
Kegg IDC01092
ChemSpider ID168
FOODB IDFDB009384
Wikipedia IDEthylene_Glycol
BioCyc IDNot Available

Enzymes

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:
BIO3
Uniprot ID:
P50277
Molecular weight:
53708.39844
Reactions
S-adenosyl-L-methionine + 8-amino-7-oxononanoate → S-adenosyl-4-methylthio-2-oxobutanoate + 7,8-diaminononanoate.

Transporters

General function:
Involved in amino acid transmembrane transporter activity
Specific function:
Transport into the cell of 7-keto 8-aminopelargonic acid
Gene Name:
BIO5
Uniprot ID:
P53744
Molecular weight:
62427.5