Record Information
Version1.0
Creation date2010-04-08 22:04:34 UTC
Update date2019-11-27 17:02:43 UTC
Primary IDFDB000461
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Saccharopine
DescriptionAmino acid from Saccharomyces cerevisiae and Neurospora crassaand is also found in mushrooms and seeds Saccharopine is an intermediate in the degradation of lysine, formed by condensation of lysine and alpha-ketoglutarate. The saccharopine pathway is the main route for lysine degradation in mammal and its first two reactions are catalyzed by enzymatic activities known as lysine-oxoglutarate reductase (LOR) and saccharopine dehydrogenase (SDH), which reside on a single bifunctional polypeptide (EC EC 1.5.1.8, LOR/SDH). The reactions involved by saccharopine dehydrogenases have a very strict substrate specificity for L-lysine, 2-oxoglutarate and NADPH. LOR/SDH has been detected in a number of mammalian tissues, mainly in the liver and kidney, contributing not only to the general nitrogen balance in the organism but also to the controlled conversion of lysine into ketone bodies. A tetrameric form has also been observed in human liver and placenta. LOR activity has also been detected in brain mitochondria during embryonic development, and this opens the question of whether the degradation of lysine has any functional significance during brain development and puts a new focus on the nutritional requirements for lysine in gestation and infancy. Finally, LOR and/or SDH deficiencies seem to be involved in a human autosomic genetic disorder known as familial hyperlysinemia, which is characterized by serious defects in the functioning of the nervous system, and characterized by deficiency in lysine-ketoglutarate reductase, saccharopine dehydrogenase, and saccharopine oxidoreductase activities. Saccharopinuria (high amounts of saccharopine in the urine) and saccharopinemia (an excess of saccharopine in the blood) are conditions present in some inherited disorders of lysine degradation. (PMID: 463877, 10567240, 10772957, 4809305); Saccharopine is an intermediate in the metabolism of amino acid lysine. It is a precursor of lysine in the alpha-aminoadipate pathway which occurs in a few lower fungi, the higher fungi, and euglenids. In mammals and higher plants saccharopine is an intermediate in the degradation of lysine, formed by condensation of lysine and alpha-ketoglutarate.
CAS Number997-68-2
Structure
Thumb
Synonyms
SynonymSource
(S)-N-(5-amino-5-carboxypentyl)-L-Glutamic acidbiospider
Epsilon-N-(L-Glutar-2-yl)-L-lysinebiospider
L-Glutamic acid, N-(5-amino-5-carboxypentyl)-, (S)-biospider
L-N-(5-amino-5-carboxypentyl)-Glutamic acidbiospider
L-saccharopinbiospider
L-saccharopinebiospider
N-(5-amino-5-carboxypentyl)-glutamic acidbiospider
N-(5-amino-5-carboxypentyl)-L-glutamic acidbiospider
N-(5-AMINO-5-CARBOXYPENTYL)GLUTAMIC ACIDbiospider
N-[(5S)-5-amino-5-carboxypentyl]-L-Glutamic acidbiospider
N-[(S)-5-amino-5-Carboxypentyl]-L-glutamateGenerator
N-[(S)-5-Amino-5-carboxypentyl]-L-glutamic acidbiospider
N(6)-(L-1,3-dicarboxypropyl)-L-lysinebiospider
N6-(L-1,3-Dicarboxypropyl)-L-lysinebiospider
Saccharopinbiospider
Saccharopinebiospider
Saccharopine; L-formdb_source
SHRbiospider
Predicted Properties
PropertyValueSource
Water Solubility5.25 g/LALOGPS
logP-2.8ALOGPS
logP-5.4ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.44ChemAxon
pKa (Strongest Basic)10.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area149.95 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity63.95 m³·mol⁻¹ChemAxon
Polarizability28.14 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC11H20N2O6
IUPAC name(2S)-2-{[(5S)-5-amino-5-carboxypentyl]amino}pentanedioic acid
InChI IdentifierInChI=1S/C11H20N2O6/c12-7(10(16)17)3-1-2-6-13-8(11(18)19)4-5-9(14)15/h7-8,13H,1-6,12H2,(H,14,15)(H,16,17)(H,18,19)
InChI KeyZDGJAHTZVHVLOT-UHFFFAOYSA-N
Isomeric SMILESNC(CCCCNC(CCC(O)=O)C(O)=O)C(O)=O
Average Molecular Weight276.2863
Monoisotopic Molecular Weight276.132136382
Classification
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Amino fatty acid
  • Fatty acyl
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 47.82%; H 7.30%; N 10.14%; O 34.74%DFC
Melting PointMp 257-259° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa5 10.3DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]23D +33.6 (c, 1 in 0.5N HCl) (c, 2.2 in 0.5N NaOH)DFC
Spectroscopic UV Data[neutral] lmax (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bu0-0190000000-fb104851b495a5b0fc12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qi-1690000000-17fa4d947a84b9fbcd33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-6910000000-10104d4d9601241c191fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-0190000000-d7592a25b74a5d3479e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bw9-0290000000-98f3caad16a2f34ed91eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06yd-7930000000-8685c81fb0d25b975d93View in MoNA
ChemSpider ID141086
ChEMBL IDNot Available
KEGG Compound IDC00449
Pubchem Compound ID160556
Pubchem Substance IDNot Available
ChEBI ID16927
Phenol-Explorer IDNot Available
DrugBank IDDB04207
HMDB IDHMDB00279
CRC / DFC (Dictionary of Food Compounds) IDBCP20-Z:BCP21-A
EAFUS IDNot Available
Dr. Duke IDSACCHAROPINE|L-SACCHAROPINE
BIGG ID1484994
KNApSAcK IDC00007227
HET IDSHR
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSaccharopine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Aminoadipate-semialdehyde synthaseAASSA4D0W4
Pathways
NameSMPDB LinkKEGG Link
Lysine DegradationSMP00037 map00310
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).