Showing metabocard for Saccharopine (BMDB0000279)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:27:45 UTC
Update Date2020-05-19 22:01:07 UTC
BMDB IDBMDB0000279
Secondary Accession Numbers
  • BMDB00279
Metabolite Identification
Common NameSaccharopine
DescriptionSaccharopinee belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Saccharopinee exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Saccharopinee exists in all living species, ranging from bacteria to humans. Saccharopinee participates in a number of enzymatic reactions, within cattle. In particular, Saccharopinee can be biosynthesized from L-lysine and oxoglutaric acid; which is catalyzed by the enzyme Alpha-aminoadipic semialdehyde synthase, mitochondrial. In addition, Saccharopinee can be converted into allysine and L-glutamic acid through the action of the enzyme Alpha-aminoadipic semialdehyde synthase, mitochondrial. In cattle, saccharopinee is involved in the metabolic pathway called the lysine degradation pathway. Saccharopinee is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
epsilon-N-(L-Glutar-2-yl)-L-lysineChEBI
N-[(S)-5-Amino-5-carboxypentyl]-L-glutamic acidChEBI
N6-(L-1,3-Dicarboxypropyl)-L-lysineChEBI
L-SaccharopineKegg
N-[(S)-5-Amino-5-carboxypentyl]-L-glutamateGenerator
(S)-N-(5-Amino-5-carboxypentyl)-L-glutamic acidHMDB
L-N-(5-Amino-5-carboxypentyl)-glutamic acidHMDB
L-SaccharopinHMDB
N(6)-(L-1,3-Dicarboxypropyl)-L-lysineHMDB
N-(5-Amino-5-carboxypentyl)-glutamic acidHMDB
N-(5-Amino-5-carboxypentyl)-L-glutamic acidHMDB
N-[(5S)-5-Amino-5-carboxypentyl]-L-glutamic acidHMDB
SaccharopinHMDB
Chemical FormulaC11H20N2O6
Average Molecular Weight276.2863
Monoisotopic Molecular Weight276.132136382
IUPAC Name(2S)-2-{[(5S)-5-amino-5-carboxypentyl]amino}pentanedioic acid
Traditional Namesaccharopine
CAS Registry Number997-68-2
SMILES
N[C@@H](CCCCN[C@@H](CCC(O)=O)C(O)=O)C(O)=O
InChI Identifier
InChI=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)/t7-,8-/m0/s1
InChI KeyZDGJAHTZVHVLOT-YUMQZZPRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Amino fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Secondary amine
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point247 - 250 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000279
DrugBank IDDB04207
Phenol Explorer Compound IDNot Available
FooDB IDFDB000461
KNApSAcK IDC00007227
Chemspider ID141086
KEGG Compound IDC00449
BioCyc IDSACCHAROPINE
BiGG ID1484994
Wikipedia LinkSaccharopine
METLIN ID383
PubChem Compound160556
PDB IDNot Available
ChEBI ID16927
References
Synthesis ReferenceBurkard, Ulrike; Walther, Ingrid; Effenberger, Franz. Amino acids. 6. Investigations on the synthesis of L-saccharopin. Liebigs Annalen der Chemie (1986), (6), 1030-43.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Alpha-aminoadipic semialdehyde synthase, mitochondrial
General function:
Amino acid transport and metabolism
Specific function:
Bifunctional enzyme that catalyzes the first two steps in lysine degradation. The N-terminal and the C-terminal contain lysine-oxoglutarate reductase and saccharopine dehydrogenase activity, respectively (By similarity).
Gene Name:
AASS
Uniprot ID:
A8E657
Molecular weight:
102084.0
Reactions
L-Lysine + NADPH + Oxoglutaric acid → Saccharopine + NADP + Waterdetails
Saccharopine + Water + NAD → Allysine + L-Glutamic acid + NADHdetails
Enzyme Details
2. Saccharopine dehydrogenase-like oxidoreductase
General function:
Involved in binding
Specific function:
N(6)-(L-1,3-dicarboxypropyl)-L-lysine + NAD(+) + H(2)O = L-glutamate + 2-aminoadipate 6-semialdehyde + NADH
Gene Name:
SCCPDH
Uniprot ID:
Q3T067
Molecular weight:
47320.0