Showing Compound Card for Saccharopine (CDB004835)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:41:41 UTC
Updated at2020-12-07 19:11:04 UTC
CannabisDB IDCDB004835
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameSaccharopine
DescriptionSaccharopine 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. The N(6)-(1,3-dicarboxypropan-1-yl) derivative of L-lysine. Saccharopine is a very strong basic compound (based on its pKa). Saccharopine exists in all living species, ranging from bacteria to humans. Within humans, saccharopine participates in a number of enzymatic reactions. In particular, saccharopine can be biosynthesized from L-lysine and oxoglutaric acid through the action of the enzyme Alpha-aminoadipic semialdehyde synthase, mitochondrial. In addition, saccharopine can be converted into allysine and L-glutamic acid through its interaction with the enzyme Alpha-aminoadipic semialdehyde synthase, mitochondrial. In humans, saccharopine is involved in the metabolic disorder called 2-aminoadipic 2-oxoadipic aciduria. Saccharopine is a potentially toxic compound. Saccharopine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight276.29
Monoisotopic Molecular Weight276.1321
IUPAC Name(2S)-2-{[(5S)-5-amino-5-carboxypentyl]amino}pentanedioic acid
Traditional Namesaccharopine
CAS Registry Number38495-82-8
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Physical Properties
StateNot Available
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSSaccharopine, non-derivatized, GC-MS Spectrumsplash10-0a4i-0923000000-1964addb7be546c2a45aSpectrum
GC-MSSaccharopine, non-derivatized, GC-MS Spectrumsplash10-0a4j-0913000000-49fae417f545c42253ddSpectrum
GC-MSSaccharopine, non-derivatized, GC-MS Spectrumsplash10-0a4i-0923000000-1964addb7be546c2a45aSpectrum
GC-MSSaccharopine, non-derivatized, GC-MS Spectrumsplash10-0a4j-0913000000-49fae417f545c42253ddSpectrum
Predicted GC-MSSaccharopine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001u-6950000000-fed481b3c49c1ab6ccd2Spectrum
Predicted GC-MSSaccharopine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9220800000-77f63e444994f915feaaSpectrum
Predicted GC-MSSaccharopine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSaccharopine, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-9240000000-d841eea4ebc5da1106f72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0290000000-c0b375ed0505ad2eab6c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0290000000-c0b375ed0505ad2eab6c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-9240000000-d841eea4ebc5da1106f72017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06ur-0190000000-34536967c85ac70477b52016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01qi-2790000000-ef0279e3d556894509f02016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-6900000000-76748510f1b49f459caf2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-417ff61b4b14d1bfe5fc2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01u9-1490000000-b4e2c5921f08ff4ee9772016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kms-7920000000-32382165ff3ba15b14d62016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0059-0190000000-b1accd72c8a2f16e7a712021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9310000000-56c681de611fbd62d1c72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-f91927cbf4969536ddce2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-dfdb3652043e0e0c5f802021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-1390000000-910bea675f309038db9a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f95-7900000000-1df925bebb97a29a80802021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Alpha-aminoadipic semialdehyde synthase, mitochondrialAASS7q31.3Q9UDR5 details
Probable saccharopine dehydrogenaseSCCPDH1q44Q8NBX0 details
Aminoadipate-semialdehyde synthaseAASS7q31.3A4D0W4 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000279
DrugBank IDDB04207
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000461
KNApSAcK IDC00007227
Chemspider ID141086
KEGG Compound IDC00449
BioCyc IDSACCHAROPINE
BiGG ID1484994
Wikipedia LinkSaccharopine
METLIN ID383
PubChem Compound160556
PDB IDNot Available
ChEBI ID16927
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Alpha-aminoadipic semialdehyde synthase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional enzyme that catalyzes the first two steps in lysine degradation. The N-terminal and the C-terminal contain lysine-ketoglutarate reductase and saccharopine dehydrogenase activity, respectively.
Gene Name:
AASS
Uniprot ID:
Q9UDR5
Molecular weight:
102130.895
Enzyme Details
2. Probable saccharopine dehydrogenase
General function:
Involved in catalytic activity
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:
Q8NBX0
Molecular weight:
47151.0
Enzyme Details
3. Aminoadipate-semialdehyde synthase
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AASS
Uniprot ID:
A4D0W4
Molecular weight:
102130.9