<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4452</id>
  <title>T3D4398</title>
  <common-name>Saccharopine</common-name>
  <description>Saccharopine is an endogenous compound with the formula C11H20N2O6 and an average molecular weight of 276.29 g/mol. It exists as a solid at room temperature. Saccharopine belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds.

Biologically, saccharopine serves as a human metabolite and a metabolite of Saccharomyces cerevisiae. It is an intermediate in the degradation of lysine, formed by the condensation of lysine and alpha-ketoglutarate. In mammals, the saccharopine pathway is the primary route for lysine degradation. The first two reactions of this pathway are catalyzed by lysine-oxoglutarate reductase (LOR) and saccharopine dehydrogenase (SDH), which are located on a single bifunctional polypeptide (EC 1.5.1.8, LOR/SDH). This enzyme complex has been detected in the kidney and liver, and LOR activity has been observed in brain mitochondria during embryonic development. Saccharopine interacts with the mitochondrial alpha-aminoadipic semialdehyde synthase (AASS) protein target.</description>
  <cas>997-68-2</cas>
  <pubchem-id>160556</pubchem-id>
  <chemical-formula>C11H20N2O6</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>247 - 250°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity nil="true"/>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T06:50:55Z</created-at>
  <updated-at type="dateTime">2026-05-14T18:06:01Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Saccharopine</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C00449</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>16927</chebi-id>
  <biocyc-id>SACCHAROPINE</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB04207</drugbank-id>
  <pdb-id>SHR</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>N[C@@H](CCCCN[C@@H](CCC(O)=O)C(O)=O)C(O)=O</moldb-smiles>
  <moldb-formula>C11H20N2O6</moldb-formula>
  <moldb-inchi>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</moldb-inchi>
  <moldb-inchikey>ZDGJAHTZVHVLOT-YUMQZZPRSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">276.2863</moldb-average-mass>
  <moldb-mono-mass type="decimal">276.132136382</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Solid</state>
  <logp>-5.4</logp>
  <hmdb-id>HMDB00279</hmdb-id>
  <chembl-id nil="true"/>
  <chemspider-id>141086</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003358</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id nil="true"/>
  <iupac>(2S)-2-{[(5S)-5-amino-5-carboxypentyl]amino}pentanedioic acid</iupac>
  <moldb-polar-surface-area>149.95</moldb-polar-surface-area>
  <moldb-refractivity>63.95300000000001</moldb-refractivity>
  <moldb-polarizability>28.138708375547512</moldb-polarizability>
  <moldb-rotatable-bond-count>11</moldb-rotatable-bond-count>
  <moldb-acceptor-count>8</moldb-acceptor-count>
  <moldb-donor-count>5</moldb-donor-count>
  <moldb-pka-strongest-acidic>1.4444535649435268</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>10.892138404544818</moldb-pka-strongest-basic>
  <moldb-physiological-charge>-1</moldb-physiological-charge>
  <moldb-number-of-rings>0</moldb-number-of-rings>
  <moldb-alogps-logp>-2.77</moldb-alogps-logp>
  <moldb-alogps-logs>-1.72</moldb-alogps-logs>
  <moldb-alogps-solubility>5.25e+00 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organic acids and derivatives</superklass>
  <klass>Carboxylic acids and derivatives</klass>
  <subklass>Amino acids, peptides, and analogues</subklass>
  <paper-count type="integer">1558</paper-count>
  <sync-id>CED0007234</sync-id>
  <structure-inchikey>ZDGJAHTZVHVLOT-YUMQZZPRSA-N</structure-inchikey>
  <structure-fingerprint>40000000000000000000800000000000000000000000000000000000010000000000000000001000000000000000000004000008000000000000000000000000000000000000000000008000000000000020001000000000000000009000000000022000010000000000001000000000000000000000001000000000000000000000000000000000000000000000000080001000000000000000000000000000110000000000000000000000000000000000100000000000000000000000000000000008000000000000008000000000000000000000000000400000000000010000000000000840000000000000010400000000010000000000000000000000</structure-fingerprint>
  <structure-pattern-fingerprint>400000200102060088000000010820000000040000052000003000400200000c4002005000800000000001000080000004200084008c10010000643000a04000c4110400000004004080102000620100000000804000003240000422000009000c200002004002000000100054300000200080500105e0041118000002100002004400080c400008080002008808000811140012444014020004080000400080004300000010c00000000840016c211042c0020088010800100000100040020000000004044000020080020000410280000000000200400009000000080100000000081000000000004000000000200000100010804000200000000050400002</structure-pattern-fingerprint>
  <structure-pickle>ï¾­Þ������������������������€���`������ 4��������`�������`�������`�������`�������`������ 4��������`�������`�������(�������h��������(�������(�������h��������(�������(�������h��������(�������������������������������	�	
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  <structure-indexed-at type="dateTime">2026-09-19T04:01:16Z</structure-indexed-at>
</compound>
