L-saccharopine (CHEBI:16927)

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CHEBI:16927 - L-saccharopine

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ChEBI Name	L-saccharopine

ChEBI ID	CHEBI:16927

ChEBI ASCII Name	L-saccharopine

Definition	The N⁶-(1,3-dicarboxypropan-1-yl) derivative of L-lysine.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:45721, CHEBI:7406, CHEBI:12660, CHEBI:21861

Supplier Information	ChemicalBook:CB1183283, eMolecules:30069636, ZINC000001532666

Download	Molfile XML SDF

more structures >>

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Mrv0541 10031411283D

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Mrv0541 10031411283D

39 38 0 0 0 0 999 V2000

0.7800 1.7080 4.6510 N 0 0 1 0 0 0 0 0 0 0 0 0

-0.0140 0.4790 4.7740 C 0 0 1 0 0 0 0 0 0 0 0 0

0.1570 -0.3670 3.5110 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.3190 0.4270 2.2950 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.1470 -0.4190 1.0320 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.6240 0.3760 -0.1840 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.4590 -0.4360 -1.3960 N 0 0 1 0 0 0 0 0 0 0 0 0

0.4550 -0.3040 5.9720 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.4070 -1.0800 6.6470 O 0 0 0 0 0 0 0 0 0 0 0 0

1.6080 -0.2340 6.3260 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.9320 0.3800 -2.5210 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.1640 0.0000 -3.7880 C 0 0 1 0 0 0 0 0 0 0 0 0

1.3290 0.2450 -3.5720 C 0 0 1 0 0 0 0 0 0 0 0 0

2.0860 -0.1300 -4.8200 C 0 0 0 0 0 0 0 0 0 0 0 0

3.4210 0.0030 -4.8610 O 0 0 0 0 0 0 0 0 0 0 0 0

1.4900 -0.5520 -5.7830 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.4040 0.1380 -2.7330 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.9390 -1.0540 -2.4280 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.1030 1.0170 -3.1780 O 0 0 0 0 0 0 0 0 0 0 0 0

1.7410 1.4220 4.5380 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5040 2.1460 3.7840 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0660 0.7370 4.8980 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2090 -0.6250 3.3870 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4310 -1.2800 3.6030 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3710 0.6850 2.4190 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2700 1.3390 2.2030 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9040 -0.6770 0.9080 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.7360 -1.3310 1.1240 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.6760 0.6340 -0.0600 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0340 1.2880 -0.2750 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5330 -0.5630 -1.5270 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.7660 1.4350 -2.2990 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3310 -1.0540 -4.0100 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5160 0.6060 -4.6220 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4950 1.2990 -3.3500 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6810 -0.3610 -2.7370 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.8840 -1.2100 -2.5640 H 0 0 0 0 0 0 0 0 0 0 0 0

3.9060 -0.2380 -5.6620 H 0 0 0 0 0 0 0 0 0 0 0 0

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1 20 1 0 0 0 0

1 21 1 0 0 0 0

2 3 1 0 0 0 0

2 8 1 0 0 0 0

2 22 1 0 0 0 0

3 4 1 0 0 0 0

3 23 1 0 0 0 0

3 24 1 0 0 0 0

4 5 1 0 0 0 0

4 25 1 0 0 0 0

4 26 1 0 0 0 0

5 6 1 0 0 0 0

5 27 1 0 0 0 0

5 28 1 0 0 0 0

6 7 1 0 0 0 0

6 29 1 0 0 0 0

6 30 1 0 0 0 0

7 11 1 0 0 0 0

7 31 1 0 0 0 0

8 9 1 0 0 0 0

8 10 2 0 0 0 0

9 39 1 0 0 0 0

11 12 1 0 0 0 0

11 17 1 0 0 0 0

11 32 1 0 0 0 0

12 13 1 0 0 0 0

12 33 1 0 0 0 0

12 34 1 0 0 0 0

13 14 1 0 0 0 0

13 35 1 0 0 0 0

13 36 1 0 0 0 0

14 15 1 0 0 0 0

14 16 2 0 0 0 0

15 38 1 0 0 0 0

17 18 1 0 0 0 0

17 19 2 0 0 0 0

18 37 1 0 0 0 0

M END): 21 ms

reading 39 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

39 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
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 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.
Read full article at Wikipedia

Formula

C11H20N2O6

Net Charge

Average Mass

276.28630

Monoisotopic Mass

276.13214

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

InChIKey

ZDGJAHTZVHVLOT-YUMQZZPRSA-N

SMILES

N[C@@H](CCCCN[C@@H](CCC(O)=O)C(O)=O)C(O)=O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed

Roles Classification
Biological Role(s):	mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. (via opine )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	L-saccharopine (CHEBI:16927) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) L-saccharopine (CHEBI:16927) has role human metabolite (CHEBI:77746) L-saccharopine (CHEBI:16927) has role mouse metabolite (CHEBI:75771) L-saccharopine (CHEBI:16927) is a L-lysine derivative (CHEBI:25095) L-saccharopine (CHEBI:16927) is a amino acid opine (CHEBI:83229) L-saccharopine (CHEBI:16927) is conjugate acid of L-saccharopinate(1−) (CHEBI:57951)

Incoming	L-saccharopinate(1−) (CHEBI:57951) is conjugate base of L-saccharopine (CHEBI:16927)

IUPAC Name

N-[(5S)-5-amino-5-carboxypentyl]-L-glutamic acid

Synonyms	Sources
epsilon-N-(L-Glutar-2-yl)-L-lysine	ChemIDplus
L-Saccharopine	KEGG COMPOUND
N-[(S)-5-Amino-5-carboxypentyl]-L-glutamic acid	KEGG COMPOUND
N6-(L-1,3-Dicarboxypropyl)-L-lysine	KEGG COMPOUND
Saccharopine	KEGG COMPOUND

Manual Xrefs	Databases
C00007227	KNApSAcK
C00449	KEGG COMPOUND
HMDB0000279	HMDB
Saccharopine	Wikipedia
SACCHAROPINE	MetaCyc
SHR	PDBeChem
View more database links

Registry Numbers	Types	Sources
3063139	Reaxys Registry Number	Reaxys
997-68-2	CAS Registry Number	KEGG COMPOUND
997-68-2	CAS Registry Number	ChemIDplus

Citations

Serrano GC, Rezende e Silva Figueira T, Kiyota E, Zanata N, Arruda P (2012)
Lysine degradation through the saccharopine pathway in bacteria: LKR and SDH in bacteria and its relationship to the plant and animal enzymes.
FEBS letters 586, 905-911 [PubMed:22449979]
[show Abstract]

Mukherjee S, Dawe AL, Creamer R (2012)
Potential role for saccharopine reductase in swainsonine metabolism in endophytic fungus, Undifilum oxytropis.
Fungal biology 116, 902-909 [PubMed:22862918]
[show Abstract]

Last Modified

26 May 2016

CHEBI:16927 - L-saccharopine

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