L-saccharopine (CHEBI:16927)

ChEBI > Main

CHEBI:16927 - L-saccharopine

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

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:CB2376433, eMolecules:31267389, eMolecules:530483, ZINC000008214783

Download	Molfile XML SDF

more structures >>

call loadScript javascripts\jsmol\core\package.js

call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode

call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js

Jmol JavaScript applet jmolApplet0_object__726517870648449__ initializing

getValue debug = null

getValue logLevel = null

getValue allowjavascript = null

AppletRegistry.checkIn(jmolApplet0_object__726517870648449__)

call loadScript javascripts\jsmol\core\corestate.z.js

viewerOptions:

{ "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16927","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__726517870648449__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"726517870648449","bgcolor":"#000" }

Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $

java.vendor: j2s

java.version: 0.0

os.name: j2s

Access: ALL

memory: 0.0/0.0

processors available: 1

useCommandThread: false

appletId:jmolApplet0_object (signed)

starting HoverWatcher_1

getValue emulate = null

defaults = "Jmol"

getValue boxbgcolor = null

getValue bgcolor = #000

backgroundColor = "#000"

getValue ANIMFRAMECallback = null

getValue APPLETREADYCallback = Jmol._readyCallback

APPLETREADYCallback = "Jmol._readyCallback"

getValue ATOMMOVEDCallback = null

getValue CLICKCallback = null

getValue ECHOCallback = null

getValue ERRORCallback = null

getValue EVALCallback = null

getValue HOVERCallback = null

getValue LOADSTRUCTCallback = null

getValue MEASURECallback = null

getValue MESSAGECallback = null

getValue MINIMIZATIONCallback = null

getValue PICKCallback = null

getValue RESIZECallback = null

getValue SCRIPTCallback = null

getValue SYNCCallback = null

getValue STRUCTUREMODIFIEDCallback = null

getValue doTranslate = null

language=en_US

getValue popupMenu = null

getValue script = null

Jmol applet jmolApplet0_object__726517870648449__ ready

call loadScript javascripts\jsmol\core\corescript.z.js

call loadScript javascripts\jsmol\J\script\FileLoadThread.js

starting QueueThread0_2

script 1 started

starting HoverWatcher_3

starting HoverWatcher_4

The Resolver thinks Mol

Mrv0541 10031411283D

starting HoverWatcher_5

Time for openFile(

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

-0.1050 -1.5830 7.4160 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

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): 19 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
12-O-Tetradecanoylphorbol-13-acetate (TPA), also commonly known as tetradecanoylphorbol acetate, tetradecanoyl phorbol acetate, and phorbol 12-myristate 13-acetate (PMA) is a diester of phorbol. It is a potent tumor promoter often employed in biomedical research to activate the signal transduction enzyme protein kinase C (PKC). The effects of TPA on PKC result from its similarity to one of the natural activators of classic PKC isoforms, diacylglycerol. TPA is a small molecule drug. In ROS biology, superoxide was identified as the major reactive oxygen species induced by TPA/PMA but not by ionomycin in mouse macrophages. Thus, TPA/PMA has been routinely used as an inducer for endogenous superoxide production. TPA is also being studied as a drug in the treatment of hematologic cancer TPA has a specific use in cancer diagnostics as a B-cell specific mitogen in cytogenetic testing. Cells must be divided in a cytogenic test to view the chromosomes. TPA is used to stimulate division of B-cells during cytogenetic diagnosis of B-cell cancers such as chronic lymphocytic leukemia. TPA is also commonly used together with ionomycin to stimulate T-cell activation, proliferation, and cytokine production, and is used in protocols for intracellular staining of these cytokines. TPA induces KSHV reactivation in PEL cell cultures via stimulation of the mitogen-activated protein kinase (MAPK)/extracellular signal-regulated kinase (ERK) pathway. The pathway involves the activation of the early-immediate viral protein RTA that contributes to the activation of the lytic cycle. TPA was first found in the Croton plant, a shrub found in Southeast Asia, exposure to which provokes a poison ivy-like rash. It underwent a phase 1 clinical trial.
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	Types	Sources
22449979	PubMed citation	Europe PMC
22862918	PubMed citation	Europe PMC

Last Modified

26 May 2016

CHEBI:16927 - L-saccharopine

ChEBI is part of the ELIXIR infrastructure