(5S)-5-(carboxymethyl)-L-proline (CHEBI:45757)

ChEBI > Main

CHEBI:45757 - (5S)-5-(carboxymethyl)-L-proline

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	(5S)-5-(carboxymethyl)-L-proline

ChEBI ID	CHEBI:45757

ChEBI ASCII Name	(5S)-5-(carboxymethyl)-L-proline

Definition	A L-proline derivative that is L-proline substituted at position 5 by a carboxymethyl group.

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

Supplier Information	ChemicalBook:CB6395344, eMolecules:474394, ZINC000004658603

Download	Molfile XML SDF

more structures >>

Molfile

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__0730553898351984__ initializing

getValue debug = null

getValue logLevel = null

getValue allowjavascript = null

AppletRegistry.checkIn(jmolApplet0_object__0730553898351984__)

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%3ACHEBI%3A45757","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__0730553898351984__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"0730553898351984","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__0730553898351984__ 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 01071512013D

starting HoverWatcher_5

Time for openFile(

Mrv0541 01071512013D

23 23 0 0 0 0 999 V2000

0.1430 -0.4700 -0.1300 N 0 0 2 0 0 0 0 0 0 0 0 0

-0.3640 -0.5940 -1.5100 C 0 0 2 0 0 0 0 0 0 0 0 0

0.6540 -0.0570 -2.4820 C 0 0 0 0 0 0 0 0 0 0 0 0

1.4260 0.8040 -2.1340 O 0 0 0 0 0 0 0 0 0 0 0 0

0.7030 -0.5350 -3.7350 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.6620 0.2350 -1.5970 C 0 0 2 0 0 0 0 0 0 0 0 0

-2.1240 0.3180 -0.1190 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.7700 0.4110 0.6270 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.9190 -0.0850 2.0660 C 0 0 2 0 0 0 0 0 0 0 0 0

0.4160 -0.0210 2.7610 C 0 0 0 0 0 0 0 0 0 0 0 0

0.5260 -0.4100 4.0400 O 0 0 0 0 0 0 0 0 0 0 0 0

1.3880 0.3810 2.1660 O 0 0 0 0 0 0 0 0 0 0 0 0

1.3840 -0.3690 4.4860 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.2760 -1.1150 2.0590 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.6340 0.5430 2.5950 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4010 1.4370 0.6170 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0300 0.0070 -0.1890 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5760 -1.6390 -1.7360 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3570 -0.1900 -4.3590 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4070 -0.2760 -2.2060 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4570 1.2300 -1.9930 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.6680 -0.5810 0.1700 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7270 1.2090 0.0520 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 8 1 0 0 0 0

1 17 1 0 0 0 0

2 3 1 0 0 0 0

2 6 1 0 0 0 0

2 18 1 0 0 0 0

3 4 2 0 0 0 0

3 5 1 0 0 0 0

5 19 1 0 0 0 0

6 7 1 0 0 0 0

6 20 1 0 0 0 0

6 21 1 0 0 0 0

7 8 1 0 0 0 0

7 22 1 0 0 0 0

7 23 1 0 0 0 0

8 9 1 0 0 0 0

8 16 1 0 0 0 0

9 10 1 0 0 0 0

9 14 1 0 0 0 0

9 15 1 0 0 0 0

10 11 1 0 0 0 0

10 12 2 0 0 0 0

11 13 1 0 0 0 0

M END): 14 ms

reading 23 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

23 atoms created

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

Script completed

Jmol script terminated

Molfile expand

Formula

C7H11NO4

Net Charge

Average Mass

173.16650

Monoisotopic Mass

173.06881

InChI

InChI=1S/C7H11NO4/c9-6(10)3-4-1-2-5(8-4)7(11)12/h4-5,8H,1-3H2,(H,9,10)(H,11,12)/t4-,5-/m0/s1

InChIKey

LIZWYFXJOOUDNV-WHFBIAKZSA-N

SMILES

OC(=O)C[C@@H]1CC[C@H](N1)C(O)=O

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	(5S)-5-(carboxymethyl)-L-proline (CHEBI:45757) has role metabolite (CHEBI:25212) (5S)-5-(carboxymethyl)-L-proline (CHEBI:45757) is a L-proline derivative (CHEBI:84186) (5S)-5-(carboxymethyl)-L-proline (CHEBI:45757) is a dicarboxylic acid (CHEBI:35692) (5S)-5-(carboxymethyl)-L-proline (CHEBI:45757) is conjugate acid of (5S)-5-(carboxymethyl)-L-proline(1−) (CHEBI:73962)

Incoming	(5S)-5-(carboxymethyl)-L-proline(1−) (CHEBI:73962) is conjugate base of (5S)-5-(carboxymethyl)-L-proline (CHEBI:45757)

IUPAC Name

(5S)-5-(carboxymethyl)-L-proline

Synonym	Source
(2S,5S)-5-CARBOXYMETHYLPROLINE	PDBeChem

Manual Xrefs	Databases
C17366	KEGG COMPOUND
CPD-9369	MetaCyc
DB03215	DrugBank
SSC	PDBeChem
View more database links

Registry Number	Type	Source
8836822	Reaxys Registry Number	Reaxys

Citations

Batchelar ET, Hamed RB, Ducho C, Claridge TD, Edelmann MJ, Kessler B, Schofield CJ (2008)
Thioester hydrolysis and C-C bond formation by carboxymethylproline synthase from the crotonase superfamily.
Angewandte Chemie (International ed. in English) 47, 9322-9325 [PubMed:18972478]

Sleeman MC, Sorensen JL, Batchelar ET, McDonough MA, Schofield CJ (2005)
Structural and mechanistic studies on carboxymethylproline synthase (CarB), a unique member of the crotonase superfamily catalyzing the first step in carbapenem biosynthesis.
The Journal of biological chemistry 280, 34956-34965 [PubMed:16096274]
[show Abstract]

Last Modified

07 January 2015

CHEBI:45757 - (5S)-5-(carboxymethyl)-L-proline

ChEBI is part of the ELIXIR infrastructure