S-adenosyl-L-homocysteine (CHEBI:16680)

ChEBI > Main

CHEBI:16680 - S-adenosyl-L-homocysteine

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	S-adenosyl-L-homocysteine

ChEBI ID	CHEBI:16680

ChEBI ASCII Name	S-adenosyl-L-homocysteine

Definition	An organic sulfide that is the S-adenosyl derivative of L-homocysteine.

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

Secondary ChEBI IDs	CHEBI:45495, CHEBI:8945, CHEBI:12741, CHEBI:12759, CHEBI:12761, CHEBI:22034

Supplier Information	ChemicalBook:CB4451354, eMolecules:474983, ZINC000004228232

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__7688188846451456__ initializing

getValue debug = null

getValue logLevel = null

getValue allowjavascript = null

AppletRegistry.checkIn(jmolApplet0_object__7688188846451456__)

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:16680","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__7688188846451456__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"7688188846451456","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__7688188846451456__ 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

Marvin 09040815393D

starting HoverWatcher_5

Time for openFile(

Marvin 09040815393D

46 48 0 0 0 0 999 V2000

-0.6558 -3.2780 -0.4862 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.9781 -2.7147 -1.0366 C 0 0 2 0 0 0 0 0 0 0 0 0

-2.4406 -1.7688 0.0881 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.2194 -1.1818 0.5326 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.1993 -2.1920 0.5200 C 0 0 2 0 0 0 0 0 0 0 0 0

-2.9508 -3.7109 -1.3364 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.8271 -4.5406 0.1573 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.3817 -0.7693 -0.3242 N 0 0 0 0 0 0 0 0 0 0 0 0

-3.1961 0.2269 -1.2115 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.6617 -0.6575 0.0940 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.4134 0.8949 -1.3470 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.1094 0.6145 -1.9299 N 0 0 0 0 0 0 0 0 0 0 0 0

-5.3117 0.3458 -0.5192 N 0 0 0 0 0 0 0 0 0 0 0 0

-4.5063 1.9437 -2.2776 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.2002 1.6555 -2.8013 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.3880 2.2980 -2.9671 N 0 0 0 0 0 0 0 0 0 0 0 0

-5.6417 2.5462 -2.5154 N 0 0 0 0 0 0 0 0 0 0 0 0

1.1636 -1.5444 0.1849 C 0 0 0 0 0 0 0 0 0 0 0 0

1.5375 -0.2945 1.4348 S 0 0 0 0 0 0 0 0 0 0 0 0

3.1145 0.3672 0.8591 C 0 0 0 0 0 0 0 0 0 0 0 0

3.5691 1.4624 1.8524 C 0 0 0 0 0 0 0 0 0 0 0 0

4.9369 2.1035 1.5036 C 0 0 1 0 0 0 0 0 0 0 0 0

5.4558 4.3035 2.0858 O 0 0 0 0 0 0 0 0 0 0 0 0

5.4788 2.8920 3.6317 O 0 0 0 0 0 0 0 0 0 0 0 0

5.3104 3.1417 2.4458 C 0 0 0 0 0 0 0 0 0 0 0 0

5.9836 1.0716 1.4496 N 0 0 0 0 0 0 0 0 0 0 0 0

0.0538 -3.4352 -1.3036 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.7701 -2.1547 -1.9536 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.8568 -2.3641 0.9116 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1486 -2.6169 1.5294 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4888 -4.3374 -1.9319 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4794 -4.3762 0.8706 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.1083 -1.2652 0.7841 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3842 1.9482 -3.3397 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.4159 2.2792 -2.0633 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.6871 3.2274 -3.1537 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9459 -2.3071 0.1796 H 0 0 0 0 0 0 0 0 0 0 0 0

1.1214 -1.0782 -0.8024 H 0 0 0 0 0 0 0 0 0 0 0 0

3.0048 0.7884 -0.1429 H 0 0 0 0 0 0 0 0 0 0 0 0

3.8443 -0.4444 0.8218 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8069 2.2489 1.8806 H 0 0 0 0 0 0 0 0 0 0 0 0

3.6234 1.0263 2.8558 H 0 0 0 0 0 0 0 0 0 0 0 0

4.8631 2.5253 0.4960 H 0 0 0 0 0 0 0 0 0 0 0 0

5.6704 4.9311 2.6644 H 0 0 0 0 0 0 0 0 0 0 0 0

6.8714 1.5233 1.2249 H 0 0 0 0 0 0 0 0 0 0 0 0

6.0650 0.6664 2.3848 H 0 0 0 0 0 0 0 0 0 0 0 0

1 7 1 0 0 0 0

2 1 1 0 0 0 0

2 6 1 0 0 0 0

3 2 1 0 0 0 0

3 8 1 0 0 0 0

3 4 1 0 0 0 0

4 5 1 0 0 0 0

5 1 1 0 0 0 0

5 18 1 0 0 0 0

8 9 4 0 0 0 0

8 10 4 0 0 0 0

9 11 4 0 0 0 0

9 12 4 0 0 0 0

10 13 4 0 0 0 0

11 14 4 0 0 0 0

11 13 4 0 0 0 0

12 15 4 0 0 0 0

14 16 4 0 0 0 0

14 17 1 0 0 0 0

15 16 4 0 0 0 0

18 19 1 0 0 0 0

20 19 1 0 0 0 0

20 21 1 0 0 0 0

22 21 1 0 0 0 0

22 26 1 0 0 0 0

22 25 1 0 0 0 0

23 25 1 0 0 0 0

25 24 2 0 0 0 0

1 27 1 0 0 0 0

2 28 1 0 0 0 0

3 29 1 0 0 0 0

5 30 1 0 0 0 0

6 31 1 0 0 0 0

7 32 1 0 0 0 0

10 33 1 0 0 0 0

15 34 1 0 0 0 0

17 35 1 0 0 0 0

17 36 1 0 0 0 0

18 37 1 0 0 0 0

18 38 1 0 0 0 0

20 39 1 0 0 0 0

20 40 1 0 0 0 0

21 41 1 0 0 0 0

21 42 1 0 0 0 0

22 43 1 0 0 0 0

23 44 1 0 0 0 0

26 45 1 0 0 0 0

26 46 1 0 0 0 0

M END): 24 ms

reading 46 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

46 atoms created

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

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
S-Adenosyl-L-homocysteine (SAH) is the biosynthetic precursor to homocysteine. SAH is formed by the demethylation of S-adenosyl-L-methionine. Adenosylhomocysteinase converts SAH into homocysteine and adenosine.
Read full article at Wikipedia

Formula

C14H20N6O5S

Net Charge

Average Mass

384.41204

Monoisotopic Mass

384.12159

InChI

InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1

InChIKey

ZJUKTBDSGOFHSH-WFMPWKQPSA-N

SMILES

N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1cnc2c(N)ncnc12)C(O)=O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

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

Biological Role(s):	fundamental metabolite Any metabolite produced by all living cells. cofactor An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group). EC 2.1.1.79 (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor An EC 2.1.1.* (methyltransferases) inhibitor that interferes with the action of cyclopropane fatty acid synthase (EC 2.1.1.79). EC 2.1.1.72 [site-specific DNA-methyltransferase (adenine-specific)] inhibitor An EC 2.1.1.* (methyltransferases) inhibitor that interferes with the action of site-specific DNA-methyltransferase (adenine-specific), EC 2.1.1.72. epitope The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	S-adenosyl-L-homocysteine (CHEBI:16680) has role cofactor (CHEBI:23357) S-adenosyl-L-homocysteine (CHEBI:16680) has role EC 2.1.1.72 [site-specific DNA-methyltransferase (adenine-specific)] inhibitor (CHEBI:65065) S-adenosyl-L-homocysteine (CHEBI:16680) has role EC 2.1.1.79 (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor (CHEBI:65064) S-adenosyl-L-homocysteine (CHEBI:16680) has role epitope (CHEBI:53000) S-adenosyl-L-homocysteine (CHEBI:16680) has role fundamental metabolite (CHEBI:78675) S-adenosyl-L-homocysteine (CHEBI:16680) is a adenosines (CHEBI:22260) S-adenosyl-L-homocysteine (CHEBI:16680) is a homocysteine derivative (CHEBI:136505) S-adenosyl-L-homocysteine (CHEBI:16680) is a homocysteines (CHEBI:24610) S-adenosyl-L-homocysteine (CHEBI:16680) is a organic sulfide (CHEBI:16385) S-adenosyl-L-homocysteine (CHEBI:16680) is conjugate acid of S-adenosyl-L-homocysteinate (CHEBI:67009) S-adenosyl-L-homocysteine (CHEBI:16680) is tautomer of S-adenosyl-L-homocysteine zwitterion (CHEBI:57856)

Incoming	S-adenosyl-L-homocysteinate (CHEBI:67009) is conjugate base of S-adenosyl-L-homocysteine (CHEBI:16680) S-adenosyl-L-homocysteine zwitterion (CHEBI:57856) is tautomer of S-adenosyl-L-homocysteine (CHEBI:16680)

IUPAC Name

S-(5'-deoxyadenosin-5'-yl)-L-homocysteine

Synonyms	Sources
(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoic acid	PDBeChem
2-S-adenosyl-L-homocysteine	HMDB
Adenosyl-L-homocysteine	HMDB
adenosylhomocysteine	MetaCyc
AdoHcy	ChEBI
S-(5'-adenosyl)-L-homocysteine	HMDB
S-(5'-adenosyl)-L-homocysteine	ChEBI
S-[1-(adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl]-L-homocysteine	IUPAC
S-Adenosyl-L-homocysteine	KEGG COMPOUND
S-ADENOSYL-L-HOMOCYSTEINE	PDBeChem
S-Adenosylhomocysteine	KEGG COMPOUND
SAH	MetaCyc

Manual Xrefs	Databases
ADENOSYL-HOMO-CYS	MetaCyc
C00007230	KNApSAcK
C00021	KEGG COMPOUND
DB01752	DrugBank
HMDB0000939	HMDB
S-Adenosyl-L-homocysteine	Wikipedia
SAH	PDBeChem
View more database links

Registry Numbers	Types	Sources
692100	Gmelin Registry Number	Gmelin
979-92-0	CAS Registry Number	KEGG COMPOUND
979-92-0	CAS Registry Number	ChemIDplus
99188	Reaxys Registry Number	Reaxys

Citations

Last Modified

08 March 2017

CHEBI:16680 - S-adenosyl-L-homocysteine

ChEBI is part of the ELIXIR infrastructure