FComEx: S-(5'-Adenosyl)-L-homocysteine (PC000185)

Record Information

Version

1.0

Creation date

2015-10-09 22:29:07 UTC

Update date

2017-01-19 02:36:15 UTC

FoodComEx ID

PC000185

FoodDB Record

FDB022327

Chemical Information

Name

S-(5'-Adenosyl)-L-homocysteine

Description

S-Adenosylhomocysteine, also known as adenosyl-homo-cys or adohcy, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. An organic sulfide that is the S-adenosyl derivative of L-homocysteine. S-Adenosylhomocysteine is a very strong basic compound (based on its pKa). S-Adenosylhomocysteine exists in all living species, ranging from bacteria to humans. Outside of the human body, S-Adenosylhomocysteine has been detected, but not quantified in, several different foods, such as arrowhead, guava, purslanes, kiwis, and gooseberries. This could make S-adenosylhomocysteine a potential biomarker for the consumption of these foods. S-Adenosylhomocysteine is a potentially toxic compound.

CAS Number

979-92-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoate	Generator
(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoic acid	ChEBI
(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulphanyl)butanoate	Generator
(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulphanyl)butanoic acid	Generator
(S)-5'-(S)-(3-Amino-3-carboxypropyl)-5'-thioadenosine	hmdb
2-S-adenosyl-L-homocysteine	hmdb
5'-Deoxy-S-adenosyl-L-homocysteine	hmdb
5'-S-(3-amino-3-carboxypropyl)-5'-thio-L-Adenosine	hmdb
Adenosyl-homo-CYS	hmdb
Adenosyl-L-homocysteine	hmdb
Adenosylhomo-CYS	hmdb
Adenosylhomocysteine	hmdb
AdoHcy	ChEBI
Formycinylhomocysteine	hmdb
L-5'-S-(3-amino-3-carboxypropyl)-5'-thior-Adenosine	hmdb
L-S-adenosyl-Homocysteine	hmdb
L-S-Adenosylhomocysteine	hmdb
S-(5'-Adenosyl)-L-homocysteine	hmdb
S-(5'-Deoxyadenosin-5'-yl)-L-homocysteine	hmdb
S-(5'-Deoxyadenosine-5')-L-homocysteine	HMDB
S-[1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl]-L-homocysteine	Generator
S-[1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl]-L-homocysteine	ChEBI
S-[1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl]-L-homocysteine	Generator
S-Adenosyl-homocysteine	hmdb
S-Adenosyl-L-homocysteine	hmdb
S-Adenosylhomocysteine	ChEBI
SAH	ChEBI

Chemical Formula

C14H20N6O5S

IUPAC name

(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid

InChI Identifier

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

InChI Key

ZJUKTBDSGOFHSH-WFMPWKQPSA-N

Isomeric SMILES

N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)=O

Average Molecular Weight

384.411

Monoisotopic Molecular Weight

384.12158847

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents