Adenosylhomocysteine
Basic information
- CAS
75899-14-8- Standard SMILES
Nc1ncnc2c1ncn2[C@@H]1O[C@H](CSCC[C@H](N)C(=O)O)[C@@H](O)[C@H]1O- InChIKey
ZJUKTBDSGOFHSH-WFMPWKQPSA-N- Molecular formula
- C14H20N6O5S
- Average molar mass
- 384.41 g/mol
- Monoisotopic mass
- 384.12158893
Overview
S-adenosyl-L-homocysteine is an organic sulfide that is the S-adenosyl derivative of L-homocysteine. It has a role as a cofactor, an epitope, an EC 2.1.1.79 (cyclopropane-fatty-acyl-phospholipid synthase) inhibitor, an EC 2.1.1.72 [site-specific DNA-methyltransferase (adenine-specific)] inhibitor and a fundamental metabolite. It is a homocysteine derivative, an organic sulfide, a member of adenosines and a member of homocysteines. It is a conjugate acid of a S-adenosyl-L-homocysteinate. It is a tautomer of a S-adenosyl-L-homocysteine zwitterion.
Names & identifiers
- Preferred name
- Adenosylhomocysteine
- IUPAC
- (2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfanyl]butanoic acid
- English name
- D-Ribitol, 5-S-(3-amino-3-carboxypropyl)-1-C-(7-amino-1H-pyrazolo(4,3- d)pyrimidin-3-yl)-1,4-anhydro-5-thio-, (1S,5(S))-
- Molecular formula
- C14H20N6O5S
- Molecular weight
- 384.41
Names & synonyms
S-adenosylhomocysteineS-adenosyl-L-homocysteine979-92-0adenosylhomocysteineS-(5'-adenosyl)-L-homocysteineS-(5'-deoxyadenosin-5'-yl)-L-homocysteineAdenosyl-L-homocysteine2-S-adenosyl-L-homocysteineadenosylhomo-cysL-Homocysteine, S-(5'-deoxyadenosin-5'-yl)-adenosyl-homo-cysCHEBI:16680
Show more names
D-Ribitol, 5-S-(3-amino-3-carboxypropyl)-1-C-(7-amino-1H-pyrazolo(4,3- d)pyrimidin-3-yl)-1,4-anhydro-5-thio-, (1S,5(S))-D-Ribitol, 5-S-[(3S)-3-amino-3-carboxypropyl]-1-C-(7-amino-1H-pyrazolo[4,3-d]pyrimidin-3-yl)-1,4-anhydro-5-thio-, (1S)- (9CI)(S)-2-Amino-4-((((2S,3S,4R,5S)-5-(7-amino-1H-pyrazolo[4,3-d]pyrimidin-3-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid
Adenosylhomocysteine, S8K31Q2S66S(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acidDTXSID30895860(2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfanyl]butanoic acid(2R,3R,4R)-2-adenin-9-yltetrahydrofuran-3,4-diol(2S)-2-amino-4-((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl)methyl)sulfanyl)butanoic acid(2S)-2-amino-4-(((2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl)methylsulfanyl)butanoic acid
Properties
Computed structural properties
- XLogP
- -3.5
- Topological polar surface area
- 208 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 7
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 504
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Melting Point209 - 211 °C
Physical DescriptionSolid
Collision Cross Section
182.7 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
179 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
182.9 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
189.3 Ų [M+Na]+
Physicochemical properties
- Boiling point
- 811.9 · 811.9±65.0 °C(Predicted)
- Density
- 1.656 · 1.656±0.06 g/cm3(Predicted)
- pka
- 2.22 · 2.22±0.10(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Health EffectsChronically high levels of S-adenosylhomocysteine are associated with S-Adenosylhomocysteine (SAH) Hydrolase Deficiency.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemistry & industry
Pharmacology
Tissue LocationsKidney
Cellular LocationsEndoplasmic reticulum
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency
Uses & manufacturing
UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
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Related reactions
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Compound notes
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