S-adenosyl-L-homocysteine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for S-adenosyl-L-homocysteine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the S-adenosyl-L-homocysteine?

The molecule S-adenosyl-L-homocysteine presents a molecular formula of C14H20N6O5S and its IUPAC name is (2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfanyl]butanoic acid.

S-adenosyl-L-homocysteine (AdoHcy) is a molecule involved in the metabolism of methyl groups. Methyl groups are important for the regulation of many biochemical processes, and AdoHcy is a key intermediate in the methylation cycle..

AdoHcy is formed when S-adenosylmethionine (SAM), the universal methyl donor, donates a methyl group to homocysteine. This reaction is catalyzed by the enzyme methionine adenosyltransferase. AdoHcy can then be recycled back to SAM by the enzyme adenosylhomocysteinase..

AdoHcy is a potent inhibitor of methyltransferases, the enzymes that use SAM to methylate other molecules. This inhibition can lead to the accumulation of AdoHcy and the depletion of SAM, which can disrupt methylation reactions and lead to disease..

AdoHcy has been implicated in a variety of diseases, including cancer, cardiovascular disease, and neurodegenerative disorders. AdoHcy levels are often elevated in patients with these diseases, and AdoHcy has been shown to promote the development of these diseases in animal models..

AdoHcy is a potential therapeutic target for the treatment of these diseases. Inhibitors of AdoHcy hydrolysis are being developed as potential treatments for cancer and cardiovascular disease..

3D structure

Cartesian coordinates

Geometry of S-adenosyl-L-homocysteine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

S-adenosyl-L-homocysteine ZJUKTBDSGOFHSH-WFMPWKQPSA-N chemical compound 2D structure molecule svg
S-adenosyl-L-homocysteine

 

Molecule descriptors

 
IUPAC name(2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfanyl]butanoic acid
InChI codeInChI=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 KeyZJUKTBDSGOFHSH-WFMPWKQPSA-N
SMILESNc1ncnc2c1ncn2[C@@H]1O[C@H](CSCC[C@H](N)C(=O)O)[C@@H](O)[C@H]1O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (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-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoic acid (non-preferred name)
  • (S)-2-Amino-4-((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid
  • (S)-2-amino-4-(((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methylthio)butanoic acid
  • (S)-5'-(S)-(3-Amino-3-carboxypropyl)-5'-thioadenosine
  • 1aqi
  • 1jqd
  • 1nw7
  • 1qan
  • 1s4d
  • 2-S-adenosyl-L-homocysteine
  • 2bqz
  • 2h23
  • 5'-Deoxy-S-adenosyl-L-homocysteine
  • 5'-S-(3-amino-3-carboxypropyl)-5'-thio-L-Adenosine
  • 8K31Q2S66S
  • 979-92-0
  • A858597
  • AS-64957
  • Adenosine, 5'-S-(3-amino-3-carboxypropyl)-5'-thio-, L- (8CI)
  • Adenosyl-L-homocysteine
  • AdoHcy
  • BDBM50009672
  • BRN 5166233
  • C00021
  • CCG-208703
  • CS-0015632
  • 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))-
  • DB01752
  • FT-0771999
  • Formycinylhomocysteine
  • GTPL5265
  • HY-19528
  • Homocysteine, S-adenosyl-, L- (6CI,7CI)
  • L-5'-S-(3-amino-3-carboxypropyl)-5'-thior-Adenosine
  • L-Homocysteine, S-(5'-deoxyadenosin-5'-yl)-
  • L-Homocysteine, S-(5'-deoxyadenosin-5'-yl)- (9CI)
  • L-S-Adenosylhomocysteine
  • L-S-adenosyl-Homocysteine
  • MFCD00037388
  • NCGC00263623-01
  • NCGC00263623-02
  • NCGC00263623-03
  • Q307434
  • S-(5''-adenosyl)-L-homocysteine
  • S-(5''-deoxyadenosin-5''-yl)-L-homocysteine
  • S-(5'-Adenosyl)-L-homocysteine
  • S-(5'-Deoxyadenosine-5')-L-homocysteine
  • S-(5'-adenosyl)-L-homocysteine
  • S-(5'-deoxyadenosin-5'-yl)-L-homocysteine
  • S-Adenosyl Homocysteine
  • S-Adenosyl-L-homocysteine (SAH)
  • S-[1-(adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl]-L-homocysteine
  • S-adenosyl-L-homocysteine
  • S-adenosyl-homocysteine
  • S-adenosylhomocysteine
  • S7868
  • SAH
  • US8895245, S-Adenosyl-L-homocysteine (SAH)
  • adenosine, 5'-S-[(3S)-3-amino-3-carboxypropyl]-5'-thio-
  • adenosyl-homo-cys
  • adenosylhomo-cys
  • adenosylhomocysteine
  • bmse000289

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4228232
  • UNII-8K31Q2S66S
  • AKOS022184395
  • DTXSID30895860
  • CHEMBL418052
  • CHEBI:16680
  • EINECS 213-560-8
  • SCHEMBL8836

Physico-Chemical properties

IUPAC name(2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfanyl]butanoic acid
Molecular formulaC14H20N6O5S
Molecular weight384.411
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity92.81
LogP-0.2
Topological polar surface area207.9

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.