Record Information
Version1.0
Creation date2015-05-07 21:09:49 UTC
Update date2019-11-26 03:22:10 UTC
Primary IDFDB031150
Secondary Accession Numbers
  • FDB022327
Chemical Information
FooDB NameS-adenosyl-L-homocysteine
DescriptionS-adenosylhomocysteine, also known as adohcy or sah, is a member of the class of compounds known as 5'-deoxy-5'-thionucleosides. 5'-deoxy-5'-thionucleosides are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group. S-adenosylhomocysteine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). S-adenosylhomocysteine can be found in a number of food items such as rapini, european plum, rambutan, and pepper (c. pubescens), which makes S-adenosylhomocysteine a potential biomarker for the consumption of these food products. S-adenosylhomocysteine can be found primarily in blood, cerebrospinal fluid (CSF), feces, and urine, as well as throughout most human tissues. S-adenosylhomocysteine exists in all living species, ranging from bacteria to humans. In humans, S-adenosylhomocysteine is involved in several metabolic pathways, some of which include phosphatidylcholine biosynthesis PC(14:0/18:3(9Z,12Z,15Z)), phosphatidylcholine biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:0), phosphatidylcholine biosynthesis PC(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)), and phosphatidylcholine biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)). S-adenosylhomocysteine is also involved in several metabolic disorders, some of which include 3-phosphoglycerate dehydrogenase deficiency, hawkinsinuria, non ketotic hyperglycinemia, and tyrosine hydroxylase deficiency. Moreover, S-adenosylhomocysteine is found to be associated with neurodegenerative disease and parkinson's disease. S-adenosylhomocysteine is a non-carcinogenic (not listed by IARC) potentially toxic compound. S-Adenosyl-L-homocysteine (SAH) is an amino acid derivative used in several metabolic pathways in most organisms. It is an intermediate in the synthesis of cysteine and adenosine .
CAS Number979-92-0
Structure
Thumb
Synonyms
SynonymSource
(2S)-2-Amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoic acidChEBI
2-S-Adenosyl-L-homocysteineChEBI
Adenosyl-L-homocysteineChEBI
AdenosylhomocysteineChEBI
AdoHcyChEBI
S-(5'-Adenosyl)-L-homocysteineChEBI
S-[1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl]-L-homocysteineChEBI
SAHChEBI
(2S)-2-Amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoateGenerator
(2S)-2-Amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulphanyl)butanoateGenerator
(2S)-2-Amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulphanyl)butanoic acidGenerator
S-[1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl]-L-homocysteineGenerator
S-[1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl]-L-homocysteineGenerator
(S)-5'-(S)-(3-Amino-3-carboxypropyl)-5'-thioadenosineHMDB
5'-Deoxy-S-adenosyl-L-homocysteineHMDB
5'-S-(3-Amino-3-carboxypropyl)-5'-thio-L-adenosineHMDB
Adenosyl-homo-cysHMDB
Adenosylhomo-cysHMDB
FormycinylhomocysteineHMDB
L-5'-S-(3-Amino-3-carboxypropyl)-5'-thior-adenosineHMDB
L-S-Adenosyl-homocysteineHMDB
L-S-AdenosylhomocysteineHMDB
S-(5'-Deoxyadenosin-5'-yl)-L-homocysteineHMDB
S-(5'-Deoxyadenosine-5')-L-homocysteineHMDB
S-Adenosyl-homocysteineHMDB
S-Adenosyl-L-homocysteineHMDB
Adenosylhomocysteine, SHMDB
S AdenosylhomocysteineHMDB
Predicted Properties
PropertyValueSource
Water Solubility4.08 g/LALOGPS
logP-2.4ALOGPS
logP-4ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.81ChemAxon
pKa (Strongest Basic)9.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area182.63 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity92.72 m³·mol⁻¹ChemAxon
Polarizability38.41 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC14H20N6O5S
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 IdentifierInChI=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
Isomeric SMILESN[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)=O
Average Molecular Weight384.411
Monoisotopic Molecular Weight384.12158847
Classification
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a6u-9853000000-441f171739659ea2b5f6Spectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004r-7096060000-d32383fe3b85ef1b9032Spectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(5'-Adenosyl)-L-homocysteine, TMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-0943000000-80fa5c7d919e1085bc5dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-3f143852503952daa0a8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0900000000-23694a4b657a3478ad91Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udr-0980000000-a8f61dcdc8693e2725f5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00kf-0974000000-b3f3632635b2847bf4d2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-188a77c79aaefae8a184Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-b848c20d743785117445Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udr-0980000000-64b7b303fc07300e0782Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0319020200-859d659a39a790a582f1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-53acf4e10681047da062Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0910000000-5896502e31d66786e12aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0009000000-01ea51599f8d30dec7feSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0409000100-2de58945ab0dfa81f099Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-1900000000-a640f1a0bafd33afdd2dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0910000000-5f685035af9b243ccff2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0009000000-8d01fd0969e47d3bcc5cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-2901000000-6c40a4a43a8c3e142eceSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0902000000-c6c0d5529cf011d89f7bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-53acf4e10681047da062Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1905000000-71a19cb77ac6797e6d81Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-11e0ecd68eec9b6ef4f5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-5900000000-c10849015d4b1c3ef749Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0925000000-384762ca7868d8aa06ddSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-2fb047bdcd6fb31842eaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-2900000000-a6bc4489e6fe48ead399Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference