Showing Compound S-adenosyl-L-homocysteine (FDB031150)

Record Information

Version

1.0

Creation date

2015-05-07 21:09:49 UTC

Update date

2025-11-19 03:03:09 UTC

Primary ID

FDB031150

Secondary Accession Numbers

FDB022327

Chemical Information

FooDB Name

S-adenosyl-L-homocysteine

Description

S-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 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)butanoic acid	ChEBI
2-S-Adenosyl-L-homocysteine	ChEBI
Adenosyl-L-homocysteine	ChEBI
Adenosylhomocysteine	ChEBI
AdoHcy	ChEBI
S-(5'-Adenosyl)-L-homocysteine	ChEBI
S-[1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl]-L-homocysteine	ChEBI
SAH	ChEBI
(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}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-[1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl]-L-homocysteine	Generator
S-[1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl]-L-homocysteine	Generator
(S)-5'-(S)-(3-Amino-3-carboxypropyl)-5'-thioadenosine	HMDB
5'-Deoxy-S-adenosyl-L-homocysteine	HMDB
5'-S-(3-Amino-3-carboxypropyl)-5'-thio-L-adenosine	HMDB
Adenosyl-homo-cys	HMDB
Adenosylhomo-cys	HMDB
Formycinylhomocysteine	HMDB
L-5'-S-(3-Amino-3-carboxypropyl)-5'-thior-adenosine	HMDB
L-S-Adenosyl-homocysteine	HMDB
L-S-Adenosylhomocysteine	HMDB
S-(5'-Deoxyadenosin-5'-yl)-L-homocysteine	HMDB
S-(5'-Deoxyadenosine-5')-L-homocysteine	HMDB
S-Adenosyl-homocysteine	HMDB
S-Adenosyl-L-homocysteine	HMDB
Adenosylhomocysteine, S	HMDB
S Adenosylhomocysteine	HMDB

Predicted Properties

Property	Value	Source
Water Solubility	4.08 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-4	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.81	ChemAxon
pKa (Strongest Basic)	9.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	182.63 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	92.72 m³·mol⁻¹	ChemAxon
Polarizability	38.41 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

diol (CHEBI:71176 )
butan-4-olide (CHEBI:71176 )

Ontology

Physiological effect

Health effect:

Health condition:

Neurodegenerative disease

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Role

Indirect biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a6u-9853000000-441f171739659ea2b5f6	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004r-7096060000-d32383fe3b85ef1b9032	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(5'-Adenosyl)-L-homocysteine, TMS_3_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0006-0943000000-80fa5c7d919e1085bc5d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-3f143852503952daa0a8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03di-0900000000-23694a4b657a3478ad91	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udr-0980000000-a8f61dcdc8693e2725f5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00kf-0974000000-b3f3632635b2847bf4d2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-0900000000-188a77c79aaefae8a184	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-b848c20d743785117445	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udr-0980000000-64b7b303fc07300e0782	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0319020200-859d659a39a790a582f1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0900000000-53acf4e10681047da062	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0910000000-5896502e31d66786e12a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0009000000-01ea51599f8d30dec7fe	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0409000100-2de58945ab0dfa81f099	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-1900000000-a640f1a0bafd33afdd2d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0910000000-5f685035af9b243ccff2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0009000000-8d01fd0969e47d3bcc5c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-000i-2901000000-6c40a4a43a8c3e142ece	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0902000000-c6c0d5529cf011d89f7b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0900000000-53acf4e10681047da062	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1905000000-71a19cb77ac6797e6d81	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1900000000-11e0ecd68eec9b6ef4f5	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-5900000000-c10849015d4b1c3ef749	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0925000000-384762ca7868d8aa06dd	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1900000000-2fb047bdcd6fb31842ea	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-2900000000-a6bc4489e6fe48ead399	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Spectrum