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Identification
NameS-Adenosyl-L-Homocysteine
Accession NumberDB01752  (EXPT02842)
Typesmall molecule
Groupsexperimental
Description

5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosine. Formed from S-adenosylmethionine after transmethylation reactions. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number979-92-0
WeightAverage: 384.411
Monoisotopic: 384.12158847
Chemical FormulaC14H20N6O5S
InChI KeyZJUKTBDSGOFHSH-SRMDEQNCSA-N
InChI
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
IUPAC Name
(2S)-2-amino-4-({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid
SMILES
N[C@@H](CCSC[C@@H]1O[C@H]([C@H](O)[C@H]1O)N1C=NC2=C1N=CN=C2N)C(O)=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassGlycosyl Compounds
Direct parentPurine Nucleosides and Analogues
Alternative parentsGlycoamino Acids and Derivatives; Alpha Amino Acids and Derivatives; Pentoses; Purines and Purine Derivatives; Aminopyrimidines and Derivatives; Amino Fatty Acids; Primary Aromatic Amines; N-substituted Imidazoles; Tetrahydrofurans; Oxolanes; 1,2-Diols; Secondary Alcohols; Carboxylic Acids; Enolates; Ethers; Polyamines; Thioethers; Monoalkylamines
Substituentsalpha-amino acid or derivative; pentose monosaccharide; purine; imidazopyrimidine; aminopyrimidine; pyrimidine; primary aromatic amine; monosaccharide; n-substituted imidazole; tetrahydrofuran; imidazole; oxolane; azole; 1,2-diol; secondary alcohol; enolate; polyamine; ether; carboxylic acid; carboxylic acid derivative; thioether; alcohol; primary aliphatic amine; primary amine; organonitrogen compound; amine
Classification descriptionThis compound belongs to the purine nucleosides and analogues. These are compounds comprising a purine base attached to a sugar.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9626
Blood Brain Barrier - 0.6261
Caco-2 permeable - 0.8056
P-glycoprotein substrate Substrate 0.6112
P-glycoprotein inhibitor I Non-inhibitor 0.9437
P-glycoprotein inhibitor II Non-inhibitor 0.9883
Renal organic cation transporter Non-inhibitor 0.9179
CYP450 2C9 substrate Non-substrate 0.8742
CYP450 2D6 substrate Non-substrate 0.8034
CYP450 3A4 substrate Non-substrate 0.5
CYP450 1A2 substrate Non-inhibitor 0.9028
CYP450 2C9 substrate Non-inhibitor 0.9086
CYP450 2D6 substrate Non-inhibitor 0.9295
CYP450 2C19 substrate Non-inhibitor 0.8862
CYP450 3A4 substrate Non-inhibitor 0.9017
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9323
Ames test Non AMES toxic 0.6549
Carcinogenicity Non-carcinogens 0.9345
Biodegradation Not ready biodegradable 0.9885
Rat acute toxicity 2.3223 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9744
hERG inhibition (predictor II) Non-inhibitor 0.7908
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility4.08e+00 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 area182.63ChemAxon
rotatable bond count7ChemAxon
refractivity92.72ChemAxon
polarizability38.21ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Hideaki Yamada, Sakayu Shimizu, Shozo Shiozaki, “Process for producing S-adenosyl-L-homocysteine.” U.S. Patent US4605625, issued March, 1978.

US4605625
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC00021
PubChem Compound46936206
PubChem Substance46508993
ChemSpider188
ChEBI16680
ChEMBL
HETSAH
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Release factor glutamine methyltransferase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Release factor glutamine methyltransferase P0ACC1 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

2. Cap-specific mRNA (nucleoside-2'-O-)-methyltransferase

Kind: protein

Organism: VACV

Pharmacological action: unknown

Components

Name UniProt ID Details
Cap-specific mRNA (nucleoside-2'-O-)-methyltransferase P07617 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

3. Cobalt-precorrin-4 C(11)-methyltransferase

Kind: protein

Organism: Bacillus megaterium

Pharmacological action: unknown

Components

Name UniProt ID Details
Cobalt-precorrin-4 C(11)-methyltransferase O87696 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

4. Protein-L-isoaspartate(D-aspartate) O-methyltransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Protein-L-isoaspartate(D-aspartate) O-methyltransferase P22061 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

5. Genome polyprotein

Kind: protein

Organism: DENV-2

Pharmacological action: unknown

Components

Name UniProt ID Details
Genome polyprotein P12823 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

6. Phenylethanolamine N-methyltransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Phenylethanolamine N-methyltransferase P11086 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

7. Cyclopropane mycolic acid synthase 2

Kind: protein

Organism: Mycobacterium tuberculosis

Pharmacological action: unknown

Components

Name UniProt ID Details
Cyclopropane mycolic acid synthase 2 P0A5P0 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

8. Modification methylase RsrI

Kind: protein

Organism: Rhodobacter sphaeroides

Pharmacological action: unknown

Components

Name UniProt ID Details
Modification methylase RsrI P14751 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

9. Release factor glutamine methyltransferase

Kind: protein

Organism: Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)

Pharmacological action: unknown

Components

Name UniProt ID Details
Release factor glutamine methyltransferase Q9WYV8 Details

10. Protein arginine N-methyltransferase 3

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Protein arginine N-methyltransferase 3 O60678 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

11. Histamine N-methyltransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Histamine N-methyltransferase P50135 Details

12. Ribosomal RNA small subunit methyltransferase H

Kind: protein

Organism: Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)

Pharmacological action: unknown

Components

Name UniProt ID Details
Ribosomal RNA small subunit methyltransferase H Q9WZX6 Details

13. rRNA adenine N-6-methyltransferase

Kind: protein

Organism: Bacillus subtilis

Pharmacological action: unknown

Components

Name UniProt ID Details
rRNA adenine N-6-methyltransferase P13956 Details

14. tRNA (cytosine(38)-C(5))-methyltransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
tRNA (cytosine(38)-C(5))-methyltransferase O14717 Details

15. Glycine N-methyltransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Glycine N-methyltransferase Q14749 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

16. tRNA (cytidine(34)-2'-O)-methyltransferase

Kind: protein

Organism: Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)

Pharmacological action: unknown

Components

Name UniProt ID Details
tRNA (cytidine(34)-2'-O)-methyltransferase P44868 Details

17. Modification methylase PvuII

Kind: protein

Organism: Proteus hauseri

Pharmacological action: unknown

Components

Name UniProt ID Details
Modification methylase PvuII P11409 Details

18. DNA adenine methylase

Kind: protein

Organism: Enterobacteria phage T4

Pharmacological action: unknown

Components

Name UniProt ID Details
DNA adenine methylase P04392 Details

19. Cyclopropane mycolic acid synthase 3

Kind: protein

Organism: Mycobacterium tuberculosis

Pharmacological action: unknown

Components

Name UniProt ID Details
Cyclopropane mycolic acid synthase 3 Q7D9R5 Details

20. Protein arginine N-methyltransferase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Protein arginine N-methyltransferase 1 Q99873 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

21. Siroheme synthase

Kind: protein

Organism: Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)

Pharmacological action: unknown

Components

Name UniProt ID Details
Siroheme synthase P25924 Details

22. Modification methylase HhaI

Kind: protein

Organism: Haemophilus parahaemolyticus

Pharmacological action: unknown

Components

Name UniProt ID Details
Modification methylase HhaI P05102 Details

23. Histone-lysine N-methyltransferase SETD7

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Histone-lysine N-methyltransferase SETD7 Q8WTS6 Details

24. tRNA (guanine-N(1)-)-methyltransferase

Kind: protein

Organism: Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)

Pharmacological action: unknown

Components

Name UniProt ID Details
tRNA (guanine-N(1)-)-methyltransferase P43912 Details

25. Cyclopropane mycolic acid synthase MmaA2

Kind: protein

Organism: Mycobacterium tuberculosis

Pharmacological action: unknown

Components

Name UniProt ID Details
Cyclopropane mycolic acid synthase MmaA2 Q79FX6 Details

26. Diphthine synthase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Diphthine synthase Q9H2P9 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

27. RdmB

Kind: protein

Organism: Streptomyces purpurascens

Pharmacological action: unknown

Components

Name UniProt ID Details
RdmB Q54527 Details

28. tRNA (guanine-N(1)-)-methyltransferase

Kind: protein

Organism: Shigella flexneri

Pharmacological action: unknown

Components

Name UniProt ID Details
tRNA (guanine-N(1)-)-methyltransferase P0A876 Details

29. Uroporphyrinogen-III C-methyltransferase

Kind: protein

Organism: Pseudomonas denitrificans

Pharmacological action: unknown

Components

Name UniProt ID Details
Uroporphyrinogen-III C-methyltransferase P21631 Details

30. Uncharacterized protein

Kind: protein

Organism: Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)

Pharmacological action: unknown

Components

Name UniProt ID Details
Uncharacterized protein Q5SKH6 Details

31. Chemotaxis protein methyltransferase

Kind: protein

Organism: Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)

Pharmacological action: unknown

Components

Name UniProt ID Details
Chemotaxis protein methyltransferase P07801 Details

32. Modification methylase TaqI

Kind: protein

Organism: Thermus aquaticus

Pharmacological action: unknown

Components

Name UniProt ID Details
Modification methylase TaqI P14385 Details

33. Protein-L-isoaspartate O-methyltransferase

Kind: protein

Organism: Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)

Pharmacological action: unknown

Components

Name UniProt ID Details
Protein-L-isoaspartate O-methyltransferase Q56308 Details

34. Catechol O-methyltransferase domain-containing protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Catechol O-methyltransferase domain-containing protein 1 Q86VU5 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

35. Carminomycin 4-O-methyltransferase

Kind: protein

Organism: Streptomyces peucetius

Pharmacological action: unknown

Components

Name UniProt ID Details
Carminomycin 4-O-methyltransferase Q06528 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

36. Guanidinoacetate N-methyltransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Guanidinoacetate N-methyltransferase Q14353 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

Enzymes

1. Histamine N-methyltransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Histamine N-methyltransferase P50135 Details
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:15