Showing Compound Card for S-Adenosylmethionine (CDB004888)

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Record Information
Version1.0
Created at2020-04-17 18:47:12 UTC
Updated at2020-12-07 19:11:12 UTC
CannabisDB IDCDB004888
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameS-Adenosylmethionine
DescriptionS-Adenosylmethionine, also known as SAM or adomet, belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group. S-Adenosylmethionine is a very strong basic compound (based on its pKa). S-Adenosylmethionine exists in all living species, ranging from bacteria to humans. Within humans, S-adenosylmethionine participates in a number of enzymatic reactions. In particular, S-adenosylmethionine and glycine can be converted into S-adenosylhomocysteine and sarcosine; which is catalyzed by the enzyme dna (cytosine-5)-methyltransferase 1. In addition, S-adenosylmethionine can be converted into S-adenosylmethioninamine; which is catalyzed by the enzyme S-adenosylmethionine decarboxylase proenzyme. In humans, S-adenosylmethionine is involved in the metabolic disorder called the glycine n-methyltransferase deficiency pathway. Outside of the human body, S-Adenosylmethionine has been detected, but not quantified in, several different foods, such as malabar plums, sunflowers, purple mangosteens, cherry tomato, and pigeon pea. This could make S-adenosylmethionine a potential biomarker for the consumption of these foods. S-Adenosylmethionine is a potentially toxic compound. A sulfonium compound that is the S-adenosyl derivative of L-methionine. S-Adenosylmethionine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Chemical FormulaC15H23N6O5S
Average Molecular Weight399.45
Monoisotopic Molecular Weight399.1451
IUPAC Name[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium
Traditional NameSAMe
CAS Registry Number485-80-3
SMILES
C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1
InChI KeyMEFKEPWMEQBLKI-AIRLBKTGSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
Class5'-deoxyribonucleosides
Sub Class5'-deoxy-5'-thionucleosides
Direct Parent5'-deoxy-5'-thionucleosides
Alternative Parents
Substituents
  • 5'-deoxy-5'-thionucleoside
  • Methionine or derivatives
  • N-glycosyl compound
  • Glycosyl compound
  • Pentose monosaccharide
  • 6-aminopurine
  • Alpha-amino acid
  • L-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Hydroxy fatty acid
  • Thia fatty acid
  • N-substituted imidazole
  • Fatty acyl
  • Monosaccharide
  • Imidolactam
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Amino acid or derivatives
  • 1,2-diol
  • Amino acid
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Primary aliphatic amine
  • Amine
  • Organonitrogen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point78 °CNot Available
Water Solubility1.19 g/lALOGPS
logP-5.3ChemAxon
Predicted Properties
PropertyValueSource
logP-2ALOGPS
logP-5.3ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)1.7ChemAxon
pKa (Strongest Basic)9.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area182.63 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity96.23 m³·mol⁻¹ChemAxon
Polarizability40.37 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSS-Adenosylmethionine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a5c-5965000000-324e4a3cbf936132bcf1Spectrum
Predicted GC-MSS-Adenosylmethionine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ea-7958582000-3dd40cf273f182ee53ddSpectrum
Predicted GC-MSS-Adenosylmethionine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Transporters
Protein NameGene NameLocusUniprot IDDetails
Putative adenosylhomocysteinase 2AHCYL11p13.2O43865 details
Histone-lysine N-methyltransferase MLLMLL11q23Q03164 details
S-adenosylmethionine mitochondrial carrier proteinSLC25A263p14.1Q70HW3 details
Metal Bindings
Receptors
Protein NameGene NameLocusUniprot IDDetails
Histone-lysine N-methyltransferase, H3 lysine-36 and H4 lysine-20 specificNSD15q35Q96L73 details
Histone-arginine methyltransferase CARM1CARM119p13.2Q86X55 details
Histone-lysine N-methyltransferase EZH2EZH27q35-q36Q15910 details
Histone-lysine N-methyltransferase MLL2MLL212q13.12O14686 details
Histone-lysine N-methyltransferase MLL5MLL57q22.1Q8IZD2 details
Transmembrane O-methyltransferaseLRTOMT11q13.4Q8WZ04 details
Protein arginine N-methyltransferase 1PRMT119q13.3Q99873 details
Protein arginine N-methyltransferase 2PRMT221q22.3P55345 details
Transcriptional Factors
Concentrations Data
Not Available
HMDB IDHMDB0001185
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031152
KNApSAcK IDC00007347
Chemspider ID21169292
KEGG Compound IDC00019
BioCyc IDS-ADENOSYLMETHIONINE
BiGG ID33530
Wikipedia LinkS-Adenosyl_methionine
METLIN ID6064
PubChem Compound34756
PDB IDNot Available
ChEBI ID15414
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 211 proteins in total.

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Enzymes

Enzyme Details
1. Phosphatidylethanolamine N-methyltransferase
General function:
Involved in N-methyltransferase activity
Specific function:
Catalyzes three sequential methylation reactions of phosphatidylethanolamine (PE) by AdoMet, thereby producing phosphatidylcholine (PC).
Gene Name:
PEMT
Uniprot ID:
Q9UBM1
Molecular weight:
23697.395
Enzyme Details
2. Acetylserotonin O-methyltransferase
General function:
Involved in O-methyltransferase activity
Specific function:
Isoform 1 catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine). Isoform 2 and isoform 3 lack enzyme activity.
Gene Name:
ASMT
Uniprot ID:
P46597
Molecular weight:
41660.34
Enzyme Details
3. Methionine synthase
General function:
Involved in cobalamin binding
Specific function:
Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate (By similarity).
Gene Name:
MTR
Uniprot ID:
Q99707
Molecular weight:
140525.91
Enzyme Details
4. Catechol O-methyltransferase
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Enzyme Details
5. Histone-lysine N-methyltransferase, H3 lysine-79 specific
General function:
Involved in DNA binding
Specific function:
Histone methyltransferase. Methylates 'Lys-79' of histone H3. Nucleosomes are preferred as substrate compared to free histones. Binds to DNA.
Gene Name:
DOT1L
Uniprot ID:
Q8TEK3
Molecular weight:
164854.41
Enzyme Details
6. Glycine N-methyltransferase
General function:
Involved in folic acid binding
Specific function:
Catalyzes the methylation of glycine by using S-adenosylmethionine (AdoMet) to form N-methylglycine (sarcosine) with the concomitant production of S-adenosylhomocysteine (AdoHcy). Possible crucial role in the regulation of tissue concentration of AdoMet and of metabolism of methionine.
Gene Name:
GNMT
Uniprot ID:
Q14749
Molecular weight:
32742.0
Enzyme Details
7. Histone-lysine N-methyltransferase SETD7
General function:
Involved in histone-lysine N-methyltransferase activity
Specific function:
Histone methyltransferase that specifically monomethylates 'Lys-4' of histone H3. H3 'Lys-4' methylation represents a specific tag for epigenetic transcriptional activation. Plays a central role in the transcriptional activation of genes such as collagenase or insulin. Recruited by IPF1/PDX-1 to the insulin promoter, leading to activate transcription. Has also methyltransferase activity toward non-histone proteins such as p53/TP53, TAF10, and possibly TAF7 by recognizing and binding the [KR]-[STA]-K in substrate proteins. Monomethylates 'Lys-189' of TAF10, leading to increase the affinity of TAF10 for RNA polymerase II. Monomethylates 'Lys-372' of p53/TP53, stabilizing p53/TP53 and increasing p53/TP53-mediated transcriptional activation.
Gene Name:
SETD7
Uniprot ID:
Q8WTS6
Molecular weight:
40720.595
Enzyme Details
8. S-adenosylmethionine synthase isoform type-2
General function:
Involved in methionine adenosyltransferase activity
Specific function:
Catalyzes the formation of S-adenosylmethionine from methionine and ATP.
Gene Name:
MAT2A
Uniprot ID:
P31153
Molecular weight:
43660.37
Enzyme Details
9. Phenylethanolamine N-methyltransferase
General function:
Involved in methyltransferase activity
Specific function:
Converts noradrenaline to adrenaline.
Gene Name:
PNMT
Uniprot ID:
P11086
Molecular weight:
30854.745
Enzyme Details
10. Diphthine synthase
General function:
Involved in methyltransferase activity
Specific function:
S-adenosyl-L-methionine-dependent methyltransferase that catalyzes the trimethylation of the amino group of the modified target histidine residue in translation elongation factor 2 (EF-2), to form an intermediate called diphthine. The three successive methylation reactions represent the second step of diphthamide biosynthesis (By similarity).
Gene Name:
DPH5
Uniprot ID:
Q9H2P9
Molecular weight:
31651.17

Transporters

Enzyme Details
1. Putative adenosylhomocysteinase 2
General function:
Involved in adenosylhomocysteinase activity
Specific function:
Not Available
Gene Name:
AHCYL1
Uniprot ID:
O43865
Molecular weight:
53753.0
Enzyme Details
2. Histone-lysine N-methyltransferase MLL
General function:
Involved in DNA binding
Specific function:
Histone methyltransferase that plays an essential role in early development and hematopoiesis. Catalytic subunit of the MLL1/MLL complex, a multiprotein complex that mediates both methylation of 'Lys-4' of histone H3 (H3K4me) complex and acetylation of 'Lys-16' of histone H4 (H4K16ac). In the MLL1/MLL complex, it specifically mediates H3K4me, a specific tag for epigenetic transcriptional activation. Has weak methyltransferase activity by itself, and requires other component of the MLL1/MLL complex to obtain full methyltransferase activity. Has no activity toward histone H3 phosphorylated on 'Thr-3', less activity toward H3 dimethylated on 'Arg-8' or 'Lys-9', while it has higher activity toward H3 acetylated on 'Lys-9'. Required for transcriptional activation of HOXA9. Promotes PPP1R15A-induced apoptosis.
Gene Name:
MLL
Uniprot ID:
Q03164
Molecular weight:
432047.735
Enzyme Details
3. S-adenosylmethionine mitochondrial carrier protein
General function:
Involved in binding
Specific function:
Mitochondrial solute carriers shuttle metabolites, nucleotides, and cofactors through the mitochondrial inner membrane. Specifically mediates the transport of S-adenosylmethionine (SAM) into the mitochondria.
Gene Name:
SLC25A26
Uniprot ID:
Q70HW3
Molecular weight:
20116.095

Only showing the first 10 proteins. There are 211 proteins in total.

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