Show more...Show more...Show more...Show more...Show more...Show more...Show more...
Record Information
Version1.0
Created at2020-04-17 18:45:30 UTC
Updated at2020-12-07 19:11:09 UTC
CannabisDB IDCDB004872
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameS-Adenosylhomocysteine
DescriptionS-Adenosylhomocysteine, also known as adenosyl-homo-cys or adohcy, 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. An organic sulfide that is the S-adenosyl derivative of L-homocysteine. S-Adenosylhomocysteine is a very strong basic compound (based on its pKa). S-Adenosylhomocysteine exists in all living species, ranging from bacteria to humans. Outside of the human body, S-Adenosylhomocysteine has been detected, but not quantified in, several different foods, such as arrowhead, guava, purslanes, kiwis, and gooseberries. This could make S-adenosylhomocysteine a potential biomarker for the consumption of these foods. S-Adenosylhomocysteine is a potentially toxic compound. S-Adenosylhomocysteine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
Chemical FormulaC14H20N6O5S
Average Molecular Weight384.41
Monoisotopic Molecular Weight384.1216
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
Traditional NameS-adenosyl-L-homocysteine
CAS Registry Number979-92-0
SMILES
N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)=O
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 KeyZJUKTBDSGOFHSH-WFMPWKQPSA-N
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point209 - 211 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
Transporters
Protein NameGene NameLocusUniprot IDDetails
Putative adenosylhomocysteinase 2AHCYL11p13.2O43865 details
Histone-lysine N-methyltransferase MLLMLL11q23Q03164 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 IDHMDB0000939
DrugBank IDDB01752
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031150
KNApSAcK IDC00007230
Chemspider ID388301
KEGG Compound IDC00021
BioCyc IDADENOSYL-HOMO-CYS
BiGG ID33543
Wikipedia LinkS-Adenosyl-L-homocysteine
METLIN ID296
PubChem Compound439155
PDB IDNot Available
ChEBI ID16680
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 175 proteins in total.

Enzymes

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
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
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
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
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
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
General function:
Involved in methyltransferase activity
Specific function:
Converts noradrenaline to adrenaline.
Gene Name:
PNMT
Uniprot ID:
P11086
Molecular weight:
30854.745
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
General function:
Involved in methyltransferase activity
Specific function:
Catalyzes the transfer of a methyl group from AdoMet to trivalent arsenicals producing methylated and dimethylated arsenicals. It methylates arsenite to form methylarsonate, Me-AsO(3)H(2), which is reduced by methylarsonate reductase to methylarsonite, Me-As(OH)2. Methylarsonite is also a substrate and it is converted into the much less toxic compound dimethylarsinate (cacodylate), Me(2)As(O)-OH (By similarity).
Gene Name:
AS3MT
Uniprot ID:
Q9HBK9
Molecular weight:
41747.49
General function:
Involved in transferase activity
Specific function:
Catalyzes the 2-thiolation of uridine at the wobble position (U34) of mitochondrial tRNA(Lys), tRNA(Glu) and tRNA(Gln). Required for the formation of 5-taurinomethyl-2- thiouridine (tm5s2U) of mitochondrial tRNA(Lys), tRNA(Glu), and tRNA(Gln) at the wobble position. ATP is required to activate the C2 atom of the wobble base
Gene Name:
TRMU
Uniprot ID:
O75648
Molecular weight:
47744.3

Transporters

General function:
Involved in adenosylhomocysteinase activity
Specific function:
Not Available
Gene Name:
AHCYL1
Uniprot ID:
O43865
Molecular weight:
53753.0
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

Only showing the first 10 proteins. There are 175 proteins in total.