Details of the Drug

General Information of Drug (ID: DMDUN83)

Drug Name

(L-)-S-adenosyl-L-homocysteine

Synonyms

S-Adenosyl-L-homocysteine; S-adenosylhomocysteine; S-adenosyl-L-homocysteine; 979-92-0; AdoHcy; S-(5'-adenosyl)-L-homocysteine; adenosylhomocysteine; Formycinylhomocysteine; Adenosyl-L-homocysteine; S-(5'-deoxyadenosin-5'-yl)-L-homocysteine; 2-S-adenosyl-L-homocysteine; 5'-Deoxy-S-adenosyl-L-homocysteine; S-adenosyl-homocysteine; S-Adenosyl Homocysteine; L-S-Adenosylhomocysteine; L-Homocysteine, S-(5'-deoxyadenosin-5'-yl)-; adenosylhomo-cys; adenosyl-homo-cys; UNII-8K31Q2S66S; (S)-5'-(S)-(3-Amino-3-carboxypropyl)-5'-thioadenosine; BRN 5166233; SAH; S-Adenosylhomocysteine; S-Adenosyl-L-Homocysteine

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

384.41

Logarithm of the Partition Coefficient (xlogp)

-3.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C14H20N6O5S
IUPAC Name: (2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfanyl]butanoic acid
Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CSCC[C@@H](C(=O)O)N)O)O)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
InChIKey: ZJUKTBDSGOFHSH-WFMPWKQPSA-N

Cross-matching ID

PubChem CID: 439155
ChEBI ID: CHEBI:16680
CAS Number: 979-92-0
UNII: 8K31Q2S66S
DrugBank ID: DB01752
TTD ID: D09CLP

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
DNA [cytosine-5]-methyltransferase (DNMT)	TTHVCUP	NOUNIPROTAC	Inhibitor	[2]
DNA [cytosine-5]-methyltransferase 3B (DNMT3B)	TT6VZ78	DNM3B_HUMAN	Inhibitor	[2]
Histamine N-methyltransferase (HNMT)	TT2B6EV	HNMT_HUMAN	Inhibitor	[1]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Adenosylhomocysteinase (AHCY)	OT8UC40I	SAHH_HUMAN	Biotransformations	[3]
Collagen alpha-1(I) chain (COL1A1)	OTI31178	CO1A1_HUMAN	Gene/Protein Processing	[4]
Collagen alpha-2(I) chain (COL1A2)	OTY7G382	CO1A2_HUMAN	Gene/Protein Processing	[4]
DNA cytosine-5)-methyltransferase 1 (DNMT1)	OTM2DGTK	DNMT1_HUMAN	Gene/Protein Processing	[5]
Histone-arginine methyltransferase CARM1 (CARM1)	OT0IPRVR	CARM1_HUMAN	Gene/Protein Processing	[6]
Peroxisome proliferator-activated receptor gamma coactivator 1-alpha (PPARGC1A)	OTHCDQ22	PRGC1_HUMAN	Gene/Protein Processing	[7]
Protein arginine N-methyltransferase 1 (PRMT1)	OTN8GTXW	ANM1_HUMAN	Gene/Protein Processing	[6]
Protein arginine N-methyltransferase 5 (PRMT5)	OTF6IGJS	ANM5_HUMAN	Gene/Protein Processing	[6]
Protein arginine N-methyltransferase 6 (PRMT6)	OT5V3XIN	ANM6_HUMAN	Gene/Protein Processing	[6]
Protein arginine N-methyltransferase 7 (PRMT7)	OTE73PO1	ANM7_HUMAN	Gene/Protein Processing	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
2	Constrained (l-)-S-adenosyl-l-homocysteine (SAH) analogues as DNA methyltransferase inhibitors. Bioorg Med Chem Lett. 2009 May 15;19(10):2742-6.
3	Abnormal Hypermethylation at Imprinting Control Regions in Patients with S-Adenosylhomocysteine Hydrolase (AHCY) Deficiency. PLoS One. 2016 Mar 14;11(3):e0151261. doi: 10.1371/journal.pone.0151261. eCollection 2016.
4	S-adenosylmethionine blocks collagen I production by preventing transforming growth factor-beta induction of the COL1A2 promoter. J Biol Chem. 2005 Sep 2;280(35):30963-74. doi: 10.1074/jbc.M503569200. Epub 2005 Jun 27.
5	Mechanisms for the inhibition of DNA methyltransferases by tea catechins and bioflavonoids. Mol Pharmacol. 2005 Oct;68(4):1018-30. doi: 10.1124/mol.104.008367. Epub 2005 Jul 21.
6	Ribavirin inhibits colorectal cancer growth by downregulating PRMT5 expression and H3R8me2s and H4R3me2s accumulation. Toxicol Appl Pharmacol. 2021 Mar 15;415:115450. doi: 10.1016/j.taap.2021.115450. Epub 2021 Feb 9.
7	A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1 expression and mitochondrial biogenesis. PLoS One. 2012;7(10):e46753. doi: 10.1371/journal.pone.0046753. Epub 2012 Oct 3.