MNNG – N-methyl-N'-nitro-N-nitrosoguanidine

Name
WID	MNNG
Name	N-methyl-N'-nitro-N-nitrosoguanidine
Traditional name	1-methyl-2-nitro-1-nitrosoguanidine
IUPAC name	1-methyl-2-nitro-1-nitrosoguanidine
Cross references	ChEBI: 21759, PubChem: 85240171, KEGG: C14592

Classification
Type	alkylating_agent_methylation

Structure
Empirical formula (pH 7.5)	H₅C₂N₅O₃
SMILES (pH 7.5)	CN(C(=N[N+](=O)[O-])N)N=O
Charge (pH 7.5)	0
Is hydrophobic	False
Molecular weight (Da)	147.09
van der Waals volume (pH 7.5; Å³ molecule^‑1)	109.94
Δ_fG^'o (pH 7.5, 25C, I = 0; kJ mol^‑1)	0.0
logP	-0.440
logD (pH 7.5)	-0.440

Function
Reaction participant	DNA base methylation (thymine ==> 2'-O-methylthymine; N-methyl-N'-nitro-N-nitrosoguanidine) [c]: MNNG + THY ⇒ NNG + O2mTHY DNA base methylation (adenine ==> 7-methyladenine; N-methyl-N'-nitro-N-nitrosoguanidine) [c]: AD + MNNG ⇒ m7AD + NNG DNA base methylation (guanine ==> 7-methylguanine; N-methyl-N'-nitro-N-nitrosoguanidine) [c]: GN + H + MNNG ⇒ m7GN + NNG DNA base methylation (thymine ==> 4'-O-methylthymine; N-methyl-N'-nitro-N-nitrosoguanidine) [c]: MNNG + THY ⇒ NNG + O4mTHY DNA base methylation (cytosine ==> 3-methylcytosine; N-methyl-N'-nitro-N-nitrosoguanidine) [c]: CSN + MNNG ⇒ m3CSN + NNG ... 5 more DNA base methylation (cytosine ==> 2'-O-methylcytosine; N-methyl-N'-nitro-N-nitrosoguanidine) [c]: CSN + MNNG ⇒ NNG + O2mCSN DNA base methylation (adenine ==> 3-methyladenine; N-methyl-N'-nitro-N-nitrosoguanidine) [c]: AD + MNNG ⇒ m3AD + NNG DNA base methylation (adenine ==> 1-methyladenine; N-methyl-N'-nitro-N-nitrosoguanidine) [c]: AD + H + MNNG ⇒ m1AD + NNG DNA base methylation (guanine ==> 6'-O-methylguanine; N-methyl-N'-nitro-N-nitrosoguanidine) [c]: GN + MNNG ⇒ NNG + O6mGN DNA base methylation (guanine ==> 3-methylguanine; N-methyl-N'-nitro-N-nitrosoguanidine) [c]: GN + MNNG ⇒ m3GN + NNG

Comments
Comments	SN1 DNA methylating agent [PUB_0465]. Media concentration set to same concentration as Mg2+.
References	Sedgwick B. Repairing DNA-methylation damage. Nat Rev Mol Cell Biol 5, 148-57 (2004). WholeCell: PUB_0465, PubMed: 15040447

Metadata
Created	2012-10-01 15:07:03
Last updated	2012-10-01 15:12:22