metformin (CHEBI:6801)

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CHEBI:6801 - metformin

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ChEBI Name	metformin

ChEBI ID	CHEBI:6801

Definition	A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB9454820, eMolecules:530768, Selleckchem:pmsf-phenylmethylsulfonyl-fluoride, ZINC000008220691

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

MF8 - Ideal conformer

Mrv1927 06102113323D

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Time for openFile(MF8 - Ideal conformer

Mrv1927 06102113323D

20 19 0 0 0 0 999 V2000

-2.8810 -1.0200 0.0970 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.8880 -0.1850 -0.0180 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.5890 -0.6460 0.0420 N 0 0 0 0 0 0 0 0 0 0 0 0

-2.1340 1.1550 -0.2010 N 0 0 0 0 0 0 0 0 0 0 0 0

2.0200 -1.6460 -0.1020 C 0 0 0 0 0 0 0 0 0 0 0 0

1.7550 -0.2080 -0.0090 N 0 0 0 0 0 0 0 0 0 0 0 0

0.2250 1.5270 0.1440 N 0 0 0 0 0 0 0 0 0 0 0 0

0.4610 0.2490 0.0600 C 0 0 0 0 0 0 0 0 0 0 0 0

2.8700 0.7430 0.0100 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.7070 -1.9680 0.2040 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9000 1.5700 0.2250 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5410 1.6860 -0.7550 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4130 -1.6000 0.0720 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9630 2.1570 0.1560 H 0 0 0 0 0 0 0 0 0 0 0 0

3.1120 1.0390 -1.0100 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5860 1.6230 0.5870 H 0 0 0 0 0 0 0 0 0 0 0 0

3.7400 0.2730 0.4690 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1200 -2.0630 0.9000 H 0 0 0 0 0 0 0 0 0 0 0 0

1.1940 -2.1350 -0.6190 H 0 0 0 0 0 0 0 0 0 0 0 0

2.9440 -1.8100 -0.6570 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 2 0 0 0 0

2 4 1 0 0 0 0

2 3 1 0 0 0 0

3 8 1 0 0 0 0

8 7 2 0 0 0 0

8 6 1 0 0 0 0

6 9 1 0 0 0 0

6 5 1 0 0 0 0

1 10 1 0 0 0 0

4 11 1 0 0 0 0

4 12 1 0 0 0 0

3 13 1 0 0 0 0

7 14 1 0 0 0 0

9 15 1 0 0 0 0

9 16 1 0 0 0 0

9 17 1 0 0 0 0

5 18 1 0 0 0 0

5 19 1 0 0 0 0

5 20 1 0 0 0 0

M END): 21 ms

reading 20 atoms

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1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

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Molfile expand

Wikipedia	License
In biochemistry, phenylmethylsulfonyl fluoride (PMSF) is a serine protease inhibitor (serine hydrolase inactivator) commonly used in the preparation of cell lysates. PMSF does not inactivate all serine proteases. The effective concentration of PMSF is between 0.1 - 1 mM. The half-life is short in aqueous solutions (110 min at pH 7, 55 min at pH 7.5, and 35 min at pH 8, all at 25 °C). At 4˚C, pH 8, PMSF is almost completely degraded after 1 day. Stock solutions are usually made up in anhydrous ethanol, isopropanol, or corn oil and diluted immediately before use. PMSF reacts specifically with the active site serine residue in serine hydrolases. It does not bind to any other serine residues in the protein. This is a result of the hyperactivity of that serine residue caused by the specific environmental conditions in the enzyme's active site (catalytic triad). Because PMSF bonds covalently to the enzyme, the complex can be viewed by X-ray crystallography; it can therefore be used as a chemical label to identify an essential active site serine in an enzyme. Enzyme(active)Ser-O-H + F-SO2CH2C6H5 → EnzymeSer-O-SO2CH2C6H5 + HF Serine protease + PMSF → Irreversible enzyme-PMS complex + HF The median lethal dose between 150–215 mg/kg (acetylcholine esterase inactivator). PMSF should be handled only inside a fume hood and while wearing gloves. DMSO is sometimes recommended as solvent for stock solutions, but should not be used as it makes intact skin permeable to PMSF.
Read full article at Wikipedia

Formula

C4H11N5

Net Charge

Average Mass

129.167

Monoisotopic Mass

129.10145

InChI

InChI=1S/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8)

InChIKey

XZWYZXLIPXDOLR-UHFFFAOYSA-N

SMILES

CN(C)C(=N)NC(N)=N

Roles Classification
Chemical Role(s):	environmental contaminant Any minor or unwanted substance introduced into the environment that can have undesired effects.

Biological Role(s):	xenobiotic A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.

Application(s):	hypoglycemic agent A drug which lowers the blood glucose level. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	metformin (CHEBI:6801) has functional parent biguanide (CHEBI:3095) metformin (CHEBI:6801) has role environmental contaminant (CHEBI:78298) metformin (CHEBI:6801) has role geroprotector (CHEBI:176497) metformin (CHEBI:6801) has role hypoglycemic agent (CHEBI:35526) metformin (CHEBI:6801) has role xenobiotic (CHEBI:35703) metformin (CHEBI:6801) is a guanidines (CHEBI:24436) metformin (CHEBI:6801) is conjugate base of metformin(1+) (CHEBI:90688)

Incoming	metformin(1+) (CHEBI:90688) is conjugate acid of metformin (CHEBI:6801)

IUPAC Name

N,N-dimethyltriimidodicarbonic diamide

INNs	Sources
metformin	WHO MedNet
metformina	WHO MedNet
metformine	WHO MedNet
metforminum	WHO MedNet

Synonyms	Sources
1,1-dimethylbiguanide	ChemIDplus
dimethylbiguanide	ChemIDplus
dimethyldiguanide	ChemIDplus
LA 6023	DrugBank
LA-6023	ChemIDplus
N,N-dimethylbiguanide	ChemIDplus
N,N-dimethyldiguanide	ChemIDplus
N,N-dimethylguanylguanidine	DrugCentral
N,N-dimethylimidodicarbonimidic diamide	IUPAC
N¹,N¹-dimethylbiguanide	ChemIDplus

Manual Xrefs	Databases
1725	DrugCentral
C07151	KEGG COMPOUND
D04966	KEGG DRUG
DB00331	DrugBank
FDB022739	FooDB
HMDB0001921	HMDB
LSM-4730	LINCS
Metformin	Wikipedia
MF8	PDBeChem
View more database links

Registry Numbers	Types	Sources
606492	Reaxys Registry Number	Reaxys
657-24-9	CAS Registry Number	ChemIDplus

Citations	Types	Sources
10900588	PubMed citation	Europe PMC
10983737	PubMed citation	Europe PMC
10999803	PubMed citation	Europe PMC
11012555	PubMed citation	Europe PMC
11126815	PubMed citation	Europe PMC
11192132	PubMed citation	Europe PMC
11257323	PubMed citation	Europe PMC
11544610	PubMed citation	Europe PMC
11772907	PubMed citation	Europe PMC
12086935	PubMed citation	Europe PMC
12406042	PubMed citation	Europe PMC
12436333	PubMed citation	Europe PMC
12630933	PubMed citation	Europe PMC
12909816	PubMed citation	Europe PMC
15261814	PubMed citation	Europe PMC
15606381	PubMed citation	Europe PMC
15650645	PubMed citation	Europe PMC
15717887	PubMed citation	Europe PMC
15932841	PubMed citation	Europe PMC
16294070	PubMed citation	Europe PMC
16520442	PubMed citation	Europe PMC
16941277	PubMed citation	Europe PMC
17062558	PubMed citation	Europe PMC
18212742	PubMed citation	Europe PMC
18608522	PubMed citation	Europe PMC
23077661	PubMed citation	Europe PMC
23540700	PubMed citation	Europe PMC
24428821	PubMed citation	Europe PMC
28919040	PubMed citation	Europe PMC
31208831	PubMed citation	Europe PMC
33191721	PubMed citation	Europe PMC

Last Modified

26 October 2021

General Comment
2014-10-29	Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag

CHEBI:6801 - metformin

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