1,3-BIS(HYDROXYMETHYL)-5,5-DIMETHYLHYDANTOIN

General Information

Mainterm1,3-BIS(HYDROXYMETHYL)-5,5-DIMETHYLHYDANTOIN
CAS Reg.No.(or other ID)6440-58-0
Regnum 176.170

From www.fda.gov

Computed Descriptors

Download SDF
2D Structure
CID22947
IUPAC Name1,3-bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione
InChIInChI=1S/C7H12N2O4/c1-7(2)5(12)8(3-10)6(13)9(7)4-11/h10-11H,3-4H2,1-2H3
InChI KeyWSDISUOETYTPRL-UHFFFAOYSA-N
Canonical SMILESCC1(C(=O)N(C(=O)N1CO)CO)C
Molecular FormulaC7H12N2O4
WikipediaDMDM hydantoin

From Pubchem

Computed Properties

Property Name Property Value
Molecular Weight188.183
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Complexity251.0
CACTVS Substructure Key Fingerprint A A A D c c B j O A A A A A A A A A A A A A A A A A A A A W A A A A A A A A A A A A A A A A A A A A A A H g A A C A A A D I i B g A Y D A A M A A g A I A A E Q E A A A A A A A A A A A A A G I A A C A U A A A A C A U A A A I B y I A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area81.1
Monoisotopic Mass188.08
Exact Mass188.08
XLogP3None
XLogP3-AA-0.2
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count13
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem

ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.5603
Human Intestinal AbsorptionHIA+0.8320
Caco-2 PermeabilityCaco2-0.5984
P-glycoprotein SubstrateSubstrate0.5302
P-glycoprotein InhibitorNon-inhibitor0.8103
Non-inhibitor0.7993
Renal Organic Cation TransporterNon-inhibitor0.8950
Distribution
Subcellular localizationMitochondria0.5011
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8365
CYP450 2D6 SubstrateNon-substrate0.8393
CYP450 3A4 SubstrateNon-substrate0.6497
CYP450 1A2 InhibitorNon-inhibitor0.8932
CYP450 2C9 InhibitorNon-inhibitor0.8366
CYP450 2D6 InhibitorNon-inhibitor0.9046
CYP450 2C19 InhibitorNon-inhibitor0.7389
CYP450 3A4 InhibitorNon-inhibitor0.6562
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9608
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9759
Non-inhibitor0.9231
AMES ToxicityNon AMES toxic0.5558
CarcinogensNon-carcinogens0.7478
Fish ToxicityLow FHMT0.6130
Tetrahymena Pyriformis ToxicityHigh TPT0.6786
Honey Bee ToxicityLow HBT0.7066
BiodegradationNot ready biodegradable0.8710
Acute Oral ToxicityIII0.7695
Carcinogenicity (Three-class)Non-required0.5858

From admetSAR

ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-2.1062LogS
Caco-2 Permeability0.8419LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0056LD50, mol/kg
Fish Toxicity2.4380pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.0713pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of ExposureOral ; inhalation ; dermal
Mechanism of ToxicityDMDM hydantoin is a formaldehyde releaser. It is likely that formaldehyde toxicity occurs when intracellular levels saturate formaldehyde dehydrogenase activity, allowing the unmetabolized intact molecule to exert its effects. Formaldehyde is known to form cross links between protein and DNA and undergo metabolic incorporation into macromolecules (DNA, RNA, and proteins).
MetabolismFormaldehyde may be absorbed following inhalation, oral, or dermal exposure. It is an essential metabolic intermediate in all cells and is produced during the normal metabolism of serine, glycine, methionine, and choline and also by the demethylation of N-, S-, and O-methyl compounds. Exogenous formaldehyde is metabolized to formate by the enzyme formaldehyde dehydrogenase at the initial site of contact. After oxidation of formaldehyde to formate, the carbon atom is further oxidized to carbon dioxide or incorporated into purines, thymidine, and amino acids via tetrahydrofolatedependent one-carbon biosynthetic pathways. Formaldehyde is not stored in the body and is excreted in the urine (primarily as formic acid), incorporated into other cellular molecules, or exhaled as carbon dioxide.
Toxicity ValuesLD50: 2.0-3.65 g/kg (Oral, Rat)
Lethal Dose
Carcinogenicity (IARC Classification)1, carcinogenic to humans (for formaldehyde).
Minimum Risk Level
Health EffectsDMDM hydantoin releases formaldehyde, a known human carcinogen. (L962, L1896)
Treatment
Reference
  1. Hippe E, Olesen H, Skouby A: [Occurrence of antibodies against transcobalamin II in relation to the number of and the intervals between depot therapy with hydroxocobalamin]. Nord Med. 1970 Dec 3;84(49):1570.[5488577 ]
  2. de Groot AC, van Joost T, Bos JD, van der Meeren HL, Weyland JW: Patch test reactivity to DMDM hydantoin. Relationship to formaldehyde allergy. Contact Dermatitis. 1988 Apr;18(4):197-201.[3378426 ]

From T3DB

Taxonomic Classification

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassAzolidines
SubclassImidazolidines
Intermediate Tree NodesImidazolidinones - Imidazolidinediones
Direct ParentHydantoins
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
SubstituentsHydantoin - Alpha-amino acid or derivatives - N-acyl urea - Ureide - Dicarboximide - Carbonic acid derivative - Urea - Alkanolamine - Carboxylic acid derivative - Azacycle - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Organonitrogen compound - Organooxygen compound - Organic nitrogen compound - Aliphatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.

From ClassyFire