Dipyrithione

Details

• Internal ID: 3ea55e1c-6e79-4095-9908-6c758620f7b8
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > Pyridinium derivatives
• IUPAC Name: 1-oxido-2-[(1-oxidopyridin-1-ium-2-yl)disulfanyl]pyridin-1-ium
• SMILES (Canonical): C1=CC=[N+](C(=C1)SSC2=CC=CC=[N+]2[O-])[O-]
• SMILES (Isomeric): C1=CC=[N+](C(=C1)SSC2=CC=CC=[N+]2[O-])[O-]
• InChI: InChI=1S/C10H8N2O2S2/c13-11-7-3-1-5-9(11)15-16-10-6-2-4-8-12(10)14/h1-8H
• InChI Key: ZHDBTKPXEJDTTQ-UHFFFAOYSA-N
• Popularity: 46 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₈N₂O₂S₂
• Molecular Weight: 252.30 g/mol
• Exact Mass: 252.00271985 g/mol
• Topological Polar Surface Area (TPSA): 102.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.75
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• 3696-28-4
• 2,2'-DITHIOBIS(PYRIDINE-N-OXIDE)
• Omadine disulfide
• Bispyrithione
• OMDS
• pyrithione disulfide
• Dipiritiona
• Dipyrithionum
• 2,2-Dithiobis(pyridine-n-oxide)
• Omadine DS
• Bis(2-pyridyl-N-oxide) disulfide
• Bis(N-oxido-2-pyridyl) disulfide
• Pyrithione disulphide
• Bis(2-pyridine-N-oxide) disulfide
• Bis(2-pyridyl) disulfide di-N-oxide
• Bis(2-pyridyl-1-oxide) disulfide
• Dipyrithione [USAN:INN]
• Dipiritiona [INN-Spanish]
• Dipyrithionum [INN-Latin]
• 2,2'-Dithiobis(pyridine 1-oxide)
• 2,2'-Dithiodipyridine 1,1'-dioxide
• OSY 20
• EINECS 223-024-5
• NSC 84740
• NSC-84740
• 2,2'-Dithiodipyridine-1,1'-dioxide
• NSC 241716
• NSC-241716
• 1-oxido-2-[(1-oxidopyridin-1-ium-2-yl)disulfanyl]pyridin-1-ium
• BRN 0217725
• 2,2'-Dithiobis(pyridine 1,1'-dioxide)
• UNII-9L87N86R9A
• pyrion disulfide
• Pyridine, 2,2'-dithiobis-, 1,1'-dioxide
• Pyridine, 2,2'-dithiodi-, 1,1'-dioxide
• DTXSID1041897
• 9L87N86R9A
• 2,2'-Dithiobis(pyridine N-oxide)
• 2,2'-Thiobispyridine-1,1'-dioxide
• MFCD00006197
• 2,1'-dioxide
• 2,1'-dioxide)
• NCGC00164493-01
• NCGC00164493-02
• Pyridine, 2,2'-dithiobis- 1,1'-dioxide
• 5-21-02-00055 (Beilstein Handbook Reference)
• DTXCID9021897
• 2-[(1-oxidopyridin-1-ium-2-yl)disulfanyl]pyridin-1-ium-1-olate
• Pyridine,2'-dithiobis- 1,1'-dioxide
• Pyridine,2'-dithiodi-, 1,1'-dioxide
• Pyridine,2'-dithiobis-, 1,1'-dioxide
• CAS-3696-28-4
• 2,2'-Dithiobis(pyridine) 1,1'-dioxide
• C10H8N2O2S2
• Dipyrithione (USAN/INN)
• DIPYRITHIONE [INN]
• DIPYRITHIONE [USAN]
• BISPYRITHIONE [INCI]
• SCHEMBL21165
• DIPYRITHIONE [MART.]
• CHEMBL549473
• CHEBI:136010
• ZHDBTKPXEJDTTQ-UHFFFAOYSA-N
• HY-N8432
• NSC84740
• Tox21_112131
• 2.2/'-Dithiobis(pyridine-N-oxide)
• NSC241716
• NSC677437
• 2,2'-disulfanediyldipyridine 1-oxide
• AKOS015898887
• Tox21_112131_1
• DB11327
• AS-13849
• SY113495
• LS-131546
• CS-0144153
• FT-0634975
• 2,2-DITHIOBIS(PYRIDINE-N-OXIDE),97
• DI-2-PYRIDYL DISULFIDE 1,1'-DIOXIDE
• D03862
• H10998
• EN300-7384118
• Not available;2,2'-Dithiobis(pyridine-N-oxide)
• A857400
• SR-01000872605
• J-506839
• SR-01000872605-2
• Q17321248

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9658	96.58%
Caco-2	+	0.8064	80.64%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6823	68.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9347	93.47%
OATP1B3 inhibitior	+	0.9448	94.48%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7003	70.03%
P-glycoprotein inhibitior	-	0.9654	96.54%
P-glycoprotein substrate	-	0.9557	95.57%
CYP3A4 substrate	-	0.7263	72.63%
CYP2C9 substrate	-	0.8137	81.37%
CYP2D6 substrate	-	0.8424	84.24%
CYP3A4 inhibition	-	0.7382	73.82%
CYP2C9 inhibition	-	0.5885	58.85%
CYP2C19 inhibition	+	0.5827	58.27%
CYP2D6 inhibition	-	0.8835	88.35%
CYP1A2 inhibition	+	0.6385	63.85%
CYP2C8 inhibition	-	0.8934	89.34%
CYP inhibitory promiscuity	+	0.6553	65.53%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8028	80.28%
Carcinogenicity (trinary)	Non-required	0.5045	50.45%
Eye corrosion	-	0.9753	97.53%
Eye irritation	+	0.8429	84.29%
Skin irritation	-	0.6175	61.75%
Skin corrosion	-	0.9190	91.90%
Ames mutagenesis	-	0.8278	82.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.8544	85.44%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.7670	76.70%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.6023	60.23%
Acute Oral Toxicity (c)	III	0.6816	68.16%
Estrogen receptor binding	+	0.7147	71.47%
Androgen receptor binding	+	0.5485	54.85%
Thyroid receptor binding	+	0.5320	53.20%
Glucocorticoid receptor binding	+	0.7977	79.77%
Aromatase binding	+	0.6788	67.88%
PPAR gamma	+	0.8708	87.08%
Honey bee toxicity	-	0.9080	90.80%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.8900	89.00%
Fish aquatic toxicity	+	0.9063	90.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5514	P42858	Huntingtin	5011.9 nM	Potency	PMID: 22907036
CHEMBL1293235	P02545	Prelamin-A/C	112.2 nM; 112.2 nM	Potency; Potency	PMID: 24044895; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.15%	95.56%
CHEMBL240	Q12809	HERG	91.30%	89.76%
CHEMBL2581	P07339	Cathepsin D	86.09%	98.95%
CHEMBL2039	P27338	Monoamine oxidase B	84.34%	92.51%
CHEMBL3902	P09211	Glutathione S-transferase Pi	83.80%	93.81%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.43%	86.33%

Plants that contains it

• Allium stipitatum

Cross-Links

• PubChem: 3109
• NPASS: NPC135488
• ChEMBL: CHEMBL549473
• LOTUS: LTS0069291
• wikiData: Q17321248