Gs-39783

Details

• Internal ID: 757d11e4-3481-4661-aaa1-952287ef25a5
• Taxonomy: Organosulfur compounds > Thioethers > Aryl thioethers
• IUPAC Name: 4-N,6-N-dicyclopentyl-2-methylsulfanyl-5-nitropyrimidine-4,6-diamine
• SMILES (Canonical): CSC1=NC(=C(C(=N1)NC2CCCC2)[N+](=O)[O-])NC3CCCC3
• SMILES (Isomeric): CSC1=NC(=C(C(=N1)NC2CCCC2)[N+](=O)[O-])NC3CCCC3
• InChI: InChI=1S/C15H23N5O2S/c1-23-15-18-13(16-10-6-2-3-7-10)12(20(21)22)14(19-15)17-11-8-4-5-9-11/h10-11H,2-9H2,1H3,(H2,16,17,18,19)
• InChI Key: GSGVDKOCBKBMGG-UHFFFAOYSA-N
• Popularity: 92 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₃N₅O₂S
• Molecular Weight: 337.40 g/mol
• Exact Mass: 337.15724617 g/mol
• Topological Polar Surface Area (TPSA): 121.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 3.82
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• GS 39783
• N4,N6-dicyclopentyl-2-(methylthio)-5-nitropyrimidine-4,6-diamine
• GS39783
• GS-39783
• HD3T22A5DM
• 4-N,6-N-dicyclopentyl-2-methylsulfanyl-5-nitropyrimidine-4,6-diamine
• N,N'-Dicyclopentyl-2-(methylthio)-5- nitro-4,6-pyrimidinediamine
• N,N'-Dicyclopentyl-2-(methylthio)-5-nitro-4,6-pyrimidinediamine
• N4,N6-Dicyclopentyl-2-(methylthio)-5-nitro-4,6-pyrimidinediamine
• N,N'-Dicyclopentyl-2-methylsulfanyl-5-nitro-pyrimidine-4,6-diamine
• N~4~,N~6~-dicyclopentyl-2-(methylsulfanyl)-5-nitropyrimidine-4,6-diamine
• Pseudoephedrine,(+)
• NCGC00025340-01
• Tocris-2001
• UNII-HD3T22A5DM
• CHEMBL392394
• GTPL5446
• SCHEMBL3578392
• BDBM86283
• C15H23N5O2S
• CHEBI:93326
• DTXSID30424992
• GSGVDKOCBKBMGG-UHFFFAOYSA-N
• HMS3268D17
• HMS3413A11
• HMS3677A11
• PDSP1_000401
• PDSP2_000399
• AKOS024456904
• AKOS040745200
• SB58749
• NCGC00025340-02
• CAS_345-78-8
• CAS_39069-52-8
• HY-103475
• GS39783, >=98% (HPLC)
• SR-01000597525
• Q5514522
• SR-01000597525-1
• BRD-K75478907-001-01-5
• 4,6-Pyrimidinediamine, N4,N6-dicyclopentyl-2-(methylthio)-5-nitro-
• 4-N,6-N-dicyclopentyl-2-(methylsulfanyl)-5-nitropyrimidine-4,6-diamine
• QDA

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9656	96.56%
Caco-2	-	0.6860	68.60%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.4487	44.87%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.9574	95.74%
OATP1B3 inhibitior	+	0.9394	93.94%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.7810	78.10%
P-glycoprotein inhibitior	-	0.7132	71.32%
P-glycoprotein substrate	-	0.8411	84.11%
CYP3A4 substrate	-	0.5050	50.50%
CYP2C9 substrate	-	0.6162	61.62%
CYP2D6 substrate	-	0.8650	86.50%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	+	0.8948	89.48%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.8186	81.86%
CYP inhibitory promiscuity	+	0.5873	58.73%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.4204	42.04%
Eye corrosion	-	0.9754	97.54%
Eye irritation	-	0.7320	73.20%
Skin irritation	-	0.6648	66.48%
Skin corrosion	-	0.9191	91.91%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7693	76.93%
Micronuclear	+	0.9600	96.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.7459	74.59%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.7191	71.91%
Acute Oral Toxicity (c)	III	0.5333	53.33%
Estrogen receptor binding	+	0.6478	64.78%
Androgen receptor binding	+	0.6205	62.05%
Thyroid receptor binding	+	0.6531	65.31%
Glucocorticoid receptor binding	-	0.5052	50.52%
Aromatase binding	+	0.5370	53.70%
PPAR gamma	+	0.6219	62.19%
Honey bee toxicity	-	0.9347	93.47%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	-	0.5197	51.97%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3356	P05177	Cytochrome P450 1A2	3981.07 nM	AC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	5011.87 nM	AC50	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	1995.26 nM	AC50	via CMAUP
CHEMBL2111463	Q9UBS5	GABA-B receptor	741.31 nM	EC50	via Super-PRED
CHEMBL2064	Q9UBS5	GABA-B receptor 1	79.43 nM	EC50	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	891.3 nM; 891.3 nM	Potency; Potency	via Super-PRED; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	96.65%	92.88%
CHEMBL3038469	P24941	CDK2/Cyclin A	93.41%	91.38%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	93.26%	98.99%
CHEMBL240	Q12809	HERG	93.10%	89.76%
CHEMBL5408	Q9UHD2	Serine/threonine-protein kinase TBK1	91.83%	90.48%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	88.76%	80.96%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	88.61%	83.10%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.45%	99.23%
CHEMBL3055	P50613	Cyclin-dependent kinase 7	87.80%	81.88%
CHEMBL4660	P28907	Lymphocyte differentiation antigen CD38	87.40%	95.27%
CHEMBL308	P06493	Cyclin-dependent kinase 1	87.35%	91.73%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.18%	93.03%
CHEMBL221	P23219	Cyclooxygenase-1	86.17%	90.17%
CHEMBL230	P35354	Cyclooxygenase-2	84.48%	89.63%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.49%	91.24%
CHEMBL4070	P19784	Casein kinase II alpha (prime)	82.09%	91.67%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.73%	85.30%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.96%	93.10%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	80.46%	98.24%

Plants that contains it

• Ephedra equisetina
• Ephedra intermedia
• Ephedra sinica

Cross-Links

• PubChem: 6604928
• NPASS: NPC293799
• ChEMBL: CHEMBL392394