7-Methylxanthine

Details

• Internal ID: 320ab996-44e0-4183-b715-bcbae5597c34
• Taxonomy: Organoheterocyclic compounds > Imidazopyrimidines > Purines and purine derivatives > Xanthines
• IUPAC Name: 7-methyl-3H-purine-2,6-dione
• SMILES (Canonical): CN1C=NC2=C1C(=O)NC(=O)N2
• SMILES (Isomeric): CN1C=NC2=C1C(=O)NC(=O)N2
• InChI: InChI=1S/C6H6N4O2/c1-10-2-7-4-3(10)5(11)9-6(12)8-4/h2H,1H3,(H2,8,9,11,12)
• InChI Key: PFWLFWPASULGAN-UHFFFAOYSA-N
• Popularity: 286 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₆N₄O₂
• Molecular Weight: 166.14 g/mol
• Exact Mass: 166.04907545 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.05
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 552-62-5
• Heteroxanthine
• Heteroxanthin
• 7-Methylxanthin
• 2,6-Dihydroxy-7-methylpurine
• 7-Methyl-1H-purine-2,6(3H,7H)-dione
• Xanthine, 7-methyl-
• 7-methyl-3H-purine-2,6-dione
• 1H-Purine-2,6-dione, 3,7-dihydro-7-methyl-
• 3,7-Dihydro-7-methyl-1H-purine-2,6-dione
• 7-methyl-3,7-dihydro-1H-purine-2,6-dione
• methyl xanthine
• NSC 7861
• CCRIS 5818
• NSC-7861
• EINECS 209-019-0
• MFCD00037979
• UNII-E9M81NJM6G
• E9M81NJM6G
• 7-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• CHEMBL321248
• CHEBI:48991
• 7-methyl xanthine
• 7-MethylX
• 3,3-Difluorobenzophenone
• 7-Methyl-2,6-dioxypurin
• D04RKW
• METHYLXANTHINE, 7-
• SCHEMBL235130
• METHYL XANTHINE [INCI]
• 7-MX
• 7-methyl-7H-purine-2,6-diol
• BDBM82522
• DTXSID60203696
• NSC7861
• PDSP1_001040
• PDSP2_001024
• WLN: T56 BN DN FMVMVJ B1
• AKOS015903147
• CS-W017879
• HY-W017163
• 1H-Purine-2, 3,7-dihydro-7-methyl-
• 7-Methylxanthine, >=98.0% (HPLC)
• AS-56812
• CAS_552-62-5
• PD055547
• LS-162545
• FT-0672370
• Adenosine receptor antagonist (myopia), Trier
• EN300-393798
• 2-hydroxy-7-methyl-6,7-dihydro-1H-purin-6-one
• Q27121426
• InChI=1/C6H6N4O2/c1-10-2-7-4-3(10)5(11)9-6(12)8-4/h2H,1H3,(H2,8,9,11,12

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9890	98.90%
Caco-2	-	0.8395	83.95%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6189	61.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9727	97.27%
OATP1B3 inhibitior	+	0.9494	94.94%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9343	93.43%
P-glycoprotein inhibitior	-	0.9760	97.60%
P-glycoprotein substrate	-	0.8683	86.83%
CYP3A4 substrate	-	0.6886	68.86%
CYP2C9 substrate	-	0.6667	66.67%
CYP2D6 substrate	-	0.8746	87.46%
CYP3A4 inhibition	-	0.9327	93.27%
CYP2C9 inhibition	-	0.9702	97.02%
CYP2C19 inhibition	-	0.9351	93.51%
CYP2D6 inhibition	-	0.9382	93.82%
CYP1A2 inhibition	-	0.8316	83.16%
CYP2C8 inhibition	-	0.9927	99.27%
CYP inhibitory promiscuity	-	0.9907	99.07%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6995	69.95%
Eye corrosion	-	0.9814	98.14%
Eye irritation	-	0.5071	50.71%
Skin irritation	-	0.8478	84.78%
Skin corrosion	-	0.9576	95.76%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6088	60.88%
Micronuclear	+	0.9600	96.00%
Hepatotoxicity	+	0.8375	83.75%
skin sensitisation	-	0.9356	93.56%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.6817	68.17%
Acute Oral Toxicity (c)	III	0.4984	49.84%
Estrogen receptor binding	-	0.9460	94.60%
Androgen receptor binding	-	0.7108	71.08%
Thyroid receptor binding	-	0.6831	68.31%
Glucocorticoid receptor binding	-	0.8424	84.24%
Aromatase binding	-	0.6903	69.03%
PPAR gamma	-	0.8605	86.05%
Honey bee toxicity	-	0.9604	96.04%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	-	0.9090	90.90%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3129	Q9Y2T3	Guanine deaminase	5550 nM	Ki	PMID: 20716488

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	90.14%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.05%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.99%	96.09%
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	89.94%	95.72%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.90%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.14%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	85.72%	94.75%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.49%	89.34%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.00%	99.23%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	84.01%	93.10%
CHEMBL3401	O75469	Pregnane X receptor	83.70%	94.73%
CHEMBL1781	P11387	DNA topoisomerase I	82.23%	97.00%
CHEMBL255	P29275	Adenosine A2b receptor	81.43%	98.59%
CHEMBL4208	P20618	Proteasome component C5	80.28%	90.00%

Plants that contains it

• Beta vulgaris
• Coffea arabica
• Theobroma cacao

Cross-Links

• PubChem: 68374
• NPASS: NPC248007
• ChEMBL: CHEMBL321248
• LOTUS: LTS0192607
• wikiData: Q27121426