Paraxanthine

Details

• Internal ID: 63e25a07-a874-481b-a9bc-7d12aa29214b
• Taxonomy: Organoheterocyclic compounds > Imidazopyrimidines > Purines and purine derivatives > Xanthines
• IUPAC Name: 1,7-dimethyl-3H-purine-2,6-dione
• SMILES (Canonical): CN1C=NC2=C1C(=O)N(C(=O)N2)C
• SMILES (Isomeric): CN1C=NC2=C1C(=O)N(C(=O)N2)C
• InChI: InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)
• InChI Key: QUNWUDVFRNGTCO-UHFFFAOYSA-N
• Popularity: 1,087 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇H₈N₄O₂
• Molecular Weight: 180.16 g/mol
• Exact Mass: 180.06472551 g/mol
• Topological Polar Surface Area (TPSA): 67.20 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -1.04
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 1,7-Dimethylxanthine
• 611-59-6
• p-Xanthine
• 1H-Purine-2,6-dione, 3,7-dihydro-1,7-dimethyl-
• 1,7-dimethyl-3H-purine-2,6-dione
• Xanthine, 1,7-dimethyl-
• Caffeine Impurity F
• 3,7-Dihydro-1,7-dimethyl-1H-purine-2,6-dione
• 1,7-dimethyl-Xanthine
• EINECS 210-271-9
• 1,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione
• NSC 400018
• NSC-400018
• BRN 0197907
• CHEMBL1158
• 1,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• DTXSID2052281
• UNII-Q3565Y41V7
• CHEBI:25858
• Q3565Y41V7
• 5-26-13-00554 (Beilstein Handbook Reference)
• PXT
• MFCD00005727
• Paraxanthine(72%)
• Spectrum2_001733
• Spectrum3_000774
• Spectrum4_001207
• Spectrum5_001506
• Lopac-D-5385
• PARAXANTHINE [INCI]
• Lopac0_000389
• BSPBio_002448
• KBioGR_001614
• MLS000859929
• DivK1c_000081
• SCHEMBL232702
• SPECTRUM2300170
• SPBio_001806
• SCHEMBL4651937
• DTXCID2030853
• HMS500E03
• KBio1_000081
• KBio3_001668
• NINDS_000081
• HMS2231K19
• HMS3261M19
• HMS3370A12
• Tox21_303803
• Tox21_500389
• BDBM50042210
• CCG-39489
• NSC400018
• Paraxanthine (1,7-Dimethylxanthine)
• 1,7-Dimethylxanthine, ~98%, solid
• AKOS015913484
• CS-W017214
• HY-W016498
• LP00389
• SDCCGSBI-0050376.P003
• IDI1_000081
• NCGC00015347-01
• NCGC00015347-02
• NCGC00015347-03
• NCGC00015347-04
• NCGC00015347-05
• NCGC00015347-06
• NCGC00015347-07
• NCGC00015347-09
• NCGC00093817-01
• NCGC00093817-02
• NCGC00093817-03
• NCGC00093817-04
• NCGC00261074-01
• NCGC00357087-01
• AS-64037
• CAFFEINE IMPURITY F [EP IMPURITY]
• CAS-611-59-6
• SMR000326790
• Eur J Pharmacol 179: 295 (1990)
• LS-101275
• 1H-Purine-2, 3,7-dihydro-1,7-dimethyl-
• 3-(4-METHOXY-1-NAPHTHYL)ACRYLICACID
• D5696
• EU-0100389
• FT-0632550
• FT-0673516
• D 5385
• D94772
• EN300-1666036
• A853055
• Q419223
• SR-01000075184
• 1,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione #
• 1,7-Dimethylxanthine 100 microg/mL in Acetonitrile
• SR-01000075184-1
• BRD-K24084088-001-02-2
• BRD-K24084088-001-06-3
• CAFFEINE MONOHYDRATE IMPURITY F [EP IMPURITY]
• Z1255430986
• 1,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione (Paraxanthine; 1,7-Dimethylxanthine)
• 1,7-DIMETHYL-3,7-DIHYDRO- 1H-PURINE-2,6-DIONE (Caffeine Impurity F), Pharmaceutical Secondary Standard; Certified Reference Material
• InChI=1/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	-	0.7505	75.05%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7079	70.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9695	96.95%
OATP1B3 inhibitior	+	0.9524	95.24%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9569	95.69%
BSEP inhibitior	-	0.9391	93.91%
P-glycoprotein inhibitior	-	0.9581	95.81%
P-glycoprotein substrate	-	0.8784	87.84%
CYP3A4 substrate	-	0.6193	61.93%
CYP2C9 substrate	-	0.6667	66.67%
CYP2D6 substrate	-	0.8746	87.46%
CYP3A4 inhibition	-	0.9616	96.16%
CYP2C9 inhibition	-	0.9933	99.33%
CYP2C19 inhibition	-	0.9895	98.95%
CYP2D6 inhibition	-	0.9827	98.27%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9877	98.77%
CYP inhibitory promiscuity	-	0.9956	99.56%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7077	70.77%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9155	91.55%
Skin irritation	-	0.8749	87.49%
Skin corrosion	-	0.9647	96.47%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6618	66.18%
Micronuclear	+	0.9600	96.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.9497	94.97%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.7440	74.40%
Acute Oral Toxicity (c)	II	0.7269	72.69%
Estrogen receptor binding	-	0.9442	94.42%
Androgen receptor binding	-	0.6508	65.08%
Thyroid receptor binding	-	0.6644	66.44%
Glucocorticoid receptor binding	-	0.7454	74.54%
Aromatase binding	-	0.7859	78.59%
PPAR gamma	-	0.9059	90.59%
Honey bee toxicity	-	0.9635	96.35%
Biodegradation	+	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	-	0.7784	77.84%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	631 nM; 631 nM; 631 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED
CHEMBL340	P08684	Cytochrome P450 3A4	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	3162.3 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	4.5 nM; 4.5 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5697	Q9GZT9	Egl nine homolog 1	95.52%	93.40%
CHEMBL2581	P07339	Cathepsin D	93.53%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.30%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.06%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.42%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.93%	94.00%
CHEMBL255	P29275	Adenosine A2b receptor	86.40%	98.59%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.92%	89.34%
CHEMBL3401	O75469	Pregnane X receptor	84.85%	94.73%
CHEMBL4208	P20618	Proteasome component C5	82.94%	90.00%
CHEMBL1781	P11387	DNA topoisomerase I	82.69%	97.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.14%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	82.04%	94.75%

Plants that contains it

• Citrus × aurantium
• Sinomenium acutum
• Stephania tetrandra

Cross-Links

• PubChem: 4687
• NPASS: NPC47936
• ChEMBL: CHEMBL1158
• LOTUS: LTS0149000
• wikiData: Q419223