Isocaffeine

Details

• Internal ID: 4c13a5e6-3319-43d0-bf3b-772740065f51
• Taxonomy: Organoheterocyclic compounds > Imidazopyrimidines > Purines and purine derivatives > Xanthines
• IUPAC Name: 1,3,9-trimethylpurine-2,6-dione
• SMILES (Canonical): CN1C=NC2=C1N(C(=O)N(C2=O)C)C
• SMILES (Isomeric): CN1C=NC2=C1N(C(=O)N(C2=O)C)C
• InChI: InChI=1S/C8H10N4O2/c1-10-4-9-5-6(10)11(2)8(14)12(3)7(5)13/h4H,1-3H3
• InChI Key: LPHGQDQBBGAPDZ-UHFFFAOYSA-N
• Popularity: 26 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₀N₄O₂
• Molecular Weight: 194.19 g/mol
• Exact Mass: 194.08037557 g/mol
• Topological Polar Surface Area (TPSA): 58.40 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -1.03
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 519-32-4
• 1,3,9-Trimethylxanthine
• 1,3,9-trimethyl-3,9-dihydro-1H-purine-2,6-dione
• 1,3,9-trimethylpurine-2,6-dione
• Caffeine Impurity C (Isocaffeine)
• ISOCAFFIENE
• N4HG7T2QGW
• 3,9-Dihydro-1,3,9-trimethyl-1H-purine-2,6-dione
• CHEMBL74063
• 1H-Purine-2,6-dione, 3,9-dihydro-1,3,9-trimethyl-
• MLS002639222
• NSC-28332
• 1,3,9-Trimethyl-3,9-dihydro-purine-2,6-dione
• 1,3,9-Trimethyl-3,9-dihydro-1H-purine-2,6-dione (Isocaffeine)
• Isocoffein
• Caffeine Impurity C
• EINECS 208-267-7
• MFCD00022834
• NSC 28332
• 1,9-Trimethylxanthine
• UNII-N4HG7T2QGW
• 9-METHYLTHEOPHYLLINE
• 1,3,9-trimethyl-1H-purine-2,6(3H,9H)-dione
• SCHEMBL515995
• DTXSID70199859
• LPHGQDQBBGAPDZ-UHFFFAOYSA-N
• 1,3,9-trimethyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione
• HMS3079B15
• NSC28332
• BDBM50291815
• PDSP1_000325
• PDSP2_000323
• AKOS006274028
• CAFFEINE IMPURITY C [EP IMPURITY]
• SMR001548669
• FT-0632273
• E75853
• 1H-Purine-2, 3,9-dihydro-1,3,9-trimethyl-
• EN300-8589303
• 1,3,9-Trimethylxanthine, >=98% (HPLC), solid
• Q1674397
• W-202958
• CAFFEINE MONOHYDRATE IMPURITY C [EP IMPURITY]
• Z1198147847
• 1,3,9-TRIMETHYL-3,9-DIHYDRO -1H-PURINE-2,6-DIONE (Caffeine Impurity C), Pharmaceutical Secondary Standard; Certified Reference Material
• Caffeine Imp. C (EP); 1,3,9-Trimethyl-3,9-dihydro-1H-purine-2,6-dione; Isocaffeine; Caffeine Impurity C

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9931	99.31%
Caco-2	-	0.5502	55.02%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	+	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7450	74.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9664	96.64%
OATP1B3 inhibitior	+	0.9513	95.13%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9569	95.69%
BSEP inhibitior	-	0.9027	90.27%
P-glycoprotein inhibitior	-	0.9501	95.01%
P-glycoprotein substrate	-	0.9480	94.80%
CYP3A4 substrate	-	0.5898	58.98%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	-	0.8608	86.08%
CYP3A4 inhibition	-	0.9618	96.18%
CYP2C9 inhibition	-	0.9906	99.06%
CYP2C19 inhibition	-	0.9927	99.27%
CYP2D6 inhibition	-	0.9836	98.36%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.9868	98.68%
CYP inhibitory promiscuity	-	0.9924	99.24%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6936	69.36%
Eye corrosion	-	0.9849	98.49%
Eye irritation	-	0.8860	88.60%
Skin irritation	-	0.8721	87.21%
Skin corrosion	-	0.9639	96.39%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4512	45.12%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.9435	94.35%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	II	0.7405	74.05%
Estrogen receptor binding	-	0.9196	91.96%
Androgen receptor binding	-	0.8701	87.01%
Thyroid receptor binding	-	0.6896	68.96%
Glucocorticoid receptor binding	-	0.8115	81.15%
Aromatase binding	-	0.7044	70.44%
PPAR gamma	-	0.8291	82.91%
Honey bee toxicity	-	0.9352	93.52%
Biodegradation	+	0.6000	60.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	-	0.7597	75.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.32%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.19%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.33%	93.40%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.96%	94.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	85.94%	94.42%
CHEMBL2581	P07339	Cathepsin D	85.40%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.28%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	82.41%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.02%	99.23%

Plants that contains it

• Murraya paniculata

Cross-Links

• PubChem: 1326
• LOTUS: LTS0083913
• wikiData: Q1674397