Caffeine
| Internal ID | 2186e48a-74a0-426d-8a3a-f1c93614ed34 |
| Taxonomy | Organoheterocyclic compounds > Imidazopyrimidines > Purines and purine derivatives > Xanthines |
| IUPAC Name | 1,3,7-trimethylpurine-2,6-dione |
| SMILES (Canonical) | CN1C=NC2=C1C(=O)N(C(=O)N2C)C |
| SMILES (Isomeric) | CN1C=NC2=C1C(=O)N(C(=O)N2C)C |
| InChI | InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3 |
| InChI Key | RYYVLZVUVIJVGH-UHFFFAOYSA-N |
| Popularity | 65,838 references in papers |
| 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 |
| 58-08-2 |
| Guaranine |
| 1,3,7-Trimethylxanthine |
| Methyltheobromine |
| Theine |
| Thein |
| Cafeina |
| Koffein |
| Mateina |
| Alert-pep |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9931 | 99.31% |
| Caco-2 | - | 0.5986 | 59.86% |
| Blood Brain Barrier | + | 1.0000 | 100.00% |
| Human oral bioavailability | + | 0.9429 | 94.29% |
| Subcellular localzation | Mitochondria | 0.7450 | 74.50% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.9644 | 96.44% |
| OATP1B3 inhibitior | + | 0.9513 | 95.13% |
| MATE1 inhibitior | - | 1.0000 | 100.00% |
| OCT2 inhibitior | - | 0.9569 | 95.69% |
| BSEP inhibitior | - | 0.9760 | 97.60% |
| P-glycoprotein inhibitior | - | 0.9176 | 91.76% |
| P-glycoprotein substrate | - | 0.9451 | 94.51% |
| CYP3A4 substrate | - | 0.5766 | 57.66% |
| 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 | - | 0.9862 | 98.62% |
| 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 | - | 0.9515 | 95.15% |
| Skin irritation | - | 0.8721 | 87.21% |
| Skin corrosion | - | 0.9639 | 96.39% |
| Ames mutagenesis | - | 0.8800 | 88.00% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.7428 | 74.28% |
| Micronuclear | + | 0.9300 | 93.00% |
| Hepatotoxicity | - | 0.8250 | 82.50% |
| 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 | - | 0.5640 | 56.40% |
| Acute Oral Toxicity (c) | II | 0.7405 | 74.05% |
| Estrogen receptor binding | - | 0.9466 | 94.66% |
| Androgen receptor binding | - | 0.8186 | 81.86% |
| Thyroid receptor binding | - | 0.6892 | 68.92% |
| Glucocorticoid receptor binding | - | 0.7965 | 79.65% |
| Aromatase binding | - | 0.8341 | 83.41% |
| PPAR gamma | - | 0.9152 | 91.52% |
| Honey bee toxicity | - | 0.9366 | 93.66% |
| Biodegradation | + | 0.9250 | 92.50% |
| Crustacea aquatic toxicity | + | 0.6900 | 69.00% |
| Fish aquatic toxicity | - | 0.7597 | 75.97% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL220 | P22303 | Acetylcholinesterase |
7250 nM |
IC50 |
PMID: 23791077
|
| CHEMBL226 | P30542 | Adenosine A1 receptor |
44900 nM 44900 nM 44900 nM 44900 nM 44000 nM |
Ki Ki Ki Ki Ki |
PMID: 24139167
PMID: 24139167 PMID: 24164628 PMID: 21664729 PMID: 23602401 |
| CHEMBL251 | P29274 | Adenosine A2a receptor |
20472 nM |
IC50 |
via CMAUP
|
| CHEMBL255 | P29275 | Adenosine A2b receptor |
20500 nM 33800 nM 20500 nM 33800 nM 33800 nM 10400 nM 33800 nM 10400 nM 33800 nM 10400 nM |
Ki Ki Ki Ki Ki Ki Ki Ki Ki Ki |
PMID: 21664729
PMID: 24139167 PMID: 24164628 PMID: 24139167 PMID: 26824742 PMID: 20537438 PMID: 20188574 PMID: 19569717 PMID: 19569717 PMID: 12014951 |
| CHEMBL256 | P0DMS8 | Adenosine A3 receptor |
13300 nM 13300 nM 13300 nM |
Ki Ki Ki |
PMID: 12139454
PMID: 24139167 PMID: 24139167 |
| CHEMBL3129 | Q9Y2T3 | Guanine deaminase |
10200 nM |
Ki |
PMID: 20716488
|
| CHEMBL240 | Q12809 | HERG |
4897.79 nM |
IC50 |
PMID: 21185626
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 93.40% | 95.56% |
| CHEMBL2581 | P07339 | Cathepsin D | 92.88% | 98.95% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 92.33% | 96.09% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 89.72% | 94.00% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 85.59% | 85.14% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 83.47% | 94.73% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 82.15% | 86.33% |
| CHEMBL3864 | Q06124 | Protein-tyrosine phosphatase 2C | 81.41% | 94.42% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
To see more specific details click the taxa you are interested in.
To see more specific details click the taxa you are interested in.