Rocaglamide
| Internal ID | 531fff98-cc99-49b8-a963-cd62c2a39c12 |
| Taxonomy | Organoheterocyclic compounds > Benzofurans > Flavaglines |
| IUPAC Name | (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide |
| SMILES (Canonical) | CN(C)C(=O)C1C(C2(C(C1O)(C3=C(O2)C=C(C=C3OC)OC)O)C4=CC=C(C=C4)OC)C5=CC=CC=C5 |
| SMILES (Isomeric) | CN(C)C(=O)[C@@H]1[C@H]([C@]2([C@@]([C@@H]1O)(C3=C(O2)C=C(C=C3OC)OC)O)C4=CC=C(C=C4)OC)C5=CC=CC=C5 |
| InChI | InChI=1S/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1 |
| InChI Key | DAPAQENNNINUPW-IDAMAFBJSA-N |
| Popularity | 54 references in papers |
| Molecular Formula | C29H31NO7 |
| Molecular Weight | 505.60 g/mol |
| Exact Mass | 505.21005233 g/mol |
| Topological Polar Surface Area (TPSA) | 97.70 Ų |
| XlogP | 2.80 |
| Atomic LogP (AlogP) | 3.05 |
| H-Bond Acceptor | 7 |
| H-Bond Donor | 2 |
| Rotatable Bonds | 6 |
| 84573-16-0 |
| C29H31NO7 |
| MLS002701812 |
| CHEMBL438139 |
| CHEBI:66309 |
| Roc-A |
| NSC326408 |
| NSC-326408 |
| 1H-Cyclopenta(b)benzofuran-2-carboxamide, 2,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-, (1R,2R,3S,3aR,8bS)- |
| NSC 326408 |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9335 | 93.35% |
| Caco-2 | + | 0.5189 | 51.89% |
| Blood Brain Barrier | - | 0.6500 | 65.00% |
| Human oral bioavailability | - | 0.7429 | 74.29% |
| Subcellular localzation | Mitochondria | 0.6851 | 68.51% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.8837 | 88.37% |
| OATP1B3 inhibitior | + | 0.9370 | 93.70% |
| MATE1 inhibitior | - | 0.8600 | 86.00% |
| OCT2 inhibitior | - | 1.0000 | 100.00% |
| BSEP inhibitior | + | 0.9386 | 93.86% |
| P-glycoprotein inhibitior | + | 0.8849 | 88.49% |
| P-glycoprotein substrate | - | 0.6784 | 67.84% |
| CYP3A4 substrate | + | 0.6718 | 67.18% |
| CYP2C9 substrate | - | 0.7679 | 76.79% |
| CYP2D6 substrate | - | 0.7669 | 76.69% |
| CYP3A4 inhibition | - | 0.6780 | 67.80% |
| CYP2C9 inhibition | - | 0.7981 | 79.81% |
| CYP2C19 inhibition | - | 0.6509 | 65.09% |
| CYP2D6 inhibition | - | 0.8468 | 84.68% |
| CYP1A2 inhibition | - | 0.5829 | 58.29% |
| CYP2C8 inhibition | + | 0.6600 | 66.00% |
| CYP inhibitory promiscuity | - | 0.5999 | 59.99% |
| UGT catelyzed | + | 0.6000 | 60.00% |
| Carcinogenicity (binary) | - | 0.9300 | 93.00% |
| Carcinogenicity (trinary) | Non-required | 0.5138 | 51.38% |
| Eye corrosion | - | 0.9890 | 98.90% |
| Eye irritation | - | 0.8445 | 84.45% |
| Skin irritation | - | 0.8165 | 81.65% |
| Skin corrosion | - | 0.9381 | 93.81% |
| Ames mutagenesis | - | 0.5500 | 55.00% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.6449 | 64.49% |
| Micronuclear | + | 0.7400 | 74.00% |
| Hepatotoxicity | - | 0.6000 | 60.00% |
| skin sensitisation | - | 0.8909 | 89.09% |
| Respiratory toxicity | + | 0.6111 | 61.11% |
| Reproductive toxicity | + | 0.7111 | 71.11% |
| Mitochondrial toxicity | + | 0.7625 | 76.25% |
| Nephrotoxicity | + | 0.5357 | 53.57% |
| Acute Oral Toxicity (c) | III | 0.6122 | 61.22% |
| Estrogen receptor binding | + | 0.7763 | 77.63% |
| Androgen receptor binding | + | 0.7988 | 79.88% |
| Thyroid receptor binding | + | 0.6650 | 66.50% |
| Glucocorticoid receptor binding | + | 0.7292 | 72.92% |
| Aromatase binding | - | 0.5111 | 51.11% |
| PPAR gamma | + | 0.6620 | 66.20% |
| Honey bee toxicity | - | 0.8351 | 83.51% |
| Biodegradation | - | 0.8750 | 87.50% |
| Crustacea aquatic toxicity | + | 0.5551 | 55.51% |
| Fish aquatic toxicity | + | 0.9222 | 92.22% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL2052028 | P60842 | Eukaryotic initiation factor 4A-I |
4.7 nM |
IC50 |
via Super-PRED
|
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit |
2000 nM 75 nM 75 nM |
IC50 IC50 IC50 |
PMID: 19839614
via Super-PRED PMID: 20384315 |
| CHEMBL5533 | Q04206 | Nuclear factor NF-kappa-B p65 subunit |
70 nM 75 nM 75 nM 80 nM |
IC50 IC50 IC50 IC50 |
via Super-PRED
PMID: 21513293 PMID: 21428375 PMID: 19839614 |
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL240 | Q12809 | HERG | 96.43% | 89.76% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 95.99% | 95.56% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 95.09% | 91.11% |
| CHEMBL2716 | Q8WUI4 | Histone deacetylase 7 | 92.27% | 89.44% |
| CHEMBL4478 | Q00975 | Voltage-gated N-type calcium channel alpha-1B subunit | 89.75% | 97.14% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 89.47% | 86.33% |
| CHEMBL2581 | P07339 | Cathepsin D | 87.93% | 98.95% |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 | 87.08% | 91.19% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 86.83% | 96.00% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 86.15% | 99.17% |
| CHEMBL3091268 | Q92753 | Nuclear receptor ROR-beta | 85.47% | 95.50% |
| CHEMBL2373 | P21730 | C5a anaphylatoxin chemotactic receptor | 84.81% | 92.62% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 83.48% | 94.00% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 81.44% | 89.00% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 81.30% | 90.00% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 81.00% | 99.23% |
| CHEMBL1821 | P08173 | Muscarinic acetylcholine receptor M4 | 80.50% | 94.08% |
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.
| Aglaia basiphylla |
| Aglaia elaeagnoidea |
| Aglaia elliptica |
| Aglaia odorata |
| Aglaia rimosa |
| PubChem | 331783 |
| NPASS | NPC206061 |
| ChEMBL | CHEMBL438139 |
| LOTUS | LTS0031949 |
| wikiData | Q3437403 |