Sch 642305: a bicyclic 10-membered macrolide; bacterial DNA primase inhibitor produced by Penicillium verrucosum; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
sch 642305 : A macrocyclic lactone isolated from the fermentation broth of the fungal culture Penicillium verrucosum and has been shown to exhibit inhibitory activity against bacterial DNA primase enzyme. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 637324 |
| CHEMBL ID | 453428 |
| CHEBI ID | 66181 |
| MeSH ID | M0462618 |
| Synonym |
|---|
| (4s,8ar,12s,12ar)-12-hydroxy-4-methyl-4,5,6,7,8,8a,12,12a-octahydro-1h-3-benzoxecine-2,9-dione |
| 4-hydroxy-8-methyl-4a,5,8,9,10,11,12,12a-octahydro-4h-7-oxa-benzocyclodecene-1,6-dione |
| inchi=1/c14h20o4/c1-9-4-2-3-5-10-11(8-14(17)18-9)13(16)7-6-12(10)15/h6-7,9-11,13,16h,2-5,8h2,1h3/t9-,10+,11+,13-/m0/s |
| sch 642305 |
| 2h-3-benzoxecin-2,9(1h)-dione, 4,5,6,7,8,8a,12,12a-octahydro-12-hydroxy-4-methyl-, (4s,8ar,12s,12ar)- |
| rel-(4r,8as,12r,12as)-12-hydroxy-4-methyl-4,5,6,7,8,8a,12,12a-octahydro-2h-3-benzoxecine-2,9(1h)-dione |
| (4s,8ar,12s,12ar)-12-hydroxy-4-methyl-4,5,6,7,8,8a-hexahydro-1h-benzo[d]oxecine-2,9(12h,12ah)-dione |
| bdbm50250671 |
| chebi:66181 , |
| sch-642305 |
| CHEMBL453428 , |
| (+)-sch 642305 |
| (4s,8ar,12s,12ar)-12-hydroxy-4-methyl-4,5,6,7,8,8a,12,12a-octahydro-2h-3-benzoxecine-2,9(1h)-dione |
| 643747-04-0 |
| Q15424766 |
| DTXSID901045496 |
| PD127790 |
| Role | Description |
|---|---|
| Penicillium metabolite | Any fungal metabolite produced during a metabolic reaction in Penicillium. |
| EC 2.7.7.6 (RNA polymerase) inhibitor | An EC 2.7.7.* (nucleotidyltransferase) inhibitor that interferes with the action of RNA polymerase (EC 2.7.7.6). |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| macrocyclic lactone | Any lactone in which the cyclic carboxylic ester group forms a part of a cyclic macromolecule. |
| enone | An alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID356649 | Inhibition of Escherichia coli DNA primase after 1 hr by [3H]rNTPs incorporation assay | 2003 | Journal of natural products, Dec, Volume: 66, Issue:12 | Isolation and structure elucidation of Sch 642305, a novel bacterial DNA primase inhibitor produced by Penicillium verrucosum. |
| AID590651 | Cytotoxicity against human K562 cells assessed as inhibition of cell proliferation after 72 hrs by MTS assay | 2011 | Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8 | Biotransformation of natural compounds. Oxido-reduction of Sch-642305 by Aspergillus ochraceus ATCC 1009. |
| AID356650 | Antibacterial activity against Escherichia coli HS294 after 18 hrs by microtitre plate method | 2003 | Journal of natural products, Dec, Volume: 66, Issue:12 | Isolation and structure elucidation of Sch 642305, a novel bacterial DNA primase inhibitor produced by Penicillium verrucosum. |
| AID590650 | Cytotoxicity against human MDA-MB-231 cells assessed as inhibition of cell proliferation after 72 hrs by MTS assay | 2011 | Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8 | Biotransformation of natural compounds. Oxido-reduction of Sch-642305 by Aspergillus ochraceus ATCC 1009. |
| AID590648 | Antibacterial activity against Bacillus subtilis ATCC 6633 at 100 ug by disk inhibition zone method relative to gentamycin | 2011 | Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8 | Biotransformation of natural compounds. Oxido-reduction of Sch-642305 by Aspergillus ochraceus ATCC 1009. |
| AID590720 | Antibacterial activity against Escherichia coli ATCC 25922 at 100 ug by disk inhibition zone method relative to chloramphenicol | 2011 | Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8 | Biotransformation of natural compounds. Oxido-reduction of Sch-642305 by Aspergillus ochraceus ATCC 1009. |
| AID590649 | Antibacterial activity against Micrococcus luteus ATCC 10240 at 100 ug by disk inhibition zone method relative to chloramphenicol | 2011 | Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8 | Biotransformation of natural compounds. Oxido-reduction of Sch-642305 by Aspergillus ochraceus ATCC 1009. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 7 (58.33) | 29.6817 |
| 2010's | 4 (33.33) | 24.3611 |
| 2020's | 1 (8.33) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (11.87) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 3 (25.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 9 (75.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||