Compound: Viridicatumtoxin
SMILES: O=C1c2c(O)c3c(O)cc(OC)c4c3c(c2[C@H](O)[C@@]5([C@@]1(O)C(=O)C(=C(O)C5)C(=O)N)O)C[C@@]64C(=CCCC6(C)C)C
InChIKey: SUWQGLGDFGHZNH-WBWZXODPSA-N
Synonyms: Viridicatumtoxin, 39277-41-3, VIRIDITOXIN (FORMERLY), NSC 159628, S8N62PLU21, NSC-159628, (3'S,4'S,6S,9'S)-3',4',8',9',12',14'-hexahydroxy-16'-methoxy-1,5,5-trimethyl-6',10'-dioxospiro[cyclohexene-6,18'-pentacyclo[11.6.1.02,11.04,9.017,20]icosa-1(20),2(11),7,12,14,16-hexaene]-7'-carboxamide, SC 28762, UNII-S8N62PLU21, viridicatumtoxin A, BRN 2934660, CHEMBL1984811, SCHEMBL17340089, SCHEMBL29426345, CHEBI:85616, DTXSID20893991, SID436556, NCI60_001174, NS00094937, Q27158664, Q63392839, (1S,7'aS,11'aS,12'S)-5',6',7'a,10',11'a,12'-Hexahydroxy-3'-methoxy-2,6,6-trimethyl-7',8'-dioxo-7',7'a,8',11',11'a,12'-hexahydro-1'H-spiro[cyclohex-2-ene-1,2'-cyclopenta[de]tetracene]-9'-carboxamide, (1S,7a'S,11a'R)-5',6',7a',10',11a'-Pentahydroxy-3'-methoxy-2,6,6-trimethyl-7',8',12'-trioxo-7',7a',8',11',11a',12'-hexahydro-1'H-spiro[cyclohex-2-ene-1,2'-cyclopenta[de]tetracene]-9'-carboxamide, (1S,7a'S,11a'S,12'S)-5',6',7a',10',11a',12'-hexahydroxy-3'-methoxy-2,6,6-trimethyl-7',8'-dioxo-7',7a',8',11',11a',12'-hexahydro-1'H-spiro[cyclohex-2-ene-1,2'-cyclopenta[de]tetracene]-9'-carboxamide, (8,3-c]pyran)-3,3'-diacetic acid, 3,3',4,4'-tetrahydro-9,9',10,10'-tetrahydroxy-7,7'-dimethoxy-1,1'-dioxo-, dimethyl ester, Spiro(2-cyclohexene-1,2'(1'H)-cyclopenta(de)naphthacene)-9'-carboxamide, 7',7'a,8',11',11'a,12'-hexahydro-5',6',7'a,10',11'a,12'-hexahydroxy-3'-methoxy-2,6,6-trimethyl-7',8'-dioxo-, (2'alpha,7'abeta,11'abeta,12'beta)-(-)-, Spiro[2-cyclohexene-1, 7',7'a,8',11',11'a,12'-hexahydro-5',6',7'a,10',11'a,12'-hexahydroxy-3'-methoxy-2,6,6-trimethyl-7',8'-dioxo-, (2'.alpha.,7'a.beta.,11'a.beta.,12'.beta.)-(-)-
Theoretical properties:
molecular_formula: C30H31NO10
molecular_weight: 565.6 g/mol
exact_mass: 565.19479619 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 7
hydrogen_bond_acceptor_count: 10
rotatable_bond_count: 2
heavy_atom_count: 41
topological_polar_surface_area: 208 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Viridicatumtoxin is a tetracycline-like polyketide antibiotic that is produced by several species of Penicillium and Aspergillus. It has a role as an antimicrobial agent, an antineoplastic agent, a fungal metabolite and an EC 2.5.1.31 {ditrans,polycis-undecaprenyl-diphosphate synthase [(2E,6E)-farnesyl-diphosphate specific]} inhibitor. It is a tertiary alpha-hydroxy ketone, a primary carboxamide, a polyketide, a polyphenol, a tertiary alcohol, a spiro compound, an enol, an aromatic ether, a secondary alcohol, a cyclic ketone, an enone, an enamide, an organic polycyclic compound and an aromatic ketone.
chebi: A tetracycline-like polyketide antibiotic that is produced by several species of <em>Penicillium</em> and <em>Aspergillus</em>.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Viridicatumtoxin A (also simply called viridicatumtoxin) is a fungus-derived tetracycline-like antibiotic, whose chemical structure was determined in 1976. It is found in Penicillium viridicatum, Penicillium aethiopicum, among other fungi.
Like viridicatumtoxin B, viridicatumtoxin A inhibits growth of Staphylococcus aureus, including methicillin resistant S. aureus and quinolone-resistant S. aureus, with an activity 8 to 64 times greater than that of tetracycline.