Basic information
- CAS
21884-44-6- Standard SMILES
Cc1cc(O)c2c(c1O)C(=O)C13C(=C2O)C(=O)C2C(O)C1C1C(O)C3C(=O)C3=C(O)c4c(O)cc(C)c(O)c4C(=O)C321- InChIKey
FAZDYVMEXQHRLI-UHFFFAOYSA-N- Molecular formula
- C30H22O12
- Average molar mass
- 574.5 g/mol
- Monoisotopic mass
- 574.11112613
Overview
Luteoskyrin is a cyclic ketone and an organic polycyclic compound.
Names & identifiers
- Preferred name
- Luteoskyrin
- IUPAC
- 5,8,10,14,20,23,25,28-octahydroxy-6,21-dimethyloctacyclo[14.11.1.02,11.02,15.04,9.013,17.017,26.019,24]octacosa-4,6,8,10,19,21,23,25-octaene-3,12,18,27-tetrone
- English name
- Rugulosin, 8,8'-dihydroxy-, (1S,1'S,2R,2'R,3S,3'S,9aR,9'aR)-
- Molecular formula
- C30H22O12
- Molecular weight
- 574.49
Names & synonyms
LUTEOSKYRIN(-)-Luteoskyrin8,8'-Dihydroxyrugulosin21884-44-6NSC160879Flavomycelin5,8,10,14,20,23,25,28-octahydroxy-6,21-dimethyloctacyclo[14.11.1.02,11.02,15.04,9.013,17.017,26.019,24]octacosa-4,6,8,10,19,21,23,25-octaene-3,12,18,27-tetroneRUGULOSIN, 8,8'-DEHYDROXY-Luteoskyrin, (-)-NSC-1608792,2',4,4'5,5',8,8'-Octahydroxy-2,2',3,3'-tetrahydro-7,7'-dimethyl-1,1'-bianthraquinone5H,6H-6,13a,5a,14-(1,2,3,4)Butanetetraylcycloocta(1,2-b:5,6-b')dinaphthalene-5,8,13,16(14H)-tetrone, 1,4,7,9,12,15,17,20-octahydroxy-3,11-dimethyl-
Show more names
LUTHEOSKIRINE(1S,1'S,2R,2'R,3S,3'S,9aR,9'aR)-8,8'-Dihydroxyrugulosin[1S,1'S,2R,2'R,3S,3'S,9aR,9'aR,(-)]-8,8'-DihydroxyrugulosinRugulosin, 8,8'-dihydroxy-, (1S,1'S,2R,2'R,3S,3'S,9aR,9'aR)-5H,6H-6,13a,5a,14-[1,2,3,4]Butanetetraylcycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16(14H)-tetrone, 1,4,7,9,12,15,17,20-octahydroxy-3,11-dimethyl-, (5aR,6S,13aR,14S,17R,18S,19S,20R)-
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 230 Ų
- Hydrogen bond donors
- 8
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 0
- Heavy atoms
- 42
- Formal charge
- 0
- Complexity
- 1,360
Physicochemical properties
- Melting point
- 278 °C · 278°C (rough estimate)
- Boiling point
- 555.89 °C · 555.89°C (rough estimate)
- Density
- 1.3474 · 1.3474 (rough estimate)
- refractive index
- 1.648 · 1.6480 (estimate)
- pka
- 4.2 · 4.20±1.00(Predicted)
- FDA UNII
- 3 VHC7Q8G9 · X3VHC7Q8G9
- IARC
- 3 · 3 (Vol. 10, Sup 7) 1987
- Hazardous Substances Data
- 21884 · 21884-44-6(Hazardous Substances Data)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Health EffectsLuteoskyrin is hepatotoxic and hepatocarcinogenic, causing hepatic disorders such as liver
cirrhosis and liver tumors. (A3069, A3070)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary
Luteoskyrin is hepatotoxic. It is thought that this is a result of its metabolic reduction to the semiquinone radical catalyzed by NADPH-dependent cytochrome reductases in the liver, leading to the generation of active oxygen species in redox systems. This causes the induction of lipid peroxidation, hepatocellular membrane damage, and elevation of serum transaminase activities, resultin in liver injuries. Luteoskyrin is also hepatocarcinogenic, possibly a result of its ability to induce DNA fragmentation. It is able to bind to DNA, forming chelate-complexes with nucleic acids and select metal ions. Luteoskyrin inhibits the replication, transcription and repair of DNA, which is at least partially because it inhibits RNA polymerase and ribonuclease H. (A2955, A3042, A3070, A3071, A3072)
Carcinogen Classification3, not classifiable as to its carcinogenicity to humans. (L135)
Safety data
- Hazardous Substances Data
- 21884-44-6(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Metabolism/MetabolitesLuteoskyrin accumulates selectively in the liver, with minor distribution to the serum and kidneys. In the liver it is reduced to its semiquinone radical by NADPH-dependent cytochrome reductases. (A3070,A3071)
Uses & manufacturing
UsesLuteoskyrin is a mycotoxin produced by the fungus Penicillium islandicum. It is known to be a storage mold contaminant of rice. (A3069)
Applications
Uses(-)-Luteoskyrin has a wide range of antibacterial activity, such as against malaria (with an IC50 of 0.51 μg/mL), tuberculosis (MIC of 6.25 μg/mL), and it also shows antibacterial effects (with MIC for Gram-positive bacteria ranging from 0.39 to 1.56 μg/mL, and for Gram-negative bacteria from 3.13 to 12.50 μg/mL), as well as antifungal activity (with MIC against plant pathogens ranging from 3.13 to 50μg/mL). (-)-Luteoskyrin exhibits cytotoxicity against NCI-H187 cells, with an IC50 range of 0.16–17.99 μg/mL[1].
Suppliers5 total
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
南通全益生物科技有限公司0513-66337626 18051384581 · [email protected]
上海超岚化工科技中心（原上海巢莱）0-2022843681 15618226720 · [email protected]
ATK CHEMICAL COMPANY LIMITED+undefined-21-51877795 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]
Related reactions
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Compound notes
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