(+)-Rugulosin
Basic information
- CAS
21884-45-7- Standard SMILES
Cc1cc(O)c2c(c1)C(=O)C13C(=C2O)C(=O)C2C(O)C1C1C(O)C3C(=O)C3=C(O)c4c(O)cc(C)cc4C(=O)C321- InChIKey
QFDPVUTXKUGISP-UHFFFAOYSA-N- Molecular formula
- C30H22O10
- Average molar mass
- 542.5 g/mol
- Monoisotopic mass
- 542.12129689
Overview
Rugulosin is a cyclic ketone and an organic polycyclic compound.
Names & identifiers
- Preferred name
- (+)-Rugulosin
- IUPAC
- 8,10,14,23,25,28-hexahydroxy-6,21-dimethyloctacyclo[14.11.1.02,11.02,15.04,9.013,17.017,26.019,24]octacosa-4(9),5,7,10,19(24),20,22,25-octaene-3,12,18,27-tetrone
- English name
- Rugulosin, (1S,1'S,2R,2'R,3S,3'S,9ar,9'ar)-
- Molecular formula
- C30H22O10
- Molecular weight
- 542.48968
Names & synonyms
23537-16-8Radicalisin(+)-RugulosinRUGULOSIN(+)21884-45-7NSC249990Rugulosin, (1S,1'S,2R,2'R,3S,3'S,9aR,9'aR)-NSC 160880Rugulosin - form(5aS,6R,13aS,14R,17S,18R,19R,20S)-1,7,9,15,17,20-Hexahydroxy-3,11-dimethyl-5H,6H-6,13a,5a,14-[1,2,3,4]butanetetraylcycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16(14H)-tetrone5H,6H-6,13a,5a,14-(1,2,3,4)Butanetetraylcycloocta(1,2-b:5,6-b')dinaphthalene-5,8,13,16(14H)-tetrone, 1,7,9,15,17,20-hexahydroxy-3,11-dimethyl-, (5aR-(5aR*,6S*,13aR*,14S*,17R*,18S*,19S*,20R*))-MFCD01684610
Show more names
(?)-Rugulosin(-)-Rugulosin5H,6H-6,13a,5a,14-[1,2,3,4]Butanetetraylcycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16(14H)-tetrone, 1,7,9,15,17,20-hexahydroxy-3,11-dimethyl-, [5aR-(5aR*,6S*,13aR*,14S*,17R*,18S*,19S*,20R*)]- (9CI)
NSC-160880NSC-2499905H,13a,5a,14-[1,2,3,4]Butanetetraylcycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16(14H)-tetrone, 1,7,9,15,17,20-hexahydroxy-3,11-dimethyl-5H,13a,5a,14-[1,2,3,4]Butanetetraylcycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16(14H)-tetrone, 1,7,9,15,17,20-hexahydroxy-3,11-dimethyl-, [5aS-(5aR*,6S*,13aR*,14S*,17R*,18S*,19S*,20R*)]-5H,6H-6,13a,5a,14-[1,2,3,4]Butanetetraylcycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16(14H)-tetrone, 1,7,9,15,17,20-hexahydroxy-3,11-dimethyl-, (5aS,6R,13aS,14R,17S,18R,19R,20S)-Rugulosin ((+) form)hexahydroxy(dimethyl)[?]tetroneSCHEMBL29723404
Properties
Computed structural properties
- XLogP
- 1
- Topological polar surface area
- 190 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 0
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 1,290
Physicochemical properties
- Boiling point
- 1009.4 · 1009.4±65.0 °C(Predicted)
- Density
- 1.87 · 1.87±0.1 g/cm3(Predicted)
- solubility
- DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble
- form
- A solid
- pka
- 4.2 · 4.20±1.00(Predicted)
Chemistry & industry
Applications
Uses(-)-Rugulosin is the less common optical isomer of the mycotoxin, (+)-rugulosin, which was first isolated from Myrothecium verrucaria in 1968. The isomers appear not to be co-produced but both occur widely in several fungal genera. (-)-Rugulosin has been shown to be antiviral. (-)Rugulosin is the less studied of the isomers and its role as a mycotoxin is implied rather than established. There are few comparative studies of the relative potency of the isomers.
Uses(-)-Rugulosin is the less common optical isomer of mycotoxin, shown to be antiviral.
Additional notes
DefinitionChEBI: Rugulosin is a cyclic ketone and an organic polycyclic compound.
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