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23537-16-8

23537-16-8 Structure

23537-16-8 Structure
IdentificationBack Directory
[Name]

RUGULOSIN
[CAS]

23537-16-8
[Synonyms]

RUGULOSIN
Nsc160880
NSC 249990
Rugulosin A
(+)-RUGULOSIN
(+)-Rugulosin
(+)-(1S,1'S,2R,2'R,3S,3'S,9AR,9'AR)-RUGULOSIN
(+)-Rugulosin, (1S,1S,2R,2R,3S,3S,9aR,9aR)-Rugulosin, (2R,2R)-Rugulosin
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-
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)-
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-(5ar*,6S*,13ar*,14S*,17R*,18S*,19S*,20R*)]-
[Molecular Formula]

C30H22O10
[MDL Number]

MFCD01684610
[MOL File]

23537-16-8.mol
[Molecular Weight]

542.49
Chemical PropertiesBack Directory
[Melting point ]

293℃ (decomposition)
[Boiling point ]

535.95°C (rough estimate)
[density ]

1.3164 (rough estimate)
[refractive index ]

1.5376 (estimate)
[storage temp. ]

Store at -20°C
[solubility ]

DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble
[form ]

A solid
[pka]

4.20±1.00(Predicted)
[IARC]

3 (Vol. 40, Sup 7) 1987
[EPA Substance Registry System]

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)- (23537-16-8)
Safety DataBack Directory
[HS Code ]

29419000
Hazard InformationBack Directory
[Description]

(+)-Rugulosin is a pigment and mycotoxin produced by certain fungi. It inhibits HIV-1 integrase activity with IC50 values of 19 and 25 μM in coupled and strand transfer assays, respectively. It also inhibits ribonuclease H in rat liver by 83% at a concentration of 157 μM and ribonucleases H1, H2, and H3 in T. pyriformis by 100, 99, and 100%, respectively, at a concentration of 313 μM. (+)-Rugulosin leads to hepatic injury and liver cell hyperplasia in mice when administered in the diet. It is cytotoxic to insect cells but not mammalian C6/36, L929, and HepG2 cells (ID50s = 1.2, >200, 23.7, and >200 μg/ml, respectively).
[Uses]

(+)-Rugulosin is an intense yellow pigment produced by some species of Penicillium, Aspergillus and the fungal symbiotants of some lichens. (+)-Rugulosin shows antibacterial and insecticidal activity and has found application as a bioinsecticide, notably as the active secondary metabolite in endophytic fungi of seedlings.
[Uses]

Rugulosin (+ form) is an intense yellow pigment produced by Penicillium and Aspergillus.
[Definition]

ChEBI: Rugulosin is a cyclic ketone and an organic polycyclic compound.
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