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(-)-Siccanin

(-)-Siccanin structure

CAS No:
22733-60-4
Formula:
C22H30O3
Chemical Name:
(-)-Siccanin
Synonyms:
1H,11bH,13H-Benzo[a]furo[2,3,4-mn]xanthen-11-ol,2,3,4,4a,5,6,6a,13b-octahydro-4,4,6a,9-tetramethyl-,(4aS,6aS,11bR,13aS,13bS)-;13H-Benzo[a]furo[2,3,4-mn]xanthen-11-ol,1,2,3,4,4a,5,6,6a,11b,13b-decahydro-4,4,6a,9-tetramethyl-;Siccanin;13H-Benzo[a]furo[2,3,4-mn]xanthen-11-ol,1,2,3,4,4a,5,6,6a,11b,13b-decahydro-4,4,6a,9-tetramethyl-,[4aS-(4aα,6aα,11bα,13aR*,13bα)]-;13H-Benzo[a]furo[2,3,4-mn]xanthen-11-ol,1,2,3,4,4a,5,6,6a,11b,13b-decahydro-4,4,6a,9-tetramethyl-,(4aS,6aS,11bR,13aS,13bS)-;(4aS,6aS,11bR,13aS,13bS)-2,3,4,4a,5,6,6a,13b-Octahydro-4,4,6a,9-tetramethyl-1H,11bH,13H-benzo[a]furo[2,3,4-mn]xanthen-11-ol;1,2,3,4,4a,5,6,6a,11b,13b-Decahydro-4,4,6a,9-tetramethyl-13H-benzo[a]furo[2,3,4-mn]xanthen-11-ol;Tackle;NSC 135048;(-)-Siccanin
Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs

Description

Siccanin is an organic heteropentacyclic compound. It has a role as an antifungal drug and a fungal metabolite.|Siccanin is a succinate dehydrogenase inhibitor originally isolated from the pathogenic fungus Helminthosposium siccans with antifungal activity. Siccanin, in a quinone-dependent manner, inhibits succinate dehydrogenase in the terminal electron transport chain thereby disrupting cellular respiration.

(-)-Siccanin Basic Attributes

Molecular Weight：

342.476

Exact Mass：

342.47

UNII：

L702S858Z6

DSSTox ID：

DTXSID1046843

NCI Thesaurus Code：

C75207

Characteristics

PSA：

38.69000

XLogP3：

5.14570

Density：

1.18g/cm3

Melting Point：

139-140 °C

Boiling Point：

427.8ºC at 760mmHg

Flash Point：

212.5ºC

Refractive Index：

1.593

Toxicity：

LD50 in mice, rats (mg/kg): >6000, >1000 orally; >3000, >600 s.c. or i.p. (Suzuki)

Specific rotation：

D20 -136° (c = 2 in chloroform)

Drug Information

MeSH Entry Terms：

siccanin

(-)-Siccanin Use and Manufacturing

Siccanin is an unusual, fused, phenolic pentacycle first isolated from Helminthosporium siccans and reported in 1962 as a potent antifungal agent. Siccanin inhibits succinate dehydrogenase in the terminal electron transport system. More recent studies note the proximity of the siccanin binding site to the quinone-binding site of the enzyme. Species-selective inhibition by siccanin is unique among succinate dehydrogenase inhibitors and offers a lead for new chemotherapeutics.

Computed Properties

Molecular Weight:342.5
XLogP3:4.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:342.21949481
Monoisotopic Mass:342.21949481
Topological Polar Surface Area:38.7
Heavy Atom Count:25
Complexity:560
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes