N-[(2S,3S,4S,6R)-6-[[(1S,3R,6S,7E,9S,11E,13S,16S,17S,18S,20S,21R,22S,23E)-17-[(2S,4R,5R,6R)-5-[(2R,4R,5S,6R)-5-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-[(2S,5R,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-3-ethyl-23-hydroxy-8,10,12,18,20,22-hexamethyl-25,27-dioxo-26-oxapentacyclo[22.2.1.01,6.013,22.016,21]heptacosa-4,7,11,14,23-pentaen-9-yl]oxy]-4-hydroxy-2,4-dimethyloxan-3-yl]acetamide
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Grundinformationen
- CAS
158475-32-2- Standard-SMILES
CC[C@H]1C=C[C@H]2/C=C(\C)[C@@H](O[C@H]3C[C@](C)(O)[C@@H](NC(C)=O)[C@H](C)O3)C(C)/C=C(\C)[C@@H]3C=C[C@@H]4[C@@H](O[C@@H]5C[C@@H](O[C@H]6CC[C@@H](O)[C@H](C)O6)[C@H](O[C@@H]6C[C@@H](O)[C@H](O[C@@H]7C[C@@H](O)[C@H](O)[C@@H](C)O7)[C@@H](C)O6)[C@@H](C)O5)[C@@H](C)C[C@H](C)[C@H]4[C@]3(C)/C(O)=C3/C(=O)O[C@]2(C1)C3=O- InChIKey
QQZJNABARVXBJD-IXCNRNCNSA-N- Summenformel
Überblick
QQZJNABARVXBJD-IXCNRNCNSA-N has been reported in Lechevalieria aerocolonigenes with data available.
Namen und Bezeichner
- Bevorzugter Name
- N-[(2S,3S,4S,6R)-6-[[(1S,3R,6S,7E,9S,11E,13S,16S,17S,18S,20S,21R,22S,23E)-17-[(2S,4R,5R,6R)-5-[(2R,4R,5S,6R)-5-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-[(2S,5R,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-3-ethyl-23-hydroxy-8,10,12,18,20,22-hexamethyl-25,27-dioxo-26-oxapentacyclo[22.2.1.01,6.013,22.016,21]heptacosa-4,7,11,14,23-pentaen-9-yl]oxy]-4-hydroxy-2,4-dimethyloxan-3-yl]acetamide
- IUPAC
- N-[(2S,3S,4S,6R)-6-[[(1S,3R,6S,7E,9S,11E,13S,16S,17S,18S,20S,21R,22S,23E)-17-[(2S,4R,5R,6R)-5-[(2R,4R,5S,6R)-5-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-[(2S,5R,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-3-ethyl-23-hydroxy-8,10,12,18,20,22-hexamethyl-25,27-dioxo-26-oxapentacyclo[22.2.1.01,6.013,22.016,21]heptacosa-4,7,11,14,23-pentaen-9-yl]oxy]-4-hydroxy-2,4-dimethyloxan-3-yl]acetamide
- Englischer Name
- Saccharocarcin A
- Summenformel
- C67H101NO20
- Molmasse
- 1240.51354
Namen und Synonyme
Saccharocarcin A18H-16a,19-Metheno-16aH-benzo[b]naphth[2,1-j]oxacyclotetradecin-18,20(1H)-dione, 10-[[4-(acetylamino)-2,4,6-trideoxy-3-C-methylhexopyranosyl]oxy]-4-[[O-2,6-dideoxyhexopyranosyl-(1→4)-O-2,6-dideoxy-3-O-(tetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)hexopyranosyl-(1→4)-2,6-dideoxyhexopyranosyl]oxy]-15-e...
Datenbank-Bezeichner
- CAS
158475-32-2- PubChem CID
- 117072693
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 6,1
- Polarare Oberfläche (TPSA)
- 286 Ų
- H-Brücken-Donoren
- 7
- H-Brücken-Akzeptoren
- 20
- Frei drehbare Bindungen
- 12
- Schwere Atome
- 88
- Formalladung
- 0
- Komplexität
- 2.700
Physikochemische Eigenschaften
- Dichte
- 1.3 · 1.30±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- Löslichkeit
- DMF: Soluble; DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble
- Aggregatzustand
- A solid
- pka
- 4.5 · 4.50±1.00(Predicted)
Chemie und Industrie
Anwendungen
BeschreibungSaccharocarcin A is an antibiotic originally isolated from S. aerocolonigenes subsp. antibiotica. It is active against M. luteus, S. aureus, E. coli, P. aeruginosa, and C. albicans in a disc assay. Saccharocarcin A inhibits C. trachomatis infection by 88% without inducing cytotoxicity in McCoy cells when used at a concentration of 0.5 μg/ml.
VerwendenSaccharocarcin A is an unusual tetronic acid structurally related to kijanimicin, chlorothricin, tetrocarcin and versipelostatin, which has pronounced activity against Gram positive bacteria and Chlamydia trachomatis. Limited availability has restricted further investigation of this metabolite, however several members of this class have received considerable literature focus. Versipelostatin inhibits transcription from the promoter of GRP78, a gene that is activated as part of a stress signalling pathway under glucose deprivation resulting in unfolded protein response (UPR), causing death of glucose-deprived cells. Tetrocarcin A appears to target the phosphatidylinositide-3'-kinase/Akt signalling pathway.
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