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C2389

Sigma-Aldrich

Cerulenin

from Cephalosporium caerulens, ≥98% (HPLC), powder, de novo phospholipid synthesis inhibitor

Synonyme(s) :

Helicocerin, (2R,3S,E,E)-2,3-Epoxy-4-oxo-7,10-dodecadienamide

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About This Item

Formule empirique (notation de Hill):
C12H17NO3
Numéro CAS:
17397-89-6
Poids moléculaire :
223.27
Numéro Beilstein :
4140423
Numéro CE :
241-424-8
Numéro MDL:
MFCD00083595
Code UNSPSC :
51111800
ID de substance PubChem :
24892323
Nomenclature NACRES :
NA.77

product name

Cerulenin, ≥98% (HPLC), from Cephalosporium caerulens

Source biologique

Cephalosporium caerulens

Niveau de qualité

200

Pureté

≥98% (HPLC)

Forme

powder

Pf

93 °C

Solubilité

acetone: 19.60-20.40 mg/mL, clear to slightly hazy, colorless to yellow

Spectre d'activité de l'antibiotique

fungi

Mode d’action

enzyme | inhibits

Température de stockage

−20°C

Chaîne SMILES 

C/C=C/C/C=C/CCC([C@@H]1[C@H](C(N)=O)O1)=O

InChI

1S/C13H18O3/c1-3-4-5-6-7-8-9-11(15)13-12(16-13)10(2)14/h3-4,6-7,12-13H,5,8-9H2,1-2H3/b4-3+,7-6+/t12-,13+/m0/s1

Clé InChI

PTNNGEBMCNMENY-JIVMHGEESA-N

Informations sur le gène

human ... FASN(2194)

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Description générale

Cerulenin, an inhibitor of de novo phospholipid synthesis triggers apoptosis in various wild type p53 and mutant p53 tumor cell lines. This fungal antibiotic also blocks the condensing enzyme involved in fatty acid and polyketide biosynthesis.

Application

Cerulenin has been used:

  • as a fatty acid synthase inhibitor to study its effects on aldosterone-induced trained immunity
  • as a blocker of fatty acid synthase to study its effects on the replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV2)
  • as a supplement in yeast extract–peptone–dextrose/glycerol (YPD/G) agar plates for the isolation of cerulenin-resistant yeast strains

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Sabrina Schubert et al.
Antimicrobial agents and chemotherapy, 55(5), 2212-2223 (2011-03-16)
Constitutive overexpression of the Mdr1 efflux pump is an important mechanism of acquired drug resistance in the yeast Candida albicans. The zinc cluster transcription factor Mrr1 is a central regulator of MDR1 expression, but other transcription factors have also been
Nepovirus
Sanfacon H, et al.
Encyclopedia of Virology (2008)
Jennifer W Lou et al.
Scientific reports, 9(1), 12987-12987 (2019-09-12)
During fatty acid biosynthesis, acyl carrier proteins (ACPs) from type I fungal fatty acid synthase (FAS) shuttle substrates and intermediates within a reaction chamber that hosts multiple spatially-fixed catalytic centers. A major challenge in understanding the mechanism of ACP-mediated substrate
Su Gao et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 301(1), R209-R217 (2011-04-22)
Hypothalamic fatty acid metabolism is involved in central nervous system controls of feeding and energy balance. Malonyl-CoA, an intermediate of fatty acid biosynthesis, is emerging as a significant player in these processes. Notably, hypothalamic malonyl-CoA has been implicated in leptin's
Darren C J Wong et al.
Frontiers in plant science, 9, 839-839 (2018-07-05)
Hundreds of orchid species secure pollination by sexually luring specific male insects as pollinators by chemical and morphological mimicry. Yet, the biochemical pathways involved in the synthesis of the insect sex pheromone-mimicking volatiles in these sexually deceptive plants remain poorly
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