A polyketide with diverse biological activities
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Herboxidiene

Item No. 25136

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,6-anhydro-6-C-[(2S,3E,5E)-6-[(2S,3S,6R)-6-(carboxymethyl)tetrahydro-3-methyl-2H-pyran-2-yl]-2-methyl-3,5-heptadien-1-yl]-1,4,7-trideoxy-4-methyl-3-O-methyl-L-glycero-L-gluco-heptitol
CAS Number
142861-00-5
Synonyms
  • GEX1A
  • Tan 1609
Molecular Formula
C25H42O6
Formula Weight
438.6
Purity
≥70%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Dichloromethane: solubleDMSO: solubleEthanol: solubleMethanol: solubleMethanol: Sparingly soluble: 1-10 mg/ml
SMILES
O=C(O)C[C@@H]1O[C@H](/C(C)=C/C=C/[C@@H](C)C[C@@]2(C)O[C@]2([H])[C@H](C)[C@@H](OC)[C@H](O)C)[C@@H](C)CC1
InChi Code
InChI=1S/C25H42O6/c1-15(14-25(6)24(31-25)18(4)23(29-7)19(5)26)9-8-10-16(2)22-17(3)11-12-20(30-22)13-21(27)28/h8-10,15,17-20,22-24,26H,11-14H2,1-7H3,(H,27,28)/b9-8+,16-10+/t15-,17+,18-,19-,20-,22-,23-,24-,25-/m1/s1
InChi Key
ISZXEMUWHQLLTC-LSIVYLFASA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Herboxidiene is a polyketide originally isolated from S. chromofuscus that has diverse biological activities.1,2,3,4,5 It inhibits growth of HeLa S3, SK-MEL-2, PC3, A549, and EBC-1 cells with GI50 values ranging from 7.4 to 62 nM.3 Herboxidiene is cytostatic against human umbilical vein endothelial cells (HUVECs; (IC50 = 26 nM)) and inhibits VEGF-induced invasion and tube formation of serum-starved HUVECs in a concentration-dependent manner, indicating antiangiogenic activity.4 Herboxidiene (0.05 μM) inhibits HIF-1α mRNA splicing and reduces HIF-1α protein levels in HepG2 cells grown under hypoxic conditions. It also inhibits splicing of p27Kip mRNA in HeLa cells in a concentration-dependent manner via interaction with the SAP155 subunit of the SF3b complex.2 Herboxidiene (0.1 and 1 μM) increases LDL receptor promoter-driven transcription in a cell-based reporter assay.5

    WARNING This product is not for human or veterinary use.