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Herboxidiene

CAT: 0804-HY-19828-02Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-19828-02Size:1 mg
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Description
Herboxidiene (GEX1A) is a potent phytotoxic polyketide from Streptomyces sp. A7847 with a diverse range of activities, including herbicidal, anti-cholesterol, anti-tumor effects. Herboxidiene inhibits the pre-mRNA splicing process by binding to spliceosome-associated protein (SAP) 155, a subunit of SF3b, in the splicesome[1][2].
CAS Number
142861-00-5
Product Name Alternative
GEX1A
UNSPSC
12352005
Hazard Statement
H315, H319, H335
Target
DNA/RNA Synthesis
Type
Natural Products
Related Pathways
Cell Cycle/DNA Damage
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/herboxidiene.html
Purity
99.02
Solubility
DMSO : 4 mg/mL (ultrasonic; warming)
Smiles
C[C@H]([C@H]([C@H](O)C)OC)[C@@]1([H])O[C@]1(C)C[C@@H](/C=C/C=C(C)/[C@H]2O[C@@H](CC(O)=O)CC[C@@H]2C)C
Molecular Formula
C25H42O6
Molecular Weight
438.60
Precautions
H315, H319, H335
References & Citations
[1]Pokhrel AR, et al. Herboxidiene biosynthesis, production, and structural modifications: prospect for hybrids with related polyketide. Appl Microbiol Biotechnol. 2015;99 (20) :8351‐8362.|[2]Sakai Y, et al. GEX1 compounds, novel antitumor antibiotics related to herboxidiene, produced by Streptomyces sp. I. Taxonomy, production, isolation, physicochemical properties and biological activities. J Antibiot (Tokyo) . 2002;55 (10) :855‐862.|[3]Miller-Wideman M, et al. Herboxidiene, a new herbicidal substance from Streptomyces chromofuscus A7847. Taxonomy, fermentation, isolation, physico-chemical and biological properties. J Antibiot (Tokyo) . 1992;45 (6) :914‐921.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C (Powder, protect from light, stored under nitrogen)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Herboxidiene

herboxidiene has been reported in Streptomyces chromofuscus with data available.

CAS Number142861-00-5
PubChem CID6438496
IUPAC Name2-[(2R,5S,6S)-6-[(2E,4E,6S)-7-[(2R,3R)-3-[(2R,3R,4R)-4-hydroxy-3-methoxypentan-2-yl]-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl]-5-methyloxan-2-yl]acetic acid
Molecular FormulaC25H42O6
Molecular Weight438.6
XLogP4.1
Topological Polar Surface Area88.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count11
Heavy Atom Count31
Formal Charge0
Complexity658
SMILES
C[C@H]1CC[C@@H](O[C@@H]1/C(=C/C=C/[C@@H](C)C[C@@]2([C@H](O2)[C@H](C)[C@H]([C@@H](C)O)OC)C)/C)CC(=O)O
InChI
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
InChIKey
ISZXEMUWHQLLTC-LSIVYLFASA-N
Chemical Structure
2D Structure
2D structure of Herboxidiene
CAS: 142861-00-5
CID: 6438496
Formula: C25H42O6
MW: 438.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight438.6
XLogP34.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count11
Exact Mass438.29813906
Monoisotopic Mass438.29813906
Topological Polar Surface Area88.5 Ų
Heavy Atom Count31
Formal Charge0
Complexity658
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
ENZ-CHM487-0005Herboxidiene

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