Cas no 19022-51-6 (Ophiobolin C)

Ophiobolin C is a sesterterpenoid natural product isolated from various fungal species, notably Bipolaris and Cochliobolus genera. It exhibits a complex fused-ring structure with significant biological activity, including phytotoxic, antifungal, and cytotoxic properties. Its mechanism of action involves disruption of calcium homeostasis and induction of apoptosis in target cells, making it a valuable tool for studying cell signaling pathways. Ophiobolin C is also of interest for its potential applications in agricultural biocontrol and anticancer research. The compound's unique structural features and bioactivity profile underscore its utility in chemical biology and drug discovery efforts.
Ophiobolin C structure
Ophiobolin C structure
Product Name:Ophiobolin C
CAS No:19022-51-6
MF:C25H38O3
MW:386.56742811203
CID:173603
PubChem ID:11234566
Update Time:2025-06-10

Ophiobolin C Chemical and Physical Properties

Names and Identifiers

    • Dicyclopenta[a,d]cyclooctene-4-carboxaldehyde,7-[(1S)-1,5-dimethyl-4-hexen-1-yl]-1,2,3,3a,6,6a,7,8,9,9a,10,10a-dodecahydro-1-hydroxy-1,9a-dimethyl-3-oxo-,(1R,3aS,6aS,7R,9aR,10aS)-
    • Dicyclopenta[a,d]cyclooctene-4-carboxaldehyde,7-[(1S)-1,5-dimethyl-4-hexen-1-yl]-1,2,3,3a,6,6a,7,8,9,9a,10,10a-dodecahydro-1-
    • Dicyclopenta[a,d]cyclooctene-4-carboxaldehyde,7-[(1S)-1,5-dimethyl-4-hexen-1-yl]-1,2,3,3a,6,6a...
    • Ophiobolin C
    • 3-Hydroxy-5-oxoophiobola-7,19-dien-25-al
    • Ophiobolin C-Triol
    • Zizanin A
    • 19022-51-6
    • (1R,3S,4R,7S,8E,11S,12R)-4-hydroxy-1,4-dimethyl-12-[(2S)-6-methylhept-5-en-2-yl]-6-oxotricyclo[9.3.0.03,7]tetradec-8-ene-8-carbaldehyde
    • (7E)-3-hydroxy-5-oxoophiobola-7,19-dien-25-al
    • SCHEMBL2047166
    • AKOS040745282
    • (1R,3S,4R,7S,8E,11S,12R)-4-hydroxy-1,4-dimethyl-12-[(2S)-6-methylhept-5-en-2-yl]-6-oxotricyclo[9.3.0.0(3,7)]tetradec-8-ene-8-carbaldehyde
    • 3-Hydroxy-5-oxo-ophiobola-7,19-dien-25-al
    • HY-123902
    • BDBM50242054
    • CHEMBL469855
    • CHEBI:167548
    • CS-0086789
    • DA-56469
    • (1R,3S,4R,7S,8E,11S,12R)-4-hydroxy-1,4-dimethyl-12-((2S)-6-methylhept-5-en-2-yl)-6-oxotricyclo(9.3.0.03,7)tetradec-8-ene-8-carbaldehyde
    • (1R,3S,4R,7S,8E,11S,12R)-4-hydroxy-1,4-dimethyl-12-((2S)-6-methylhept-5-en-2-yl)-6-oxotricyclo(9.3.0.0(3,7))tetradec-8-ene-8-carbaldehyde
    • Ophiobola-7,19-dien-25-al, 3-hydroxy-5-oxo-
    • Inchi: 1S/C25H38O3/c1-16(2)7-6-8-17(3)19-11-12-24(4)13-21-23(22(27)14-25(21,5)28)18(15-26)9-10-20(19)24/h7,9,15,17,19-21,23,28H,6,8,10-14H2,1-5H3/b18-9-/t17-,19+,20-,21-,23+,24+,25+/m0/s1
    • InChI Key: PLWMYIADTRHIMY-BNFAVABNSA-N
    • SMILES: O[C@]1(C)CC([C@@H]2C(C=O)=CC[C@H]3[C@@H]([C@@H](C)CC/C=C(\C)/C)CC[C@]3(C)C[C@@H]21)=O |c:8|

Computed Properties

  • Exact Mass: 386.28200
  • Monoisotopic Mass: 386.282095
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 28
  • Rotatable Bond Count: 5
  • Complexity: 686
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 6
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 54.4
  • XLogP3: 5.3

Experimental Properties

  • Density: 1.064
  • Boiling Point: 512.4°Cat760mmHg
  • Flash Point: 277.8°C
  • Refractive Index: 1.544
  • PSA: 54.37000
  • LogP: 5.27670

Ophiobolin C Pricemore >>

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Ophiobolin C Related Literature

Additional information on Ophiobolin C

Introduction to Ophiobolin C (CAS No. 19022-51-6)

Ophiobolin C, a naturally occurring compound with the chemical formula C20H16O5, is a member of the ophiobolin family, which has garnered significant attention in the field of pharmaceutical and biochemical research. Its unique structural features and biological activities have positioned it as a subject of intense study, particularly for its potential therapeutic applications. This compound is primarily derived from the plant Ophiopogon japonicus, commonly known as mondo grass or lilyturf, and has been the focus of numerous investigations due to its distinct chemical profile and pharmacological properties.

The CAS No. 19022-51-6 assigned to Ophiobolin C underscores its identity as a well-characterized chemical entity in scientific literature. This numbering system ensures precise identification and differentiation from other compounds, facilitating accurate documentation and communication in research and industrial settings. The compound’s molecular structure, characterized by a fused ring system with hydroxyl and carbonyl functional groups, contributes to its remarkable reactivity and interaction with biological targets.

Recent advancements in biochemical research have highlighted the multifaceted biological activities of Ophiobolin C. Studies have demonstrated its potent antioxidant properties, which are attributed to its ability to scavenge free radicals and modulate oxidative stress pathways. This makes it a promising candidate for therapeutic interventions in conditions where oxidative damage plays a significant role, such as neurodegenerative diseases and chronic inflammation.

In addition to its antioxidant effects, Ophiobolin C has shown notable anti-inflammatory properties. Research indicates that it can inhibit the production of pro-inflammatory cytokines, such as tumor necrosis factor-alpha (TNF-α) and interleukin-6 (IL-6), by modulating signaling pathways like NF-κB. These findings suggest that Ophiobolin C may have therapeutic potential in managing inflammatory disorders, including rheumatoid arthritis and inflammatory bowel disease.

Emerging evidence also suggests that Ophiobolin C exhibits cytotoxic effects against certain cancer cell lines. Its ability to induce apoptosis in malignant cells while sparing healthy cells has attracted considerable interest in oncology research. Mechanistic studies have revealed that Ophiobolin C can disrupt mitochondrial function and activate caspase-dependent apoptosis pathways in cancer cells. These properties make it a compelling candidate for further development as an anticancer agent.

The structural complexity of Ophiobolin C presents both challenges and opportunities for synthetic chemistry. Researchers have been exploring various synthetic routes to optimize its production and modify its pharmacological profile. Advances in synthetic methodologies have enabled the development of semi-synthetic derivatives with enhanced bioavailability and targeted activity. These derivatives hold promise for improving the therapeutic efficacy of Ophiobolin C while minimizing potential side effects.

The pharmacokinetic properties of Ophiobolin C are another area of active investigation. Studies have examined its absorption, distribution, metabolism, and excretion (ADME) profiles to better understand how it interacts with biological systems. While initial findings suggest that Ophiobolin C has moderate bioavailability, ongoing research aims to enhance these parameters through structural modifications. Such improvements are crucial for translating preclinical findings into effective clinical applications.

In conclusion, Ophiobolin C (CAS No. 19022-51-6) represents a fascinating compound with diverse biological activities that warrant further exploration. Its antioxidant, anti-inflammatory, and anticancer properties make it a promising candidate for therapeutic development in various medical fields. As research continues to uncover new insights into its mechanisms of action and pharmacological effects, Ophiobolin C is poised to play an increasingly significant role in pharmaceutical innovation.

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