Obacunone - 10mM in DMSO , CAS No.751-03-1

CAS: 751-03-1 Cat. No.: O425830 Molecular Weight: 454.51

GRADE & PURITY 10mM in DMSO

Synonyms

MLS002473187 | OBACUNON | Z3234884793 | Oxireno(4,4a)-2-benzopyrano(6,5-g)(2)benzoxepin-3,5,9(3aH,4bH,6H)-trione, 1-(3-furanyl)-1,6a,7,11a,11b,12,13,13a-octahydro-4b,7,7,11a,13a-pentamethyl-, (1S,3aS,4aR,4bR,6aR,11aR,11bR,11bR,13aS)- | CCG-269280 | EX-A48

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Obacunone has cytotoxicity in androgen-dependent human prostate Y cells. Obacunone exerts an antivirulence effect on S. Typhimurium and may serve as a lead compound for development of antivirulence strategies for S. Typhimurium. Obacunone may have the potential to prevent estrogen-responsive breast Y through inhibition of the aromatase enzyme and inflammatory pathways, as well as activation of apoptosis.

Specifications

Synonyms

MLS002473187 | OBACUNON | Z3234884793 | Oxireno(4, 4a)-2-benzopyrano(6, 5-g)(2)benzoxepin-3, 5, 9(3aH, 4bH, 6H)-trione, 1-(3-furanyl)-1, 6a, 7, 11a, 11b, 12, 13, 13a-octahydro-4b, 7, 7, 11a, 13a-pentamethyl-, (1S, 3aS, 4aR, 4bR, 6aR, 11aR, 11bR, 11bR, 13aS)- | CCG-269280 | EX-A48

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: CC1(C2CC(=O)C3(C(C2(C=CC(=O)O1)C)CCC4(C35C(O5)C(=O)OC4C6=COC=C6)C)C)C
• IUPAC Name: (1R,2R,4S,7S,8S,11R,12R,18R)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.02,4.02,8.012,18]icos-13-ene-5,15,20-trione
• InChIKey: MAYJEFRPIKEYBL-OASIGRBWSA-N
• INCHI: 1S/C26H30O7/c1-22(2)16-12-17(27)25(5)15(23(16,3)9-7-18(28)32-22)6-10-24(4)19(14-8-11-30-13-14)31-21(29)20-26(24,25)33-20/h7-9,11,13,15-16,19-20H,6,10,12H2,1-5H3/t15-,16+,19+,20-,23-,24+,25+,26-/m1/s1
• Isomeric SMILES: C[C@@]12CC[C@@H]3[C@]4(C=CC(=O)OC([C@@H]4CC(=O)[C@]3([C@@]15[C@H](O5)C(=O)O[C@H]2C6=COC=C6)C)(C)C)C
• Molecular Weight: 454.51
• Reaxy-Rn: 1360012
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1360012&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Triterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Triterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Limonoids
• Alternative Parents: Naphthopyrans Naphthalenes 1,4-dioxepanes Delta valerolactones Pyrans Oxanes Dicarboxylic acids and derivatives Heteroaromatic compounds Furans Enoate esters Ketones Oxacyclic compounds Epoxides Dialkyl ethers Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Limonoid skeleton - Naphthopyran - Naphthalene - 1,4-dioxepane - Delta valerolactone - Dioxepane - Delta_valerolactone - Dicarboxylic acid or derivatives - Pyran - Oxane - Heteroaromatic compound - Furan - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Lactone - Ketone - Carboxylic acid ester - Oxacycle - Ether - Oxirane - Dialkyl ether - Organoheterocyclic compound - Carboxylic acid derivative - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.
• External Descriptors: Limonoids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

MCF7 (126967 Activities)

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SW480 (6023 Activities)

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MDA-MB-435 (38290 Activities)

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MGLL Tchem Monoglyceride lipase (1909 Activities)

Discover Target: MGLL

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Spodoptera frugiperda (784 Activities)

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TGR Thioredoxin glutathione reductase (28579 Activities)

Discover Target: TGR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 454.500 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 454.199 Da
• Monoisotopic Mass: 454.199 Da
• Topological Polar Surface Area: 95.300 Ų
• Heavy Atom Count: 33
• Formal Charge: 0
• Complexity: 985.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Shaoqin Cen, Zhenxing Hou, Yuan Zhang, Nan Wang, Zihe Zhao, Ao Li, Guoqiang Wan, Tianhong Zhang, Xia Gao.  (2026)  Obacunone mitigates cisplatin-induced ototoxicity by activating CRHBP-mediated autophagy.  BIOCHEMICAL PHARMACOLOGY,      [PMID:41611132] [10.1016/j.bcp.2026.117759]