Ailanthone - ≥98%(HPLC) , CAS No.981-15-7

CAS: 981-15-7 Cat. No.: A286967 Molecular Weight: 376.40 EC Number: 683-145-8

GRADE & PURITY ≥98%(HPLC)

Synonyms

o13-Dehydrochaparrinoneo13-Dehydrochaparrinone | 2H-1,11c-(Epoxymethano)phenanthro(10,1-bc)pyran-5,10(3H,6ah)-dione, 1,3a,4,7,7a,11,11a,11b-octahydro-8,11a-beta-dimethyl-3-methylene-1-alpha,2-beta,11-beta-trihydroxy- | Ailanthone, >=98% (HPLC) | HY-N1943

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

o13-Dehydrochaparrinoneo13-Dehydrochaparrinone | 2H-1, 11c-(Epoxymethano)phenanthro(10, 1-bc)pyran-5, 10(3H, 6ah)-dione, 1, 3a, 4, 7, 7a, 11, 11a, 11b-octahydro-8, 11a-beta-dimethyl-3-methylene-1-alpha, 2-beta, 11-beta-trihydroxy- | Ailanthone, >=98% (HPLC) | HY-N1943

Specifications & Purity

≥98%(HPLC)

Biochemical and Physiological Mechanisms

Potent androgen receptor (AR) inhibitor (IC50= 69 nM). Disrupts the AR-chaperone complex by binding p23 and blocking AR interaction with HSP90 causing UPS degradation of AR. Inhibits Huh7 cancer cell growth via G0/G1cell cycle arrest and apoptosisin vitro

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Purity

≥98%(HPLC)

Names and Identifiers

• Canonical Smiles: CC1=CC(=O)C(C2(C1CC3C45C2C(C(C(=C)C4CC(=O)O3)O)(OC5)O)C)O
• IUPAC Name: (1S,4R,5R,7S,11R,13S,17S,18S,19R)-4,5,17-trihydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-ene-9,16-dione
• InChIKey: WBBVXGHSWZIJST-RLQYZCPESA-N
• INCHI: 1S/C20H24O7/c1-8-4-12(21)16(24)18(3)10(8)5-13-19-7-26-20(25,17(18)19)15(23)9(2)11(19)6-14(22)27-13/h4,10-11,13,15-17,23-25H,2,5-7H2,1,3H3/t10-,11-,13+,15+,16+,17+,18+,19+,20-/m0/s1
• Isomeric SMILES: CC1=CC(=O)[C@H]([C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@]([C@@H](C(=C)[C@@H]4CC(=O)O3)O)(OC5)O)C)O
• RTECS: KT0930000
• Molecular Weight: 376.40
• Reaxy-Rn: 1441126
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1441126&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene lactones
• Intermediate Tree Nodes: Not available
• Direct Parent: Quassinoids
• Alternative Parents: Triterpenoids Naphthopyrans Naphthalenes Oxepanes Cyclohexenones Delta valerolactones Pyrans Oxanes Tetrahydrofurans Secondary alcohols Carboxylic acid esters Cyclic alcohols and derivatives Hemiacetals Polyols Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Triterpenoid - Polycyclic triterpenoid - C-20 quassinoid skeleton - Quassinoid - Naphthopyran - Naphthalene - Delta valerolactone - Delta_valerolactone - Oxepane - Cyclohexenone - Pyran - Oxane - Tetrahydrofuran - Cyclic alcohol - Secondary alcohol - Cyclic ketone - Carboxylic acid ester - Hemiacetal - Ketone - Lactone - Organoheterocyclic compound - Oxacycle - Carboxylic acid derivative - Polyol - Monocarboxylic acid or derivatives - Alcohol - Carbonyl group - Organooxygen compound - Organic oxide - Organic oxygen compound - Hydrocarbon derivative - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.
• External Descriptors: Dammarenes

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)

H9 (1832 Activities)

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

Associated Targets(non-human)

Entamoeba histolytica (2676 Activities)

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Plasmodium falciparum (966862 Activities)

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RAW264.7 (28094 Activities)

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 37.64, Max Conc. mM: 100
• Molecular Weight: 376.400 g/mol
• XLogP3: -1.100
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 376.152 Da
• Monoisotopic Mass: 376.152 Da
• Topological Polar Surface Area: 113.000 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 817.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• 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. Yue Zhang, Taiding Wu, Chang Li, Nianfang Luo, Jun Wang, Jingxian Li, Min Tian, Lei Liu, Ruiting Li, Jingyi Zhang.  (2025)  Ailanthone induces apoptosis in U-2OS cells through the endoplasmic reticulum stress.  Frontiers in Immunology,      [PMID:41112300] [10.3389/fimmu.2025.1633643]