Alantolactone - analytical standard, ≥97%(HPLC) , CAS No.546-43-0

CAS: 546-43-0 Cat. No.: A114070 Molecular Weight: 232.32 EC Number: 208-899-3

GRADE & PURITY Analytical standard, ≥97%(HPLC)

Synonyms

(3aR,5S,8aR,9aR)-5,8a-Dimethyl-3-methylene-3,3a,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(5H)-one | Q21099633 | DTXSID90877864 | KBio3_002395 | D-Catechin | Stanzamine | 2-Amino-4,5-methylenehex-5-enoic acid | NCGC00178225-01 | Spectrum4_001772 | NSC 9

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Alantolactone is a sesquiterpene lactone disrupts the Cripto-1/ActRII complexes, resulting in an induction of activin/SMAD3 signaling. Alantolactone inhibits proliferation in cancer cells with no affect on normal cells

Specifications

Synonyms

(3aR, 5S, 8aR, 9aR)-5, 8a-Dimethyl-3-methylene-3, 3a, 6, 7, 8, 8a, 9, 9a-octahydronaphtho[2, 3-b]furan-2(5H)-one | Q21099633 | DTXSID90877864 | KBio3_002395 | D-Catechin | Stanzamine | 2-Amino-4, 5-methylenehex-5-enoic acid | NCGC00178225-01 | Spectrum4_001772 | NSC 9

Specifications & Purity

analytical standard, ≥97%(HPLC)

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Analytical standard

Purity

≥97%(HPLC)

Names and Identifiers

• Canonical Smiles: CC1CCCC2(C1=CC3C(C2)OC(=O)C3=C)C
• IUPAC Name: (3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylidene-5,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one
• InChIKey: PXOYOCNNSUAQNS-AGNJHWRGSA-N
• INCHI: 1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h7,9,11,13H,2,4-6,8H2,1,3H3/t9-,11+,13+,15+/m0/s1
• Isomeric SMILES: C[C@H]1CCC[C@]2(C1=C[C@H]3[C@@H](C2)OC(=O)C3=C)C
• WGK Germany: 3
• Molecular Weight: 232.32
• Reaxy-Rn: 102198
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=102198&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Terpene lactones
        • Level5 Sesquiterpene lactones
          • Level6 Eudesmanolides, secoeudesmanolides, and derivatives

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene lactones
• Intermediate Tree Nodes: Sesquiterpene lactones
• Direct Parent: Eudesmanolides, secoeudesmanolides, and derivatives
• Alternative Parents: Sesquiterpenoids Naphthofurans Gamma butyrolactones Tetrahydrofurans Enoate esters Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Eudesmanolide - Sesquiterpenoid - Naphthofuran - Gamma butyrolactone - Tetrahydrofuran - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Lactone - Carboxylic acid ester - Oxacycle - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organoheterocyclic compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Carbonyl group - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.
• External Descriptors: Eudesmane sesquiterpenoids

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)

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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PARP1 Tclin Poly [ADP-ribose] polymerase-1 (6206 Activities)

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A498 (42825 Activities)

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ACHN (49357 Activities)

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CAKI-1 (44928 Activities)

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CCRF-CEM (65223 Activities)

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COLO 205 (50209 Activities)

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DU-145 (51482 Activities)

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HL-60 (67320 Activities)

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HT-1080 (3966 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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KM12 (47707 Activities)

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M14 (47487 Activities)

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MCF7 (126967 Activities)

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MOLT-4 (49676 Activities)

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OVCAR-3 (48710 Activities)

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OVCAR-4 (44535 Activities)

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OVCAR-5 (45555 Activities)

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OVCAR-8 (47708 Activities)

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PC-3 (62116 Activities)

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RPMI-8226 (44974 Activities)

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RXF 393 (41971 Activities)

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SF-295 (48000 Activities)

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SK-MEL-2 (46422 Activities)

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SK-MEL-28 (48833 Activities)

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SK-MEL-5 (47095 Activities)

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SK-OV-3 (52876 Activities)

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SN12C (47755 Activities)

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SNB-19 (46794 Activities)

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TK-10 (45540 Activities)

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U-251 (51189 Activities)

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UACC-257 (46019 Activities)

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UACC-62 (47335 Activities)

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UO-31 (46270 Activities)

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786-0 (47912 Activities)

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A549 (127892 Activities)

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NCI/ADR-RES (33767 Activities)

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T47D (39041 Activities)

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EKVX (44102 Activities)

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NCI-H322M (45589 Activities)

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HCC 2998 (41480 Activities)

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HCT-116 (91556 Activities)

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HOP-92 (41141 Activities)

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Hs-578T (29457 Activities)

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HepG2 (196354 Activities)

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NCI-H460 (60772 Activities)

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SF-268 (49410 Activities)

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HUVEC (11049 Activities)

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IGROV-1 (47897 Activities)

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Associated Targets(non-human)

murA UDP-N-acetylglucosamine 1-carboxyvinyltransferase (389 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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P388 (20296 Activities)

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RAW264.7 (28094 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Aedes atropalpus (23 Activities)

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MYB Transcriptional activator Myb (118 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: light sensitive
• Molecular Weight: 232.320 g/mol
• XLogP3: 3.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 232.146 Da
• Monoisotopic Mass: 232.146 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 421.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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. Zhang Yafei, Yang Bingqian, Tu Chengwei, Ping Yifan, Chen Shuhong, Wu Tong, Zhao Zheyu, Mao Yixin, Yang Zhan, Cao Zelin, Li Jianmin, Huang Kate, Ding Xi, Wu Gang, Zou Peng, Deng Zhennan, Sun Xiaoyu.  (2023)  Mitochondrial impairment and downregulation of Drp1 phosphorylation underlie the antiproliferative and proapoptotic effects of alantolactone on oral squamous cell carcinoma cells.  Journal of Translational Medicine,  21  (1): (1-17).  [PMID:37198593] [10.1186/s12967-023-04188-2]

2. Qiburi Qiburi, Tsogzolmaa Ganbold, Aoqier Aoqier, Dezhi Yang, Zhiyu Su, Mingming Bao, Meng He, Saren Gaowa, Temuqile Temuqile, Huricha Baigude.  (2022)  Analysis and identification of key anti-inflammatory molecules in Eerdun Wurile and exploration of their mechanism of action in microglia.  JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,      [PMID:36183605] [10.1016/j.jchromb.2022.123458]

3. Qiburi Qiburi, Temuqile Temuqile, Huricha Baigude.  (2021)  Synergistic Regulation of Microglia Gene Expression by Natural Molecules in Herbal Medicine.  Evidence-based Complementary and Alternative Medicine,      [PMID:34457033] [10.1155/2021/9920364]

4. Bao Shihui, Zheng Hailun, Ye Jinyao, Huang Huirong, Zhou Bin, Yao Qing, Lin Guangyong, Zhang Hailin, Kou Longfa, Chen Ruijie.  (2021)  Dual Targeting EGFR and STAT3 With Erlotinib and Alantolactone Co-Loaded PLGA Nanoparticles for Pancreatic Cancer Treatment.  Frontiers in Pharmacology,      [PMID:33815107] [10.3389/fphar.2021.625084]

5. Peihai Cao, Yiqun Xia, Wei He, Tingting Zhang, Lin Hong, Peisen Zheng, Xin Shen, Guang Liang, Ri Cui, Peng Zou.  (2019)  Enhancement of oxaliplatin-induced colon cancer cell apoptosis by alantolactone, a natural product inducer of ROS.  International Journal of Biological Sciences,      [PMID:31360110] [10.7150/ijbs.35265]

6. Yao Yao, Xia Dandan, Bian Yueping, Sun Yueyue, Zhu Feng, Pan Bin, Niu Mingshan, Zhao Kai, Wu Qingyun, Qiao Jianlin, Fu Chunling, Li Zhenyu, Xu Kailin.  (2015)  Alantolactone induces G1 phase arrest and apoptosis of multiple myeloma cells and overcomes bortezomib resistance.  APOPTOSIS,  20  (8): (1122-1133).  [PMID:26033479] [10.1007/s10495-015-1140-2]