Hederagenin - analytical standard, ≥98% , CAS No.465-99-6

CAS: 465-99-6 Cat. No.: H110221 Molecular Weight: 472.7 EC Number: 207-369-9

GRADE & PURITY Analytical standard, ≥98%

Synonyms

Olean-12-en-28-oic acid, 3.beta.,23-dihydroxy- | AKOS016036289 | BDBM50442880 | CCG-269472 | (3-beta,4-alpha)-3,23-Dihydroxyolean-12-en-28-oic acid | (4AS,6AS,6BR,8AR,9R,10S,12AR,12BR,14BS)-10-HYDROXY-9-(HYDROXYMETHYL)-2,2,6A,6B,9,12A-HEXAMETHYL-1,2,3,4,4

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Hederagenin (3,23-Dihydroxyolean-12-en-28-acid), a triterpenoid saponin, is used to study the properties of triterpenoid saponins as biopesticides that prevent fungal growth, bacterial growth, and viral plant diseases. Hederagenin may be used as a reference in assays to detect it in biological fluids.

Specifications

Synonyms

Olean-12-en-28-oic acid, 3.beta., 23-dihydroxy- | AKOS016036289 | BDBM50442880 | CCG-269472 | (3-beta, 4-alpha)-3, 23-Dihydroxyolean-12-en-28-oic acid | (4AS, 6AS, 6BR, 8AR, 9R, 10S, 12AR, 12BR, 14BS)-10-HYDROXY-9-(HYDROXYMETHYL)-2, 2, 6A, 6B, 9, 12A-HEXAMETHYL-1, 2, 3, 4, 4

Specifications & Purity

analytical standard, ≥98%

Biochemical and Physiological Mechanisms

Saponin. Anti-inflammatory.

Storage

Store at 2-8°C

Shipped In

Wet ice

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

Grade

Analytical standard

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)O)C)C)C2C1)C)C(=O)O)C
• IUPAC Name: (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• InChIKey: PGOYMURMZNDHNS-MYPRUECHSA-N
• INCHI: 1S/C30H48O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)/t20-,21+,22+,23-,26-,27-,28+,29+,30-/m0/s1
• Isomeric SMILES: C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)CO)O
• WGK Germany: 3
• Molecular Weight: 472.7
• Reaxy-Rn: 2026440
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2026440&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: Triterpenoids
• Alternative Parents: Steroids and steroid derivatives Secondary alcohols Cyclic alcohols and derivatives Monocarboxylic acids and derivatives Carboxylic acids Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Triterpenoid - Steroid - Cyclic alcohol - Secondary alcohol - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Carbonyl group - Alcohol - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
• External Descriptors: dihydroxy monocarboxylic acid - pentacyclic triterpenoid - sapogenin

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)

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2 Activities)

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F3 Tclin Tissue factor (1 Activities)

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EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

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ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)

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NQO1 Tchem Quinone reductase 1 (1746 Activities)

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A-375 (9258 Activities)

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AGS (1999 Activities)

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BGC-823 (3035 Activities)

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DLD-1 (17511 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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M14 (47487 Activities)

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MCF7 (126967 Activities)

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NCI-H1975 (4994 Activities)

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MKN-45 (2102 Activities)

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SW-1736 (356 Activities)

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A549 (127892 Activities)

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FaDu (1726 Activities)

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HepG2 (196354 Activities)

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A2780 (11979 Activities)

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KB (17409 Activities)

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HeLa (62764 Activities)

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MDA-MB-231 (73002 Activities)

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8505C (583 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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PRKAA2 Tchem AMP-activated protein kinase, AMPK (12273 Activities)

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USP7 Tchem Ubiquitin carboxyl-terminal hydrolase 7 (837 Activities)

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NCI-H187 (598 Activities)

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L02 (4864 Activities)

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Associated Targets(non-human)

Coagulation factor III (5 Activities)

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Abcb1b P-glycoprotein 1 (174 Activities)

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Leishmania infantum (5912 Activities)

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Carassius auratus (65 Activities)

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Hepatitis C virus (23859 Activities)

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NIH3T3 (5395 Activities)

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Oreochromis (28 Activities)

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Pomacea canaliculata (20 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 472.700 g/mol
• XLogP3: 6.800
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 472.355 Da
• Monoisotopic Mass: 472.355 Da
• Topological Polar Surface Area: 77.800 Ų
• Heavy Atom Count: 34
• Formal Charge: 0
• Complexity: 907.000
• 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. Li Pengfei, Peng Jun, Li Yuexin, Gong Lili, Lv Yali, Liu He, Zhang Tianhong, Yang Song, Liu Hongchuan, Li Jinglai, Liu Lihong.  (2021)  Pharmacokinetics, Bioavailability, Excretion and Metabolism Studies of Akebia Saponin D in Rats: Causes of the Ultra-Low Oral Bioavailability and Metabolic Pathway.  Frontiers in Pharmacology,      [PMID:33935711] [10.3389/fphar.2021.621003]

2. Junyan Wang, Minmin Huang, Haihong Hu, Lushan Yu, Su Zeng.  (2014)  Pregnane X receptor-mediated transcriptional activation of UDP-glucuronosyltransferase 1A1 by natural constituents from foods and herbs.  FOOD CHEMISTRY,      [PMID:24996308] [10.1016/j.foodchem.2014.05.004]

3. Huan Liu, Liying Liang, Minggang Wang, Qinfeng Huang, Yu Pan, Xiaojie Wei, Wenchao Zhang.  (2026)  Establishment of a Novel Monoclonal Antibody Based icELISA Method to Determine the Total Content of Ursolic and Oleanolic Acids in Fruits.  JOURNAL OF FOOD COMPOSITION AND ANALYSIS,      [PMID:] [10.1016/j.jfca.2026.109072]