Helvolic acid - Moligand™, ≥96% , CAS No.29400-42-8

CAS: 29400-42-8 Cat. No.: H274834 Molecular Weight: 568.7

GRADE & PURITY Moligand™, ≥96%

Synonyms

(2Z)-2-[(4S,5S,6S,8S,9S,10R,13R,14S,16S)-6,16-Diacetyloxy-4,8,10,14-tetramethyl-3,7-dioxo-5,6,9,11,12,13,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoicacid

Storage

Protected from light,Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Store at -20°C. It is important to note that this product is reported to be light sensitive. Store In the Dark. Store under desiccating conditions.

Specifications

Synonyms

(2Z)-2-[(4S, 5S, 6S, 8S, 9S, 10R, 13R, 14S, 16S)-6, 16-Diacetyloxy-4, 8, 10, 14-tetramethyl-3, 7-dioxo-5, 6, 9, 11, 12, 13, 15, 16-octahydro-4H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoicacid

Specifications & Purity

Moligand™, ≥96%

Biochemical and Physiological Mechanisms

Mycotoxin. Broad spectrum antibiotic agent. Weakly inhibits GTPase. Active against Gram positive and negative bacteria. Inhibits protein biosynthesis via EF-2. Shows antioxidant effects.

Storage

Protected from light, Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥96%

Names and Identifiers

• Canonical Smiles: CC1C2C(C(=O)C3(C(C2(C=CC1=O)C)CCC4C3(CC(C4=C(CCC=C(C)C)C(=O)O)OC(=O)C)C)C)OC(=O)C
• IUPAC Name: (2Z)-2-[(4S,5S,6S,8S,9S,10R,13R,14S,16S)-6,16-diacetyloxy-4,8,10,14-tetramethyl-3,7-dioxo-5,6,9,11,12,13,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid
• InChIKey: MDFZYGLOIJNNRM-OAJDADRGSA-N
• INCHI: 1S/C33H44O8/c1-17(2)10-9-11-21(30(38)39)26-22-12-13-25-31(6)15-14-23(36)18(3)27(31)28(41-20(5)35)29(37)33(25,8)32(22,7)16-24(26)40-19(4)34/h10,14-15,18,22,24-25,27-28H,9,11-13,16H2,1-8H3,(H,38,39)/b26-21-/t18-,22+,24+,25+,27-,28+,31-,32+,33-/m1/s1
• Isomeric SMILES: C[C@H]1[C@@H]2[C@@H](C(=O)[C@]3([C@H]([C@]2(C=CC1=O)C)CC[C@@H]\4[C@@]3(C[C@@H](/C4=C(/CCC=C(C)C)\C(=O)O)OC(=O)C)C)C)OC(=O)C
• Molecular Weight: 568.7
• Reaxy-Rn: 37953835
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=37953835&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Steroid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Steroid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Steroid esters
• Alternative Parents: 7-oxosteroids 3-oxo-5-alpha-steroids 3-oxo delta-1-steroids Delta-1-steroids Tricarboxylic acids and derivatives Cyclohexenones Alpha-acyloxy ketones Carboxylic acid esters Carboxylic acids Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Steroid ester - 3-oxo-delta-1-steroid - 3-oxosteroid - Oxosteroid - 3-oxo-5-alpha-steroid - 7-oxosteroid - Delta-1-steroid - Tricarboxylic acid or derivatives - Cyclohexenone - Alpha-acyloxy ketone - Carboxylic acid ester - Ketone - Cyclic ketone - Carboxylic acid - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxygen compound - Carbonyl group - Organic oxide - Organooxygen compound - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
• External Descriptors: monocarboxylic acid - steroid acid - 3-oxo Delta(1)-steroid

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)

HEK293 (82097 Activities)

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A2780 (11979 Activities)

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Associated Targets(non-human)

Alternaria solani (773 Activities)

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Artemia salina (1320 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Fusarium solani (1274 Activities)

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Micrococcus luteus (7463 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Streptococcus agalactiae (1777 Activities)

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Bacillus subtilis (32866 Activities)

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Enterococcus faecalis (29875 Activities)

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Botrytis cinerea (4183 Activities)

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Alternaria alternata (757 Activities)

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Colletotrichum gloeosporioides (560 Activities)

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Fusarium oxysporum f. sp. vasinfectum (242 Activities)

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Fusarium oxysporum f. sp. niveum (47 Activities)

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Mythimna separata (3306 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO
• Sensitivity: light sensitive
• Molecular Weight: 568.700 g/mol
• XLogP3: 5.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 568.304 Da
• Monoisotopic Mass: 568.304 Da
• Topological Polar Surface Area: 124.000 Ų
• Heavy Atom Count: 41
• Formal Charge: 0
• Complexity: 1270.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1