Herbimycin A - Moligand™, ≥95% , CAS No.70563-58-5

CAS: 70563-58-5 Cat. No.: H102384 Formula: C₃₀H₄₂N₂O₉ Molecular Weight: 574.66 Beilstein Registry Number: 4834067

GRADE & PURITY Moligand™, ≥95%

Synonyms

UNII-815WDV2HST | Antibiotic Tan 420F | SCHEMBL32882 | ACon0_000819 | 815WDV2HST | Geldanamycin, 17-demethoxy-15-methoxy-11-O-methyl-, (15R)- | (4E,6Z,8S,9S,10E,12S,13R,14S,16S,17R)-8,13,14,17-tetramethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicycl

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Product Describtion:

Herbimycin A, an ansamycin antibiotic, acts as a Src family kinase inhibitor. Herbimycin A binds to the SH domain and inhibits the activity of p60v-src and p210BCR-ABL Herbimycin A inhibits Hsp90 and impairs recovery from heat shock. Herbimycin A exhibits antiangiogenic activity in endothelial cells in vitro.

Specifications

Synonyms

UNII-815WDV2HST | Antibiotic Tan 420F | SCHEMBL32882 | ACon0_000819 | 815WDV2HST | Geldanamycin, 17-demethoxy-15-methoxy-11-O-methyl-, (15R)- | (4E,6Z,8S,9S,10E,12S,13R,14S,16S,17R)-8,13,14,17-tetramethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicycl

Specifications & Purity

Moligand™, ≥95%

Biochemical and Physiological Mechanisms

Cell-permeable Src tyrosine kinase inhibitor and ansamycin antibiotic. Binds to the SH domain and inhibits p60 v-src and p210 BCR-ABL activity. Specific IKKβ and angiogenesis inhibitor. Anti-bacterial, anti-inflammatory and antitumor effects. Active in vi

Source

Isolated from Streptomyces sp.

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

Moligand™

Action Type

INHIBITOR

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

≥95%

Names and Identifiers

Canonical Smiles

CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C=C(C1OC)C2=O)C)OC)OC(=O)N)C)C)OC)OC

IUPAC Name

[(4E,6Z,8S,9S,10E,12S,13R,14S,16S,17R)-8,13,14,17-tetramethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate

InChIKey

MCAHMSDENAOJFZ-BVXDHVRPSA-N

INCHI

1S/C30H42N2O9/c1-16-10-9-11-23(37-5)28(41-30(31)36)18(3)12-17(2)27(40-8)24(38-6)13-19(4)26(39-7)21-14-20(33)15-22(25(21)34)32-29(16)35/h9-12,14-15,17,19,23-24,26-28H,13H2,1-8H3,(H2,31,36)(H,32,35)/b11-9-,16-10+,18-12+/t17-,19-,23-,24-,26+,27+,28-/m0/s1

Isomeric SMILES

C[C@H]1C[C@@H]([C@@H]([C@H](/C=C(/[C@@H]([C@H](/C=C\C=C(\C(=O)NC2=CC(=O)C=C([C@@H]1OC)C2=O)/C)OC)OC(=O)N)\C)C)OC)OC

WGK Germany

3

RTECS

LX8930000

Molecular Weight

574.66

Beilstein

4834067

Reaxy-Rn

26268490

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=26268490&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Macrolactams

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Macrolactams
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Macrolactams
• Alternative Parents: Vinylogous amides Carbamate esters Secondary carboxylic acid amides Organic carbonic acids and derivatives Lactams Cyclic ketones Dialkyl ethers Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Macrolactam - Carbamic acid ester - Vinylogous amide - Carboxamide group - Ketone - Lactam - Carbonic acid derivative - Secondary carboxylic acid amide - Cyclic ketone - Carboxylic acid derivative - Dialkyl ether - Ether - Azacycle - Organoheterocyclic compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Carbonyl group - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
• External Descriptors: lactam - macrocycle - benzoquinones

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in ethanol, methanol DMSO or dimethylformamide. Poorly soluble in water.
• Sensitivity: light sensitive
• Molecular Weight: 574.700 g/mol
• XLogP3: 1.800
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 574.289 Da
• Monoisotopic Mass: 574.289 Da
• Topological Polar Surface Area: 152.000 Ų
• Heavy Atom Count: 41
• Formal Charge: 0
• Complexity: 1150.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 7
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 3
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 3
• Covalently-Bonded Unit Count: 1