Rifamycin S - ≥97% , CAS No.13553-79-2

CAS: 13553-79-2 Cat. No.: R302471 Molecular Weight: 695.76 EC Number: 236-938-4 PubChem CID: 6436726

GRADE & PURITY ≥97%

Synonyms

(R)-Ethyl 3-hydroxybutyrate | EINECS 236-938-4 | RIFAMYCIN SODIUM IMPURITY B [EP IMPURITY] | 1,4-Dideoxy-1,4-dihydro-1,4-dioxorifamycin | Rafamycin S | BRN 0604802 | Rifamycin S | NCGC00182056-03 | AI3-18917 | NCI 144-130 | [(7S,9E,11S,12R,13S,14R,15R,16R

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Rifamycin S is a quinone and an antibiotic agnet against Gram-positive bacteria (including MRSA). Rifamycin S is the oxidized forms of a reversible oxidation-reduction system involving two electrons. Rifamycin S generates reactive oxygen species (ROS) and inhibits microsomal lipid peroxidation. Rifamycin S can be used for tuberculosis and leprosy.

Specifications

Synonyms

(R)-Ethyl 3-hydroxybutyrate | EINECS 236-938-4 | RIFAMYCIN SODIUM IMPURITY B [EP IMPURITY] | 1, 4-Dideoxy-1, 4-dihydro-1, 4-dioxorifamycin | Rafamycin S | BRN 0604802 | Rifamycin S | NCGC00182056-03 | AI3-18917 | NCI 144-130 | [(7S, 9E, 11S, 12R, 13S, 14R, 15R, 16R

Specifications & Purity

≥97%

Storage

Store at 2-8°C

Shipped In

Wet ice

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

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 504764170
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504764170
• Canonical Smiles: CC1C=CC=C(C(=O)NC2=CC(=O)C3=C(C2=O)C(=C(C4=C3C(=O)C(O4)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C)O)C
• IUPAC Name: [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl] acetate
• InChIKey: BTVYFIMKUHNOBZ-ODRIEIDWSA-N
• INCHI: 1S/C37H45NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,41-43H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1
• Isomeric SMILES: C[C@H]1/C=C/C=C(\C(=O)NC2=CC(=O)C3=C(C2=O)C(=C(C4=C3C(=O)[C@](O4)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)/C
• PubChem CID: 6436726
• Molecular Weight: 695.76

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: Naphthofurans Naphthoquinones Benzofurans Coumarans Quinones Aryl alkyl ketones Ketals Vinylogous amides Vinylogous acids Secondary carboxylic acid amides Secondary alcohols Carboxylic acid esters Lactams Polyols Azacyclic compounds Oxacyclic compounds Dialkyl ethers Monocarboxylic acids and derivatives Organopnictogen compounds Hydrocarbon derivatives Organic oxides Organonitrogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Naphthofuran - Macrolactam - Naphthoquinone - Naphthalene - Benzofuran - Coumaran - Aryl alkyl ketone - Aryl ketone - Quinone - Ketal - Benzenoid - Vinylogous amide - Vinylogous acid - Lactam - Carboxylic acid ester - Carboxamide group - Secondary carboxylic acid amide - Secondary alcohol - Ketone - Acetal - Carboxylic acid derivative - Dialkyl ether - Ether - Oxacycle - Monocarboxylic acid or derivatives - Azacycle - Organoheterocyclic compound - Polyol - Organic nitrogen compound - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organic oxygen compound - Alcohol - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Aromatic 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: Ansamycins and related polyketides

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(non-human)

rpoB DNA-directed RNA polymerase beta chain (70 Activities)

Discover Target: rpoB

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

Streptococcus pneumoniae (31063 Activities)

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Staphylococcus aureus (210822 Activities)

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Neisseria gonorrhoeae (1461 Activities)

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Escherichia coli (133304 Activities)

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Haemophilus influenzae (8812 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: heat sensitive
• Specific Rotation[α]: 476° (C=0.1,MeOH)
• Melt Point(°C): 201 °C
• Molecular Weight: 695.800 g/mol
• XLogP3: 4.100
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 3
• Exact Mass: 695.294 Da
• Monoisotopic Mass: 695.294 Da
• Topological Polar Surface Area: 195.000 Ų
• Heavy Atom Count: 50
• Formal Charge: 0
• Complexity: 1480.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• 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

References

1. Jiahang Liu, Yingying Chu, Xiaoyang Li, Mengying Qian, Weiming Zhang.  (2025)  An Fe(III)/H2O2 Fenton-like process enhanced by Rifampicin: The role of hydroquinone moiety.  ENVIRONMENTAL RESEARCH,      [PMID:40983274] [10.1016/j.envres.2025.122922]