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Borrelidin

Borrelidin structure

CAS No:
7184-60-3
Formula:
C28H43NO6
Chemical Name:
Borrelidin
Synonyms:
Cyclopentanecarboxylic acid,2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]-,(1R,2R)-;Cyclopentanecarboxylic acid,2-(7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl)-,[2S-[2R*(1S*,2S*),4E,6Z,8S*,9R*,11S*,13R*,15R*,16R*]]-;Borrelidin;Oxacyclooctadecane,cyclopentanecarboxylic acid deriv.;(1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]cyclopentanecarboxylic acid;Borrelidine;Treponemycin;NSC 216128;(-)-Borrelidin;B 3061;Borrelidin A;97328-74-0;1403-11-8
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Borrelidin (Treponemycin) is a nitrile-containing macrolide antibiotic isolated from Streptomyces rochei, which acts as an inhibitor of bacterial and eukaryal threonyl-tRNA synthetase, can target ALL cell lines by inducing apoptosis and mediating G(1) arrest. Borrelidin (Treponemycin) is an inhibitor of a cyclin-dependent kinase (CDK) of the budding yeast, Cdc28/Cln2 with an IC50 of 24 μM. Borrelidin (Treponemycin) is a potent angiogenesis inhibitor with an IC50 of 0.8 nM for capillary t

Borrelidin Basic Attributes

Molecular Weight：

489.64

Exact Mass：

489.64

HScode：

29419090

Characteristics

PSA：

127.85000

XLogP3：

4.31

Density：

1.1±0.1 g/cm3

Melting Point：

93-95 °C

Boiling Point：

710.3±60.0 °C at 760 mmHg

Flash Point：

383.4±32.9 °C

Refractive Index：

1.539

Water Solubility：

DMSO: 1 mg/mL

Storage Conditions：

−20°C

Toxicity：

Subcutaneous-rat LD50: 1.780 mg/kg; subcutaneous-mouse LD50: 75 mg/kg

Flammability characteristics：

Thermal decomposition to emit toxic nitrogen oxide fumes

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

safety instructions：

24/25

RTECS Number：

ED8750000

Storage features：

The warehouse is ventilated, low temperature and dry, and stored separately from food materials

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Toxicity

Toxicity class：

most toxic

Drug Information

MeSH Entry Terms：

borrelidin|treponemycin

Borrelidin Use and Manufacturing

Borrelidin is a secondary metabolite produced by Streptomyces and other bacteria. It displays potent antiangiogenic activity, preventing tube formation in rat aorta explants (IC50 = 0.8 nM) and inducing apoptosis in endothelial cells. Borrelidin also alters the splicing of VEGF mRNA, producing an antiangiogenic isoform of the growth factor. It has long been known as a powerful inhibitor of both eukaryotic and bacterial threonyl tRNA synthetase. Borrelidin is also an effective anti-malarial drug, as it kills P. falciparum with an IC50 value of 1.8 nM. At higher doses, it inhibits cyclin-dependent kinase in yeast (IC50 = 24 μM), resulting in growth arrest in the G1 phase.

Computed Properties

Molecular Weight:489.6
XLogP3:5.6
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:2
Exact Mass:489.30903809
Monoisotopic Mass:489.30903809
Topological Polar Surface Area:128
Heavy Atom Count:35
Complexity:827
Defined Atom Stereocenter Count:9
Undefined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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2-(7-CYANO-8,16-DIHYDROXY-9,11,13,15-TETRAMETHYL-18-OXOOXACYCLOOCTADECA-4,6-DIEN-2-YL)-CYCLOPENTANECARBOXYLIC ACID

CAS No.: 7184-60-3

Grade: Industrial Grade

Content: 98%

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Borrelidin

CAS No.: 7184-60-3

Content: 99%

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