Friulimicin B

Identification

Generic Name

Friulimicin B

DrugBank Accession Number

DB06087

Background

Friulimicin B是一个naturally occurring antibiotic produced by a micro-organism,Actinoplanes friuliensis. It shows strong cidal activity against a number of Gram-positive pathogens which commonly cause serious infections in hospital patients and which are becoming more routinely acquired in the community.

Type

Small Molecule

Groups

Investigational

Structure

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MOL SDF PDB SMILES InChI

类似Structures

Structure for Friulimicin B (DB06087)

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Weight

Average: 1303.48
Monoisotopic: 1302.681966863

Chemical Formula

C₅₉H₉₄N₁₄O₁₉

同义词

• Friulimycin B

External IDs

• A 1437 delta

Pharmacology

Indication

Investigated for use/treatment in bacterial infection.

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Not Available

Mechanism of action

Friulimicin B, in the presence of calcium, forms a complex with a lipid carrier that acts in cell wall biosynthesis and which is not targeted by other antibiotics currently in use. Friulimicin B appears to block two essential pathways in the cell envelope and the complexes formed prevent the formation of a functional cell wall.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

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Not Available

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Not Available

Food Interactions

Not Available

Categories

Drug Categories

• Amino Acids, Peptides, and Proteins

Chemical TaxonomyProvided byClassyfire

Description

This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

有机化合物

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Cyclic peptides/Asparagine and derivatives/Macrolactams/N-acyl-alpha amino acids and derivatives/Alpha amino acid amides/Beta amino acids and derivatives/Tricarboxylic acids and derivatives/Piperidines/N-acyl amines/Tertiary carboxylic acid amides /Pyrrolidines/Lactams/Primary carboxylic acid amides/Secondary carboxylic acid amides/Amino acids/Carboxylic acids/Azacyclic compounds/Monoalkylamines/Hydrocarbon derivatives/Carbonyl compounds/Organic oxides

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Substituents

Aliphatic heteropolycyclic compound/Alpha-amino acid amide/Alpha-amino acid or derivatives/Alpha-oligopeptide/Amine/Amino acid/Amino acid or derivatives/Asparagine or derivatives/Azacycle/Beta amino acid or derivatives /Carbonyl group/Carboxamide group/Carboxylic acid/Cyclic alpha peptide/Fatty acyl/Fatty amide/Hydrocarbon derivative/Lactam/Macrolactam/N-acyl-alpha amino acid or derivatives/N-acyl-amine/N-substituted-alpha-amino acid/Organic nitrogen compound/Organic oxide/Organic oxygen compound/Organoheterocyclic compound/Organonitrogen compound/Organooxygen compound/Piperidine/Primary aliphatic amine/Primary amine/Primary carboxylic acid amide/Pyrrolidine/Secondary carboxylic acid amide/Tertiary carboxylic acid amide/Tricarboxylic acid or derivatives

show 26 more

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Affected organisms

Not Available

Chemical Identifiers

UNII

AYO43961I1

CAS number

239802-15-4

InChI Key

HVYFVLAUKMGKHL-USKUEUQVSA-N

InChI

InChI=1S/C59H94N14O19/c1-30(2)19-14-12-10-8-9-11-13-15-22-41(75)65-35(25-40(61)74)52(84)71-49-34(7)64-53(85)39-21-18-24-73(39)57(89)46(31(3)4)69-56(88)48(33(6)60)68-43(77)29-63-50(82)36(26-44(78)79)66-42(76)28-62-51(83)37(27-45(80)81)67-55(87)47(32(5)59(91)92)70-54(86)38-20-16-17-23-72(38)58(49)90/h13,15,30-39,46-49H,8-12,14,16-29,60H2,1-7H3,(H2,61,74)(H,62,83)(H,63,82)(H,64,85)(H,65,75)(H,66,76)(H,67,87)(H,68,77)(H,69,88)(H,70,86)(H,71,84)(H,78,79)(H,80,81)(H,91,92)/b15-13-/t32-,33+,34-,35-,36-,37-,38+,39-,46-,47-,48+,49-/m0/s1

IUPAC Name

(2S)-2-[(3S,4S,7S,13S,16R,22S,28S,31S,34R)-16-[(1R)-1-aminoethyl]-3-[(2S)-3-carbamoyl-2-[(3Z)-12-methyltridec-3-enamido]propanamido]-22,28-bis(carboxymethyl)-4-methyl-2,6,12,15,18,21,24,27,30,33-decaoxo-13-(propan-2-yl)-1,5,11,14,17,20,23,26,29,32-decaazatricyclo[32.4.0.0^{7,11}]octatriacontan-31-yl]propanoic acid

SMILES

CC(C)CCCCCCC\C=C/CC(=O)N[C@@H](CC(N)=O)C(=O)N[C@H]1[C@H](C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H]2CCCCN2C1=O)[C@H](C)C(O)=O)[C@@H](C)N)C(C)C

References

General References

1. Muller C, Nolden S, Gebhardt P, Heinzelmann E, Lange C, Puk O, Welzel K, Wohlleben W, Schwartz D: Sequencing and analysis of the biosynthetic gene cluster of the lipopeptide antibiotic Friulimicin in Actinoplanes friuliensis. Antimicrob Agents Chemother. 2007 Mar;51(3):1028-37. Epub 2007 Jan 12. [Article]
2. Heinzelmann E, Berger S, Puk O, Reichenstein B, Wohlleben W, Schwartz D: A glutamate mutase is involved in the biosynthesis of the lipopeptide antibiotic friulimicin in Actinoplanes friuliensis. Antimicrob Agents Chemother. 2003 Feb;47(2):447-57. [Article]
3. Vertesy L, Ehlers E, Kogler H, Kurz M, Meiwes J, Seibert G, Vogel M, Hammann P: Friulimicins: novel lipopeptide antibiotics with peptidoglycan synthesis inhibiting activity from Actinoplanes friuliensis sp. nov. II. Isolation and structural characterization. J Antibiot (Tokyo). 2000 Aug;53(8):816-27. [Article]

External Links

ChemSpider

32699135

Wikipedia

Friulimicin

Clinical Trials

Clinical TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
1	Terminated	Treatment	Community Acquired Pneumonia (CAP)/Staphylococcal Skin Infections	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0161 mg/mL	ALOGPS
logP	-0.5	ALOGPS
logP	-7.2	Chemaxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	3.08	Chemaxon
pKa (Strongest Basic)	8.33	Chemaxon
Physiological Charge	-2	Chemaxon
Hydrogen Acceptor Count	20	Chemaxon
Hydrogen Donor Count	15	Chemaxon
Polar Surface Area	512.63 Å2	Chemaxon
Rotatable Bond Count	23	Chemaxon
Refractivity	321.78 m3·mol-1	Chemaxon
Polarizability	134.16 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Not Available

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Drug created at November 18, 2007 18:29 / Updated at June 12, 2020 16:52