Echinocandin B

HCID 9898144

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Basic information

CAS: 54651-05-7
Standard SMILES: CCCCC/C=C\C/C=C\CCCCCCCC(=O)N[C@H]1C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)[C@@H](C)CN2C(=O)[C@H]([C@@H](C)O)NC(=O)[C@H]([C@H](O)[C@@H](O)c2ccc(O)cc2)NC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@H]([C@@H](C)O)NC1=O
InChIKey: FAUOJMHVEYMQQG-HVYQDZECSA-N
Molecular formula: C52H81N7O16
Average molar mass: 1,060.2 g/mol
Monoisotopic mass: 1,059.57397952

Overview

Echinocandin B is a cyclic hexapeptide echinocandin antibiotic isolated from Aspergillus nidulans var. echinulatus with specific anti-yeast activity. It has a role as an antiinfective agent.

Names & identifiers

Preferred name: Echinocandin B
IUPAC: (9Z,12Z)-N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]octadeca-9,12-dienamide
English name: Echinocandin B
Molecular formula: C52H81N7O16
Molecular weight: 1060.24

Names & synonyms

Echinocandin B54651-05-7Antibiotic A 30912ACNW0ZW8ZTQANTIBIOTIC SL-7810ANTIBIOTIC A-22082A-30912 FACTOR ACHEBI:315018DTXSID301027535ANTIBIOTIC A-30912 FACTOR ANSC-287461(9Z,12Z)-N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]octadeca-9,12-dienamide

Show more names

EcbA22082A30912AA 30912AA-30912ANsc2874611)-peptideAids008606Aids-008606A 30912 factor A

(9Z,12Z)-N-((3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-((1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl)-11,20,21,25-tetrahydroxy-3,15-bis((1R)-1-hydroxyethyl)-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo(22.3.0.09,13)heptacosan-18-yl)octadeca-9,12-dienamideRefChem:136218DTXCID201513127(9Z,12Z)-N-((2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-23-((1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl)-2,11,12,15-tetrahydroxy-6,20-bis((1R)-1-hydroxyethyl)-16-methyl-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo(2,1-c:2',1'-l)(1,4,7,10,13,16)hexaazacyclohenicosin-9-yl)octadeca-9,12-dienamide;5.1:6-anhydro((4R,5R)-4,5-dihydroxy-N(2)-((9Z,12Z)-octadeca-9,12-dienoyl)-L-ornithyl-L-threonyl-(4R)-4-hydroxy-L-prolyl-(4S)-4-hydroxy-4-(4-hydroxyphenyl)-L-threonyl-L-threonyl-(3S,4S)-3-hydroxy-4-methyl-L-proline)(9Z,12Z)-N-{(2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-23-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12,15-tetrahydroxy-6,20-bis[(1R)-1-hydroxyethyl]-16-methyl-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl}octadeca-9,12-dienamide5.1:6-anhydro{(4R,5R)-4,5-dihydroxy-N(2)-[(9Z,12Z)-octadeca-9,12-dienoyl]-L-ornithyl-L-threonyl-(4R)-4-hydroxy-L-prolyl-(4S)-4-hydroxy-4-(4-hydroxyphenyl)-L-threonyl-L-threonyl-(3S,4S)-3-hydroxy-4-methyl-L-proline}Antibiotic A 22082UNII-CNW0ZW8ZTQ

Database identifiers

CAS: 54651-05-7
PubChem CID: 9898144
DTXSID: DTXSID301027535
ChEMBL: CHEMBL2374230
ChEBI: CHEBI:315018
UNII: CNW0ZW8ZTQ
EC Number: 658-057-8
Nikkaji: J363.403E

Properties

Computed structural properties

XLogP: 2.5
Topological polar surface area: 368 Å²
Hydrogen bond donors: 14
Hydrogen bond acceptors: 16
Rotatable bonds: 20
Heavy atoms: 75
Formal charge: 0
Complexity: 1,940

Physicochemical properties

Boiling point: 1384 · 1384.0±65.0 °C(Predicted)
Density: 1.37 · 1.37±0.1 g/cm3(Predicted)
storage temp.: -20 °C · Store at -20°C
solubility: DMF: Soluble; DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble
form: A powder
pka: 9.86 · 9.86±0.26(Predicted)
EWG's Food Scores: 1 · 1
FDA UNII: 0 ZW8ZTQ · CNW0ZW8ZTQ
Symbol(GHS): 7 · GHS07,GHS08
Signal word: Warning
Hazard statements: 302 · H302-H361-H319
Precautionary statements: 264 · P264-P270-P301+P312-P330-P501-P201-P202-P281-P308+P313-P405-P501-P264-P280-P305+P351+P338-P337+P313P

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P318, P330, P337+P317, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Regulatory InformationEchinocandin B: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

Signal word: Warning
Symbol(GHS): GHS07,GHS08
Hazard statements: H302-H361-H319
Precautionary statements: P264-P270-P301+P312-P330-P501-P201-P202-P281-P308+P313-P405-P501-P264-P280-P305+P351+P338-P337+P313P

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationSubstances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.

Applications · 2 items

UsesEchinocandin B is the major analogue of a family of lipopeptides isolated from several species of Aspergillus, reported in 1974. Echinocandin B is a potent antifungal and acts by inhibiting the synthesis of β-(1,3)-D-glucan, an essential component of the cell wall of susceptible fungi.

UsesEchinocandin B is a potent antifungal that acts by inhibition of the synthesis of (1,3)-D-glucan.

Suppliers52 total

武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]

广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]

广州佳途科技股份有限公司81960175-877 18933936954 · [email protected]

咸宁深蓝生物医药研发有限公司18171815831 · [email protected]

上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]

Additional notes

DefinitionChEBI: A cyclic hexapeptide echinocandin antibiotic isolated from Aspergillus nidulans var. echinulatus with specific anti-yeast activity.

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