AMPHOTERICIN B

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category Free-form
ATC A01AB04 A07AA07 G01AA03 J02AA01
UNII 7XU7A7DROE
EPA CompTox DTXSID9022601

Structure

InChI Key APKFDSVGJQXUKY-INPOYWNPSA-N
Smiles C[C@@H]1[C@H](O)[C@@H](C)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H](N)[C@@H]2O)C[C@@H]2O[C@](O)(C[C@@H](O)C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)CC(=O)O[C@H]1C)C[C@H](O)[C@H]2C(=O)O
InChI
InChI=1S/C47H73NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C47H73NO17
Molecular Weight 924.09
AlogP 0.71
Hydrogen Bond Acceptor 17.0
Hydrogen Bond Donor 12.0
Number of Rotational Bond 3.0
Polar Surface Area 319.61
Molecular species ZWITTERION
Aromatic Rings 0.0
Heavy Atoms 65.0

Pharmacology

Mechanism of Action Action Reference
Ergosterol sequestering agent SEQUESTERING AGENT PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - - 8.91-11.88
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 89.01-99.53
EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Aspergillus flavus
- - - - 86.4
Aspergillus fumigatus
- 1-900 - - -
Aspergillus niger
- 900 - - 79.9
Candida albicans
- 30-720 - - 100-100
Candida albicans SC5314
- 500 - - -
Candida glabrata
- 200-460 - - 100
Candida parapsilosis
- 300 - - 100
Candida tropicalis
- 100-300 - - 100
Chlorocebus sabaeus
- 330 - - -
Cricetulus griseus
- - - - 89.01-99.53
Cryptococcus neoformans
- 0.2-920 - - 100-100
Electrophorus electricus
- - - - 8.91
Equus caballus
- - - - 11.88
Fusarium oxysporum
- - - - 0-99.7
Fusarium solani
- - - - 0-100
Gibberella intermedia
- - - - 0-99.8
Human immunodeficiency virus 1
- 136-175 - - -
Leishmania aethiopica
- 110 - - -
Leishmania amazonensis
24-330 60-900 - - -
Leishmania braziliensis
800 90-300 - - -
Leishmania braziliensis MHOM/BR/75/M2904
- 300-300 - - -
Leishmania chagasi
- 10-690 - - -
Leishmania donovani
10-280 0-770 - - 78.6-99
Leishmania infantum
50-920 0-900 - - 95.5
Leishmania major
35-320 0.035-600 - - 69.9-79.8
Leishmania martiniquensis
- 31 - - 94.2-97.5
Leishmania mexicana
- 80-280 - - 99
Leishmania orientalis
- 23-108 - - 91.1-96.7
Leishmania panamensis
54 70 - - 76
Leishmania peruviana
- 100-100 - - -
Leishmania tropica
- 90-160 - - -
Mus musculus
- 520 - - -
Naegleria fowleri
- 18.3-200 - - 100
Pichia kudriavzevii
- 200-850 - - 100
Pyricularia oryzae
- 160 - - -
Saccharomyces cerevisiae
- 550-550 - - -
Trichophyton mentagrophytes
- 540-900 - - -
Trichophyton rubrum
- 600-600 - - -
Trypanosoma cruzi
- 152-230 - - -
trypanosoma infantum
- 50 - - -

Related Entries

Cross References

Resources Reference
ChEBI 2682
ChEMBL CHEMBL267345
DrugBank DB00681
DrugCentral 197
FDA SRS 7XU7A7DROE
Human Metabolome Database HMDB0014819
KEGG C06573
PharmGKB PA448415
PubChem 5280965
SureChEMBL SCHEMBL17973
ZINC ZINC000253387843
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