Natural Product: ENC001551

NPs Basic Information

Download MOL File
Name
Amphotericin B
Molecular Formula C47H73NO17
IUPAC Name*
(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
SMILES
C[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@H]([C@@H](CC[C@H](C[C@H](CC(=O)O[C@H]([C@@H]([C@@H]1O)C)C)O)O)O)O)O)O)O)C(=O)O)O[C@H]3[C@H]([C@H]([C@@H]([C@H](O3)C)O)N)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
InChIKey
APKFDSVGJQXUKY-INPOYWNPSA-N
Synonyms
amphotericin b; Amphotericin; 1397-89-3; Ambisome; Amphotericine B; Fungizone; Halizon; Ampho-Moronal; Amphotericinum B; Liposomal Amphotericin B; Amfotericina B; AMPH-B; Abelcet; Amphotericin-B; Amphotec; Fungilin; Amphotocerin; Ambil; Amphotericin B liposome; amphotericin B liposomal; MFCD00877763; 7XU7A7DROE; NSC 527017; CHEBI:2682; ABELCET, LIPOSOMAL AMPHOTERICIN B; NCGC00090808-01; DSSTox_CID_2601; NSC-527017; DSSTox_RID_76653; DSSTox_GSID_22601; ABLC; Abelecet; Amphortericin B; Anfotericine B; (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-(((2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid; (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid; Amphotericin B trihydrate; IAB; UNII-7XU7A7DROE; Fungisome; Amfotericina B [INN-Spanish]; Amphotericine B [INN-French]; Amphotericinum B [INN-Latin]; CCRIS 5963; HSDB 3008; Amphotericin B [USP:INN:JAN]; Fungizone (TN); Amphotec (TN); (1S,3R,4E,6E,8E,10E,12E,14E,16E,18S,19R,20R,21S,25R,27R,30R,31R,33S,35R,37S,38R)-3-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-38-carboxylic acid; AmBisome (TN); Amp B; CAS-1397-89-3; EINECS 215-742-2; NS 718; BRN 0078342; Amphotericin b, liposome; AI3-26528; Prestwick3_000410; Amphotericin B (85%); Amphotericin B solubilized; AMPHOTERICIN B [MI]; SCHEMBL17973; AMPHOTERICIN B [INN]; AMPHOTERICIN B [JAN]; BSPBio_000340; 5-18-10-00525 (Beilstein Handbook Reference); AMPHOTERICIN B [HSDB]; BIDD:GT0351; AMPHOTERICIN B [VANDF]; BPBio1_000374; CHEMBL267345; NKTR-024; AMPHOTERICIN B [MART.]; AMPHOTERICIN B [USP-RS]; AMPHOTERICIN B [WHO-DD]; AMPHOTERICIN B [WHO-IP]; DTXSID9022601; HMS2096A22; HMS3713A22; Amphotericin B (JP17/USP/INN); HY-B0221; Amphotericin b, liposome [WHO-DD]; Amphotericin B, Streptomyces nodosus; Tox21_111027; Tox21_202484; AMPHOTERICIN B [ORANGE BOOK]; LMPK06000002; s1636; AMPHOTERICIN B [EP MONOGRAPH]; AKOS024464746; AMPHOTERICIN B [USP MONOGRAPH]; ZINC253387843; AMPHOTERICIN B LIPOSOME [VANDF]; CCG-220410; DB00681; AMPHOTERICINUM B [WHO-IP LATIN]; NCGC00260033-01; (1R-(1R*,3S*,5R*,6R*,9R*,11R*,15S*,16R*,17R*,18S*,19E,21E,23E,25E,27E,29E,31E,33R*,35S*,36R*,37S*))-33-((3-Amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy)-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo(33.3.1)nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid; 14,39-Dioxabicyclo(33.3.1)nonatriaconta-19,21,23,25,2 7,29,31-heptaene-36-carboxylic acid, 33-((3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy)-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-(1R-(1R*,3S*,5R*,6R*,9R*,11R*,15S*,16R*,17R*,18S*,19E,21E,23E, 25E-27E,29E,31E,33R*,35S*,36R*,37S*))-; AB00513832; C06573; D00203; AB00513832_02; 397A893; Q412223; 1397-89-3, C47H73NO17; Amphotericin B from Streptomyces sp., ~80% (HPLC), powder; Amphotericin B from Streptomyces sp., BioReagent, suitable for cell culture, ~80% (HPLC); Amphotericin B solubilized, powder, gamma-irradiated, BioXtra, suitable for cell culture; (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,; (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid; (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(3-Amino-3,6-dideoxy-?-D-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid; (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-he; (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(3-amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-hept; (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,33R,35S,36R,37S)-33-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carbo; (1S,3R,4E,6E,8E,10E,12E,14E,16E,18S,19R,20R,21S,25R,27R,30R,31R,33S,35R,37S,38R)-3-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-; 23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,12,14,16-heptaene-38-carboxylic acid; Amphotericin B from Streptomyces sp., Vetec(TM) reagent grade, BioReagent, suitable for cell culture, ~80%
CAS 1397-89-3; 3065
PubChem CID 5280965
ChEMBL ID CHEMBL267345
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Organic oxygen compounds
      • Class: Organooxygen compounds
        • Subclass: Carbohydrates and carbohy
          • Direct Parent: Aminoglycosides

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference
Endophyte ID Endophyte Name Family Genus Taxonomy ID GenBank ID Closest GenBank ID Reference

NPs Content

*Note: The vaules in Content Percentage are calculated by dividing the content value by the maximum content value in NP Content.
**Note: The units with different NP content, due to their incomparable values, are separated into different tables.

NPs Biological Activity

Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name
Bioactivity Name Target ID Target Name Target Type Target Organism Target Organism ID Potency of Bioactivity Activity Type Value Unit Endophyte ID Endophyte Name

NPs Physi-Chem Properties

Molecular Weight: 924.1 ALogp: 0.0
HBD: 12 HBA: 18
Rotatable Bonds: 3 Lipinski's rule of five: Rejected
Polar Surface Area: 320.0 Aromatic Rings: 3
Heavy Atoms: 65 QED Weighted: 0.177

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -5.891 MDCK Permeability: 0.00008830
Pgp-inhibitor: 0 Pgp-substrate: 0.724
Human Intestinal Absorption (HIA): 0.815 20% Bioavailability (F20%): 0.999
30% Bioavailability (F30%): 1

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.171 Plasma Protein Binding (PPB): 33.67%
Volume Distribution (VD): 0.193 Fu: 4.62%

ADMET: Metabolism

CYP1A2-inhibitor: 0.03 CYP1A2-substrate: 0.006
CYP2C19-inhibitor: 0.06 CYP2C19-substrate: 0.067
CYP2C9-inhibitor: 0.001 CYP2C9-substrate: 0.993
CYP2D6-inhibitor: 0.007 CYP2D6-substrate: 0.512
CYP3A4-inhibitor: 0.097 CYP3A4-substrate: 0.054

ADMET: Excretion

Clearance (CL): 0.76 Half-life (T1/2): 0.488

ADMET: Toxicity

hERG Blockers: 0.509 Human Hepatotoxicity (H-HT): 0.978
Drug-inuced Liver Injury (DILI): 0.744 AMES Toxicity: 0.079
Rat Oral Acute Toxicity: 0.025 Maximum Recommended Daily Dose: 0.997
Skin Sensitization: 0.876 Carcinogencity: 0.29
Eye Corrosion: 0.003 Eye Irritation: 0.01
Respiratory Toxicity: 0.968
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

Similar NPs Similar Drugs
NPs ID NPs 2D Structure Similarity Score TTD ID Drug 2D Structure Similarity Score
ENC003810 0.351 D02DWM 1.000
ENC004058 0.348 D08XAC 0.834
ENC003127 0.305 D0I6IP 0.556
ENC001476 0.260 D02FEM 0.551
ENC002797 0.257 D0F5OR 0.281
ENC0049112 0.250 D0P2IT 0.279
ENC003461 0.248 D0P6IK 0.269
ENC002265 0.240 D07TGN 0.268
ENC003286 0.239 D07ORO 0.267
ENC003639 0.230 D0AR3J 0.262
*Note: the compound similarity was calculated by RDKIT.