Select a section from the left sidebar
Amphotericin B
- Family: Plantae - Asteraceae
- Kingdom: Plantae
- Class: Polyene
| Canonical Smiles | O[C@@H]1CC[C@@H](O)[C@H](O)C[C@H](O)C[C@]2(O)C[C@H](O)[C@H]([C@@H](O2)C[C@H](/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H]([C@H]([C@H]([C@@H](OC(=O)C[C@@H](C1)O)C)C)O)C)O[C@@H]1O[C@H](C)[C@H]([C@@H]([C@@H]1O)N)O)C(=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 |
| InChIKey | APKFDSVGJQXUKY-INPOYWNPSA-N |
| Formula | C47H73NO17 |
| HBA | 17 |
| HBD | 12 |
| MW | 924.09 |
| Rotatable Bonds | 3 |
| TPSA | 319.61 |
| LogP | 0.71 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 65 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.66 |
| Exact Mass | 923.49 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Vernonia urticifolia | Asteraceae | Plantae | 3032568 |
| 2 | Vernonia urticifolia | Asteraceae | Plantae | 3032568 |
Showing of synonyms
Amphotericin B
1397-89-3
Amphotericine B
Fungizone
Halizon
Amfotericina B
Ampho-Moronal
Amphotericinum B
Amphocin
Amphotec
Fungilin
Amphozone
AMPH-B
Amphotocerin
Abelecet
ABLC
Ambil
Anfotericine B
Amphotericin B liposome
Mysteclin-F
UNII-7XU7A7DROE
7XU7A7DROE
CCRIS 5963
CHEBI:2682
HSDB 3008
EINECS 215-742-2
NS 718
NSC 527017
BRN 0078342
ABELCET, LIPOSOMAL AMPHOTERICIN B
Fungisone
AI3-26528
Amfotericina B [INN-Spanish]
Amphotericine B [INN-French]
Amphotericinum B [INN-Latin]
Amphotericin B [USP:INN:JAN]
5-18-10-00525 (Beilstein Handbook Reference)
NSC-527017
(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*))-
Amfotericina B (INN-Spanish)
Amphotericine B (INN-French)
Amphotericinum B (INN-Latin)
AMPHOTERICIN B (MART.)
AMPHOTERICIN B [MART.]
AMPHOTERICIN B (USP-RS)
AMPHOTERICIN B [USP-RS]
Amphotericin B (USP:INN:JAN)
Amphomoronal
AMPHOTERICIN B (EP MONOGRAPH)
AMPHOTERICIN B [EP MONOGRAPH]
NSC527017
AMPHOTERICIN B (USP MONOGRAPH)
AMPHOTERICIN B [USP MONOGRAPH]
IAB
(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
DTXCID802601
DTXSID9022601
Funganiline
Amphotericin BETA
(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
AMPHOTERACIN B
A01AB04
A07AA07
G01AA03
J02AA01
14,39-Dioxabicyclo(33.3.1)nonatriaconta-19,21,23,25,27,29,31-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,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-
(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-mannopyranosyloxy)-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,36S,37S)-33-(3-Amino-3,6-dideoxy-beta-D-mannopyranosyloxy)-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-19,21,23,25,27,29,31-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,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S
14,39-DIOXABICYCLO(33.3.1)NONATRIACONTA-19,21,23,25,27,29,31-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*))-
215-742-2
1397-89-330652-87-0
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*))-
Amphotericin
Ambisome
MFCD00877763
Amphotericin-B
Amphotericin B liposomal
Amphotericin B (85%)
Amphotericin B (~80%)
Amphortericin 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-[(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
Amphotericin B trihydrate
Fungisome
Amphotericin B?
Fungizone (TN)
NCGC00090808-01
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
(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-ss-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
AmBisome (TN)
Amp B
Amphotericin b, liposome
Prestwick3_000410
Amphotericin B solubilized
Amphotericin B (Standard)
AMPHOTERICIN B [MI]
SCHEMBL17973
AMPHOTERICIN B [INN]
AMPHOTERICIN B [JAN]
BSPBio_000340
AMPHOTERICIN B [HSDB]
BIDD:GT0351
AMPHOTERICIN B [VANDF]
BPBio1_000374
CHEMBL267345
NKTR-024
AMPHOTERICIN B [WHO-DD]
AMPHOTERICIN B [WHO-IP]
HY-B0221R
HMS2096A22
HMS3713A22
Amphotericin B (JP18/USP/INN)
Amphotericin B - Bio-X trade mark
HY-B0221
Amphotericin b, liposome [WHO-DD]
Amphotericin B, Streptomyces nodosus
AMPHOTERICIN B [ORANGE BOOK]
Amphotericin B from Streptomyces sp.
LMPK06000002
S1636
AKOS024464746
AA15700
AMPHOTERICIN B LIPOSOME [VANDF]
CCG-220410
DB00681
AMPHOTERICINUM B [WHO-IP LATIN]
AA161113
A2114
AB00513832
C06573
D00203
AB00513832_02
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-[(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,19Z,21Z,23Z,25Z,27Z,29Z,31Z,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
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*))-
4UH
Amphotericin B from Streptomyces sp., Vetec(TM) reagent grade, BioReagent, suitable for cell culture, ~80%
- Kiplimo JJ, Everia CA, et al. (2011). Novel polyene from Vernonia urticifolia (Asteraceae). Journal of Medicinal Plants Research,2011,5(17),4202-4211. [View] [PubMed]
- Kiplimo JJ, Koorbanally NA. (2012). The phytochemistry and biological activity of secondary metabolites from Kenyan Vernonia and Vepris species. PhD Thesis, University of Kwazulu-Natal, South Africa,2012. [View] [PubMed]
Pubchem:
5280965
Cas:
1397-89-3
Gnps:
CCMSLIB00000478123
Zinc:
ZINC000253387843
Kegg Ligand:
C06573
Chebi:
2682
Nmrshiftdb2:
60058697
Metabolights:
MTBLC2682
Chembl:
CHEMBL267345
Comptox:
DTXSID9022601
Drugbank:
DB00681
Pdb Ligand:
4UH
Bindingdb:
50457967
CPRiL:
901
SMILES: C12CCCC(O2)CCCCCCCCCCCC(=O)OCCCCC=CC=CC=CC=CC=CC=CC=CC(C1)OC3CCCCO3
Level: 1
Mol. Weight: 924.09 g/mol
SMILES: C12CCCC(O2)CCCCCCCCCCCC(=O)OCCCCC=CC=CC=CC=CC=CC=CC=CCC1
Level: 0
Mol. Weight: 924.09 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 924.09 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.36
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 630.34
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 83319.7
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.32
- Plasma Protein Binding
- 74.5
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 0.38
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Safe
- Bioconcentration Factor
- -1936.5
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.01
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.89
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -151230751.31
- Rat (Acute)
- 2.3
- Rat (Chronic Oral)
- 3.32
- Fathead Minnow
- 190904.68
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 17004668.49
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- -1.27
- Log(P)
- -0.53
- Log S
- -1.71
- Log(Vapor Pressure)
- -559801.42
- Melting Point
- 218.75
- pKa Acid
- -3991.16
- pKa Basic
- 9.52
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.8476 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.8476 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8381 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8381 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7785 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7785 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7649 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7649 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7514 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7514 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7430 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7430 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7380 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7380 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7212 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7212 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7120 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7120 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7099 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7099 |
| Lactaldehyde dehydrogenase | P25553 | ALDA_ECOLI | Escherichia coli | 3 | 0.7045 |
| Lactaldehyde dehydrogenase | P25553 | ALDA_ECOLI | Escherichia coli | 3 | 0.7045 |