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Nigericin
- Family: Monera - Streptomycetaceae
- Kingdom: Monera
-
Class: Ether
- Subclass: Polycyclic Ether
| Canonical Smiles | CO[C@@H]1C[C@@H](C[C@H]2CC[C@@H]([C@@H](O2)[C@H](C(=O)O)C)C)O[C@@]2([C@@H]1C)O[C@](C[C@H]2C)(C)[C@H]1CC[C@@](O1)(C)[C@@H]1O[C@H](C[C@@H]1C)[C@H]1O[C@@](O)(CO)[C@@H](C[C@@H]1C)C |
|---|---|
| InChI | InChI=1S/C40H68O11/c1-21-11-12-28(46-33(21)26(6)36(42)43)17-29-18-30(45-10)27(7)40(48-29)25(5)19-38(9,51-40)32-13-14-37(8,49-32)35-23(3)16-31(47-35)34-22(2)15-24(4)39(44,20-41)50-34/h21-35,41,44H,11-20H2,1-10H3,(H,42,43)/t21-,22-,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,37-,38-,39-,40+/m0/s1 |
| InChIKey | DANUORFCFTYTSZ-SJSJOXFOSA-N |
| Formula | C40H68O11 |
| HBA | 10 |
| HBD | 3 |
| MW | 724.97 |
| Rotatable Bonds | 9 |
| TPSA | 142.37 |
| LogP | 5.71 |
| Number Rings | 6 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 51 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.97 |
| Exact Mass | 724.48 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Streptomyces youssoufiensis | Streptomycetaceae | Monera | 654447 |
Showing of synonyms
Nigericin
Azalomycin M
28380-24-7
Helixin C
Antibiotic X-464
UNII-RRU6GY95IS
RRU6GY95IS
BRN 1696755
CHEBI:7569
X-464
NIGERICIN [MI]
DTXSID9041079
(2R)-2-[(2R,3S,6R)-6-{[(2S,4R,5R,7R,9R,10R)-2-{(2S,2'R,3'S,5R,5'R)-5'-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl]-2,3'-dimethyloctahydro-2,2'-bifuran-5-yl}-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]dec-7-yl]methyl}-3-methyltetrahydro-2H-pyran-2-yl]propanoic acid
(2R)-2-[(2R,3S,6R)-6-[[(2S,4R,5R,6R,7R,9R)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyloxan-2-yl]propanoic acid
(2R)-2-((2R,3S,6R)-6-(((2S,4R,5R,6R,7R,9R)-2-((2R,5S)-5-((2R,3S,5R)-5-((2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl)-3-methyloxolan-2-yl)-5-methyloxolan-2-yl)-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro(4.5)decan-9-yl)methyl)-3-methyloxan-2-yl)propanoic acid
(2R)-2-((2R,3S,6R)-6-(((2S,4R,5R,7R,9R,10R)-2-((2S,2'R,3'S,5R,5'R)-5'-((2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-2,3'-dimethyloctahydro-2,2'-bifuran-5-yl)-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro(4.5)dec-7-yl)methyl)-3-methyltetrahydro-2H-pyran-2-yl)propanoic acid
DTXCID7021079
686-881-8
28643-80-3
Antibiotic K 178
Helix C
NSC292567
BSPBio_001599
SCHEMBL149611
CHEMBL405862
HMS1791P21
HMS1989P21
HMS3402P21
Antibiotic K178
Antibiotic X464
DBA38024
CA-421
AKOS040742303
DB14056
NCGC00163412-02
HY-127019
CS-0091495
NS00010273
SR-05000002332
Q7033077
SR-05000002332-2
(2R)-2-((3S)-6-{[2-((5S)-5-{(3S)-5-[(3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethylperhydro-2H-pyran-2-yl]-3-methyloxolan-2-yl}-5-methyloxolan-2-yl)(2S,4R,9R,10R)-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]dec-7-yl]methyl}-3-methylperhydro-2H-pyran-2-yl)propanoic acid
(2R)-2-[(2R,3S,6R)-6-[[(1R,3S,5R,6R,7R,9R)-3-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-tetrahydropyran-2-yl]-3-methyl-tetrahydrofuran-2-yl]-5-methyl-tetrahydrofuran-2-yl]-7-methoxy-1,3,6-trimethyl-4,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyl-tetrahydropyran-2-yl]propanoic acid
2H-Pyran-2-acetic acid, tetrahydro-6-[[(2S,4R,5R,7R,9R,10R)-9-methoxy-2,4,10-trimethyl-2-[(2S,2'R,3'S,5R,5'R)-octahydro-2,3'-dimethyl-5'-[(2S,3S,5R,6R)-tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl][2,2'-bifuran]-5-yl]-1,6-dioxaspiro[4.5]dec-7-yl]methyl]-.alpha.,3-dimethyl-, (.alpha.R,2R,3S,6R)-
Pubchem:
34230
Cas:
28380-24-7
Gnps:
CCMSLIB00005734310
Zinc:
ZINC000085552063
Kegg Ligand:
C11609
Chebi:
7569
Nmrshiftdb2:
60066633
Metabolights:
MTBLC7569
Chembl:
CHEMBL405862
Comptox:
DTXSID9041079
Drugbank:
DB14056
CPRiL:
986
SMILES: O1CCCCC1CC(O2)CCCC23CCC(O3)C4CCC(O4)C5CCC(O5)C6CCCCO6
Level: 4
Mol. Weight: 724.97 g/mol
SMILES: O1CCCCC1CC(O2)CCCC23CCC(O3)C4CCC(O4)C5CCCO5
Level: 3
Mol. Weight: 724.97 g/mol
SMILES: O1CCCCC12CCC(O2)C3CCC(O3)C4CCC(O4)C5CCCCO5
Level: 3
Mol. Weight: 724.97 g/mol
SMILES: O1CCCCC1CC(O2)CCCC23CCC(O3)C4CCCO4
Level: 2
Mol. Weight: 724.97 g/mol
SMILES: O1CCCCC12CCC(O2)C3CCC(O3)C4CCCO4
Level: 2
Mol. Weight: 724.97 g/mol
SMILES: O1CCCC1C2CCC(O2)C3CCCCO3
Level: 2
Mol. Weight: 724.97 g/mol
SMILES: O1CCCCC1CC(O2)CCCC23CCCO3
Level: 1
Mol. Weight: 724.97 g/mol
SMILES: O1CCCCC12CCC(O2)C3CCCO3
Level: 1
Mol. Weight: 724.97 g/mol
SMILES: O1CCCC1C2CCCCO2
Level: 1
Mol. Weight: 724.97 g/mol
SMILES: O1CCCC1C2CCCO2
Level: 1
Mol. Weight: 724.97 g/mol
SMILES: O1CCCC12CCCCO2
Level: 0
Mol. Weight: 724.97 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 724.97 g/mol
SMILES: C1CCOC1
Level: 0
Mol. Weight: 724.97 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.59
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -2.680
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 378.29
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.920
- Plasma Protein Binding
- 103.65
- 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
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 2.860
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -6.760
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.760
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.840
- 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
- Toxic
- T. Pyriformis
- -688402.940
- Rat (Acute)
- 4.000
- Rat (Chronic Oral)
- 2.000
- Fathead Minnow
- 875.630
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 75280.820
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 3.170
- Log(P)
- 5.8
- Log S
- -5.65
- Log(Vapor Pressure)
- -2389.1
- Melting Point
- 122.0
- pKa Acid
- 0.63
- pKa Basic
- 6.78
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7646 |
| Branched-chain-amino-acid aminotransferase, mitochondrial | O15382 | BCAT2_HUMAN | Homo sapiens | 3 | 0.7530 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7455 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7087 |