Nigericin

Details

• Internal ID: ba81092d-8ebe-4539-8ce0-a2382b8fd000
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Ethers > Acetals > Ketals
• IUPAC Name: (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
• SMILES (Canonical): CC1CCC(OC1C(C)C(=O)O)CC2CC(C(C3(O2)C(CC(O3)(C)C4CCC(O4)(C)C5C(CC(O5)C6C(CC(C(O6)(CO)O)C)C)C)C)C)OC
• SMILES (Isomeric): C[C@H]1CC[C@@H](O[C@H]1[C@@H](C)C(=O)O)C[C@@H]2C[C@H]([C@H]([C@@]3(O2)[C@@H](C[C@@](O3)(C)[C@H]4CC[C@@](O4)(C)[C@H]5[C@H](C[C@@H](O5)[C@@H]6[C@H](C[C@H]([C@@](O6)(CO)O)C)C)C)C)C)OC
• 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
• InChI Key: DANUORFCFTYTSZ-SJSJOXFOSA-N
• Popularity: 1,537 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₈O₁₁
• Molecular Weight: 725.00 g/mol
• Exact Mass: 724.47616298 g/mol
• Topological Polar Surface Area (TPSA): 142.00 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 5.71
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 9

Synonyms

• Azalomycin M
• Helixin C
• 28380-24-7
• Antibiotic K 178
• Antibiotic X-464
• RRU6GY95IS
• CHEBI:7569
• (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
• Helix C
• UNII-RRU6GY95IS
• BRN 1696755
• NSC292567
• X-464
• NIGERICIN [MI]
• 28643-80-3
• BSPBio_001599
• SCHEMBL149611
• CHEMBL405862
• DTXSID9041079
• HMS1791P21
• HMS1989P21
• HMS3402P21
• Antibiotic K178;Antibiotic X464
• CA-421
• AKOS040742303
• DB14056
• NCGC00163412-02
• HY-127019
• CS-0091495
• 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
• (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
• 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)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7526	75.26%
Caco-2	-	0.8688	86.88%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8112	81.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8711	87.11%
OATP1B3 inhibitior	+	0.9214	92.14%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4905	49.05%
P-glycoprotein inhibitior	+	0.8023	80.23%
P-glycoprotein substrate	-	0.7714	77.14%
CYP3A4 substrate	+	0.7250	72.50%
CYP2C9 substrate	-	0.5837	58.37%
CYP2D6 substrate	-	0.8808	88.08%
CYP3A4 inhibition	-	0.8685	86.85%
CYP2C9 inhibition	-	0.8840	88.40%
CYP2C19 inhibition	-	0.9262	92.62%
CYP2D6 inhibition	-	0.9579	95.79%
CYP1A2 inhibition	-	0.9178	91.78%
CYP2C8 inhibition	+	0.6370	63.70%
CYP inhibitory promiscuity	-	0.9702	97.02%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6406	64.06%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9126	91.26%
Skin irritation	-	0.6548	65.48%
Skin corrosion	-	0.9499	94.99%
Ames mutagenesis	-	0.5554	55.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6590	65.90%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.5552	55.52%
skin sensitisation	-	0.9323	93.23%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.5732	57.32%
Acute Oral Toxicity (c)	II	0.5606	56.06%
Estrogen receptor binding	+	0.6542	65.42%
Androgen receptor binding	+	0.7404	74.04%
Thyroid receptor binding	-	0.6165	61.65%
Glucocorticoid receptor binding	+	0.7187	71.87%
Aromatase binding	+	0.6960	69.60%
PPAR gamma	+	0.6997	69.97%
Honey bee toxicity	-	0.7699	76.99%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8013	80.13%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.94%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.84%	85.14%
CHEMBL220	P22303	Acetylcholinesterase	95.84%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	94.58%	96.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	93.82%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.17%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.51%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.18%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.14%	94.45%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.01%	96.47%
CHEMBL2581	P07339	Cathepsin D	88.91%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	88.71%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	88.33%	90.17%
CHEMBL2083	P15090	Fatty acid binding protein adipocyte	87.74%	95.71%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.50%	96.38%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.37%	96.77%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.40%	89.05%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.33%	91.11%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.19%	93.56%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.15%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.40%	96.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.77%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.86%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.59%	92.62%
CHEMBL3820	P35557	Hexokinase type IV	80.18%	91.96%

Plants that contains it

• Anisodus luridus
• Brugmansia arborea
• Datura innoxia
• Datura metel
• Datura stramonium
• Duboisia hopwoodii
• Duboisia leichhardtii
• Hyoscyamus albus
• Hyoscyamus muticus
• Hyoscyamus pusillus
• Hyoscyamus reticulatus
• Mandragora officinarum
• Scopolia carniolica
• Scopolia japonica
• Solandra grandiflora

Cross-Links

• PubChem: 34230
• LOTUS: LTS0039980
• wikiData: Q413762