resiniferatoxin (CHEBI:8809)

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CHEBI:8809 - resiniferatoxin

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ChEBI Name	resiniferatoxin

ChEBI ID	CHEBI:8809

Definition	A heteropentacyclic compound found in Euphorbia poissonii with molecular formula C₃₇H₄₀O₉. It is an agonist of the transient receptor potential cation channel subfamily V member 1 (TrpV1).

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB9454820, eMolecules:530768, Selleckchem:pmsf-phenylmethylsulfonyl-fluoride, ZINC000008220691

Download	Molfile XML SDF

more structures >>

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6EU - Ideal conformer

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M END): 20 ms

reading 86 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

86 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Molfile expand

Wikipedia	License
In biochemistry, phenylmethylsulfonyl fluoride (PMSF) is a serine protease inhibitor (serine hydrolase inactivator) commonly used in the preparation of cell lysates. PMSF does not inactivate all serine proteases. The effective concentration of PMSF is between 0.1 - 1 mM. The half-life is short in aqueous solutions (110 min at pH 7, 55 min at pH 7.5, and 35 min at pH 8, all at 25 °C). At 4˚C, pH 8, PMSF is almost completely degraded after 1 day. Stock solutions are usually made up in anhydrous ethanol, isopropanol, or corn oil and diluted immediately before use. PMSF reacts specifically with the active site serine residue in serine hydrolases. It does not bind to any other serine residues in the protein. This is a result of the hyperactivity of that serine residue caused by the specific environmental conditions in the enzyme's active site (catalytic triad). Because PMSF bonds covalently to the enzyme, the complex can be viewed by X-ray crystallography; it can therefore be used as a chemical label to identify an essential active site serine in an enzyme. Enzyme(active)Ser-O-H + F-SO2CH2C6H5 → EnzymeSer-O-SO2CH2C6H5 + HF Serine protease + PMSF → Irreversible enzyme-PMS complex + HF The median lethal dose between 150–215 mg/kg (acetylcholine esterase inactivator). PMSF should be handled only inside a fume hood and while wearing gloves. DMSO is sometimes recommended as solvent for stock solutions, but should not be used as it makes intact skin permeable to PMSF.
Read full article at Wikipedia

Formula

C37H40O9

Net Charge

Average Mass

628.718

Monoisotopic Mass

628.26723

InChI

InChI=1S/C37H40O9/c1-21(2)35-17-23(4)37-27(33(35)44-36(45-35,46-37)19-24-9-7-6-8-10-24)14-26(18-34(41)30(37)13-22(3)32(34)40)20-43-31(39)16-25-11-12-28(38)29(15-25)42-5/h6-15,23,27,30,33,38,41H,1,16-20H2,2-5H3/t23-,27+,30-,33-,34-,35-,36-,37-/m1/s1

InChIKey

DSDNAKHZNJAGHN-MXTYGGKSSA-N

SMILES

C=1(C=C(C(=CC1)O)OC)CC(OCC2=C[C@@]3([C@]4([C@]5([C@](C2)(C(=O)C(=C5)C)O)[H])O[C@]6(O[C@@]([C@@]3(O6)[H])(C(=C)C)C[C@H]4C)CC=7C=CC=CC7)[H])=O

Metabolite of Species	Details
Euphorbia poissonii (NCBI:txid212962)	See: Book: Harborne, Phytochemical Dictionary Second Edition, Taylor and Francis (1999), Chapter 52.
Euphorbia resinifera (NCBI:txid457265)	See: Book: Harborne, Phytochemical Dictionary Second Edition, Taylor and Francis (1999), Chapter 52.

Roles Classification
Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. neurotoxin A poison that interferes with the functions of the nervous system. analgesic An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. TRPV1 agonist An agonist at the transient receptor potential vanilloid 1 (TRPV1).

Application(s):	analgesic An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	resiniferatoxin (CHEBI:8809) has role analgesic (CHEBI:35480) resiniferatoxin (CHEBI:8809) has role neurotoxin (CHEBI:50910) resiniferatoxin (CHEBI:8809) has role plant metabolite (CHEBI:76924) resiniferatoxin (CHEBI:8809) has role TRPV1 agonist (CHEBI:140535) resiniferatoxin (CHEBI:8809) is a carboxylic ester (CHEBI:33308) resiniferatoxin (CHEBI:8809) is a diterpenoid (CHEBI:23849) resiniferatoxin (CHEBI:8809) is a enone (CHEBI:51689) resiniferatoxin (CHEBI:8809) is a monomethoxybenzene (CHEBI:25235) resiniferatoxin (CHEBI:8809) is a organic heteropentacyclic compound (CHEBI:38164) resiniferatoxin (CHEBI:8809) is a ortho ester (CHEBI:71989) resiniferatoxin (CHEBI:8809) is a phenols (CHEBI:33853) resiniferatoxin (CHEBI:8809) is a tertiary α-hydroxy ketone (CHEBI:139592)

IUPAC Name

[(2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-2-benzyl-6a-hydroxy-8,10-dimethyl-7-oxo-11a-(prop-1-en-2-yl)-3a,6,6a,7,9a,10,11,11a-octahydro-3bH-2,9b-epoxyazuleno[4',5':5,6]benzo[1,2-d][1,3]dioxol-5-yl]methyl (4-hydroxy-3-methoxyphenyl)acetate

Synonyms	Sources
(+)-resiniferatoxin	ChEBI
resiniferatoxin	KEGG COMPOUND
resiniferatoxin	UniProt
RTX	ChemIDplus

Manual Xrefs	Databases
6EU	PDBeChem
C00003478	KNApSAcK
C09179	KEGG COMPOUND
DB06515	DrugBank
Resiniferatoxin	Wikipedia
View more database links

Registry Numbers	Types	Sources
5371150	Reaxys Registry Number	Reaxys
57444-62-9	CAS Registry Number	ChemIDplus

Citations	Types	Sources
26779292	PubMed citation	Europe PMC
27281200	PubMed citation	Europe PMC
2747924	PubMed citation	Europe PMC
27529257	PubMed citation	Europe PMC
29041773	PubMed citation	Europe PMC
29271803	PubMed citation	Europe PMC
29320813	PubMed citation	Europe PMC
29361418	PubMed citation	Europe PMC
29672450	PubMed citation	Europe PMC
29728656	PubMed citation	Europe PMC
30015705	PubMed citation	Europe PMC
30399572	PubMed citation	Europe PMC
30590777	PubMed citation	Europe PMC
31090543	PubMed citation	Europe PMC
31124075	PubMed citation	Europe PMC
31180583	PubMed citation	Europe PMC
31503071	PubMed citation	Europe PMC
31811858	PubMed citation	Europe PMC
32064609	PubMed citation	Europe PMC
32292906	PubMed citation	Europe PMC
7189445	PubMed citation	Europe PMC

Last Modified

02 September 2021

CHEBI:8809 - resiniferatoxin

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