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535974-91-5,MFCD09971003
Catalog No.:AA00DLT7

535974-91-5 | Benzeneacetic acid, 4-hydroxy-3-iodo-5-methoxy-,[(2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-3a,3b,6,6a,9a,10,11,11a-octahydro-6a-hydroxy-8,10-dimethyl-11a-(1-methylethenyl)-7-oxo-2-(phenylmethyl)-7H-2,9b-epoxyazuleno[5,4-e]-1,3-benzodioxol-5-yl]methyl ester

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  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00DLT7
Chemical Name:
Benzeneacetic acid, 4-hydroxy-3-iodo-5-methoxy-,[(2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-3a,3b,6,6a,9a,10,11,11a-octahydro-6a-hydroxy-8,10-dimethyl-11a-(1-methylethenyl)-7-oxo-2-(phenylmethyl)-7H-2,9b-epoxyazuleno[5,4-e]-1,3-benzodioxol-5-yl]methyl ester
CAS Number:
535974-91-5
Molecular Formula:
C37H39IO9
Molecular Weight:
754.6046
MDL Number:
MFCD09971003
SMILES:
COc1cc(CC(=O)OCC2=C[C@H]3[C@H]4O[C@]5(O[C@]3([C@H]3[C@@](C2)(O)C(=O)C(=C3)C)[C@@H](C[C@@]4(O5)C(=C)C)C)Cc2ccccc2)cc(c1O)I
Properties
Computed Properties
 
Complexity:
1370  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
7  
Heavy Atom Count:
47  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
9  
Undefined Atom Stereocenter Count:
1  
XLogP3:
5.2  

Literature

Title: Resiniferatoxin induces death of bladder cancer cells associated with mitochondrial dysfunction and reduces tumor growth in a xenograft mouse model.

Journal: Chemico-biological interactions 20141205

Title: Capsaicin induces theta-band synchronization between gustatory and autonomic insular cortices.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20120926

Title: HCl-induced and ATP-dependent upregulation of TRPV1 receptor expression and cytokine production by human esophageal epithelial cells.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20120901

Title: Nucleotides control the excitability of sensory neurons via two P2Y receptors and a bifurcated signaling cascade.

Journal: Pain 20110801

Title: Inhibition of fatty acid amide hydrolase unmasks CB1 receptor and TRPV1 channel-mediated modulation of glutamatergic synaptic transmission in midbrain periaqueductal grey.

Journal: British journal of pharmacology 20110701

Title: Energetic metabolism and human sperm motility: impact of CB₁ receptor activation.

Journal: Endocrinology 20101201

Title: Stimulus-dependent requirement of ion channels for microglial NADPH oxidase-mediated production of reactive oxygen species.

Journal: Journal of neuroimmunology 20100825

Title: Chronic femoral artery occlusion augments exercise pressor reflex in decerebrated rats.

Journal: American journal of physiology. Heart and circulatory physiology 20100701

Title: Neuroprotection induced by vitamin E against oxidative stress in hippocampal neurons: involvement of TRPV1 channels.

Journal: Molecular nutrition & food research 20100401

Title: Reduction of bone cancer pain by CB1 activation and TRPV1 inhibition.

Journal: Journal of anesthesia 20100401

Title: Anandamide potentiation of miniature spontaneous excitatory synaptic transmission is mediated via IP3 pathway.

Journal: Neurochemistry international 20100301

Title: The role of transient receptor potential vanilloid-1 on neural responses to acids by the chorda tympani, glossopharyngeal and superior laryngeal nerves in mice.

Journal: Neuroscience 20100217

Title: Glycolic acid induces keratinocyte proliferation in a skin equivalent model via TRPV1 activation.

Journal: Journal of dermatological science 20100201

Title: Fas-associated factor 1 is a negative regulator in capsaicin induced cancer cell apoptosis.

Journal: Cancer letters 20100128

Title: Nerve growth factor enhances cough and airway obstruction via TrkA receptor- and TRPV1-dependent mechanisms.

Journal: Thorax 20090901

Title: Involvement of increased expression of transient receptor potential melastatin 8 in oxaliplatin-induced cold allodynia in mice.

Journal: Neuroscience letters 20090717

Title: HCl-activated neural and epithelial vanilloid receptors (TRPV1) in cat esophageal mucosa.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20090701

Title: Primary afferents with TRPM8 and TRPA1 profiles target distinct subpopulations of rat superficial dorsal horn neurones.

Journal: British journal of pharmacology 20090601

Title: TRPV1 channels control synaptic plasticity in the developing superior colliculus.

Journal: The Journal of physiology 20090601

Title: Functional interaction between TRPV1 and mu-opioid receptors in the descending antinociceptive pathway activates glutamate transmission and induces analgesia.

Journal: Journal of neurophysiology 20090501

Title: TRPV1: contribution to retinal ganglion cell apoptosis and increased intracellular Ca2+ with exposure to hydrostatic pressure.

Journal: Investigative ophthalmology & visual science 20090201

Title: Capsaicin, a component of red peppers, induces expression of androgen receptor via PI3K and MAPK pathways in prostate LNCaP cells.

Journal: FEBS letters 20090105

Title: Methanandamide activation of a novel current in mouse trigeminal ganglion sensory neurons in vitro.

Journal: Neuropharmacology 20080101

Title: Tonic endovanilloid facilitation of glutamate release in brainstem descending antinociceptive pathways.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20071212

Title: Bone cancer increases transient receptor potential vanilloid subfamily 1 expression within distinct subpopulations of dorsal root ganglion neurons.

Journal: Neuroscience 20070824

Title: Activation of recombinant human TRPV1 receptors expressed in SH-SY5Y human neuroblastoma cells increases [Ca(2+)](i), initiates neurotransmitter release and promotes delayed cell death.

Journal: Journal of neurochemistry 20070801

Title: Role of TRPV1 and intracellular Ca2+ in excitation of cardiac sensory neurons by bradykinin.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20070701

Title: Arvanil, anandamide and N-arachidonoyl-dopamine (NADA) inhibit emesis through cannabinoid CB1 and vanilloid TRPV1 receptors in the ferret.

Journal: The European journal of neuroscience 20070501

Title: The vanilloid receptor initiates and maintains colonic hypersensitivity induced by neonatal colon irritation in rats.

Journal: Gastroenterology 20070201

Title: TRPV1 receptor mediates glutamatergic synaptic input to dorsolateral periaqueductal gray (dl-PAG) neurons.

Journal: Journal of neurophysiology 20070101

Title: Transient receptor potential vanilloid subtype 1 mediates microglial cell death in vivo and in vitro via Ca2+-mediated mitochondrial damage and cytochrome c release.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20061001

Title: Functional mapping of the transient receptor potential vanilloid 1 intracellular binding site.

Journal: Molecular pharmacology 20060901

Title: Signaling mechanisms of down-regulation of voltage-activated Ca2+ channels by transient receptor potential vanilloid type 1 stimulation with olvanil in primary sensory neurons.

Journal: Neuroscience 20060811

Title: Lack of evidence for functional TRPV1 vanilloid receptors in rat hippocampal nerve terminals.

Journal: Neuroscience letters 20060731

Title: Tactile allodynia initiated by local subcutaneous endothelin-1 is prolonged by activation of TRPV-1 receptors.

Journal: Experimental biology and medicine (Maywood, N.J.) 20060601

Title: Participation of the spinal TRPV1 receptors in formalin-evoked pain transduction: a study using a selective TRPV1 antagonist, iodo-resiniferatoxin.

Journal: The Journal of pharmacy and pharmacology 20060401

Title: Effect of olvanil and anandamide on vagal C-fiber subtypes in guinea pig lung.

Journal: British journal of pharmacology 20051001

Title: 5-Iodoresiniferatoxin evokes hypothermia in mice and is a partial transient receptor potential vanilloid 1 agonist in vitro.

Journal: The Journal of pharmacology and experimental therapeutics 20050901

Title: The taming of capsaicin. Reversal of the vanilloid activity of N-acylvanillamines by aromatic iodination.

Journal: Journal of medicinal chemistry 20050714

Title: Inhibition of peripheral vanilloid TRPV1 receptors reduces noxious heat-evoked responses of dorsal horn neurons in naïve, carrageenan-inflamed and neuropathic rats.

Journal: The European journal of neuroscience 20050701

Title: TRPV1 regulators mediate gentamicin penetration of cultured kidney cells.

Journal: Hearing research 20050601

Title: Extracellular cations sensitize and gate capsaicin receptor TRPV1 modulating pain signaling.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20050525

Title: Transient receptor potential vanilloid type 1 activation down-regulates voltage-gated calcium channels through calcium-dependent calcineurin in sensory neurons.

Journal: The Journal of biological chemistry 20050506

Title: Cloning and functional characterization of dog transient receptor potential vanilloid receptor-1 (TRPV1).

Journal: European journal of pharmacology 20050418

Title: VR-1 receptor blockade attenuates the pressor response to capsaicin but has no effect on the pressor response to contraction in cats.

Journal: American journal of physiology. Heart and circulatory physiology 20050401

Title: Pharmacological investigation of hydrogen sulfide (H2S) contractile activity in rat detrusor muscle.

Journal: European journal of pharmacology 20050221

Title: Cloning and pharmacological characterization of mouse TRPV1.

Journal: Neuroscience letters 20041103

Title: Sensing tissue ischemia: another new function for capsaicin receptors?

Journal: Circulation 20040928

Title: VR1 receptor activation induces glutamate release and postsynaptic firing in the paraventricular nucleus.

Journal: Journal of neurophysiology 20040901

Title: TRPV1 and cough.

Journal: Thorax 20040901

Title: Antitussive activity of iodo-resiniferatoxin in guinea pigs.

Journal: Thorax 20040901

Title: Effects of TRPV1 receptor antagonists on stimulated iCGRP release from isolated skin of rats and TRPV1 mutant mice.

Journal: Pain 20040601

Title: Lack of role for the vanilloid receptor in response to several inspired irritant air pollutants in the C57Bl/6J mouse.

Journal: Neuroscience letters 20040520

Title: Modulation of trigeminal sensory neuron activity by the dual cannabinoid-vanilloid agonists anandamide, N-arachidonoyl-dopamine and arachidonyl-2-chloroethylamide.

Journal: British journal of pharmacology 20040401

Title: Resiniferatoxin binds to the capsaicin receptor (TRPV1) near the extracellular side of the S4 transmembrane domain.

Journal: Biochemistry 20040309

Title: Activation of peripheral cannabinoid CB1 receptors inhibits mechanically evoked responses of spinal neurons in noninflamed rats and rats with hindpaw inflammation.

Journal: The European journal of neuroscience 20031001

Title: N-oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia.

Journal: The Journal of biological chemistry 20030418

Title: Presynaptic facilitation of glutamatergic synapses to dopaminergic neurons of the rat substantia nigra by endogenous stimulation of vanilloid receptors.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20030415

Title: The actions of anandamide on rat superficial medullary dorsal horn neurons in vitro.

Journal: The Journal of physiology 20030401

Title: Neurogenic responses mediated by vanilloid receptor-1 (TRPV1) are blocked by the high affinity antagonist, iodo-resiniferatoxin.

Journal: British journal of pharmacology 20030301

Title: Functional properties of the high-affinity TRPV1 (VR1) vanilloid receptor antagonist (4-hydroxy-5-iodo-3-methoxyphenylacetate ester) iodo-resiniferatoxin.

Journal: The Journal of pharmacology and experimental therapeutics 20021201

Title: Characterization of the vanilloid receptor 1 antagonist iodo-resiniferatoxin on the afferent and efferent function of vagal sensory C-fibers.

Journal: The Journal of pharmacology and experimental therapeutics 20021101

Title: Capsaicin activation of glutamatergic synaptic transmission in the rat locus coeruleus in vitro.

Journal: The Journal of physiology 20020901

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Tags:535974-91-5 Molecular Formula|535974-91-5 MDL|535974-91-5 SMILES|535974-91-5 Benzeneacetic acid, 4-hydroxy-3-iodo-5-methoxy-,[(2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-3a,3b,6,6a,9a,10,11,11a-octahydro-6a-hydroxy-8,10-dimethyl-11a-(1-methylethenyl)-7-oxo-2-(phenylmethyl)-7H-2,9b-epoxyazuleno[5,4-e]-1,3-benzodioxol-5-yl]methyl ester