Exact Mass: 263.1341486
Exact Mass Matches: 263.1341486
Found 500 metabolites which its exact mass value is equals to given mass value 263.1341486
,
within given mass tolerance error 0.05 dalton. Try search metabolite list with more accurate mass tolerance error
0.01 dalton.
Nortriptyline
Nortriptyline is an organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(methylamino)propylidene group at position 5. It is an active metabolite of amitriptyline. It has a role as a drug metabolite, an antidepressant, an adrenergic uptake inhibitor, an analgesic, an antineoplastic agent and an apoptosis inducer. It is an organic tricyclic compound and a secondary amine. It is functionally related to an amitriptyline. It derives from a hydride of a dibenzo[a,d][7]annulene. Nortriptyline hydrochloride, the active metabolite of [amitriptyline], is a tricyclic antidepressant (TCA). It is used in the treatment of major depression and is also used off-label for chronic pain and other conditions. Nortriptyline is a Tricyclic Antidepressant. Nortriptyline is a tricyclic antidepressant that is also used in smoking cessation. Nortriptyline can cause mild and transient serum enzyme elevations and is rare cause of clinically apparent acute and chronic cholestatic liver injury. Nortriptyline is a natural product found in Senegalia berlandieri with data available. Nortriptyline is a tricyclic antidepressant agent used for short-term treatment of various forms of depression. Nortriptyline blocks the norepinephrine presynaptic receptors, thereby blocking the reuptake of this neurotransmitter and raising the concentration in the synaptic cleft in the CNS. Nortriptyline also binds to alpha-adrenergic, histaminergic and cholinergic receptors. Long-term treatment with nortriptyline produces a downregulation of adrenergic receptors due to the increased stimulation of these receptors. Nortriptyline hydrochloride, the N-demethylated active metabolite of amitriptyline, is a dibenzocycloheptene-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, nortriptyline does not affect mood or arousal, but may cause sedation. In depressed individuals, nortriptyline exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Secondary amine TCAs, such as nortriptyline, are more potent inhibitors of norepinephrine reuptake than tertiary amine TCAs, such as amitriptyline. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine-H1 receptors, α1-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Nortriptyline exerts less anticholinergic and sedative side effects compared to the tertiary amine TCAs, amitriptyline and clomipramine. Nortriptyline may be used to treat depression, chronic pain (unlabeled use), irritable bowel syndrome (unlabeled use), diabetic neuropathy (unlabeled use), post-traumatic stress disorder (unlabeled use), and for migraine prophylaxis (unlabeled use). A metabolite of AMITRIPTYLINE that is also used as an antidepressive agent. Nortriptyline is used in major depression, dysthymia, and atypical depressions. See also: Nortriptyline Hydrochloride (active moiety of). Nortriptyline hydrochloride, the N-demethylated active metabolite of amitriptyline, is a dibenzocycloheptene-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, nortriptyline does not affect mood or arousal, but may cause sedation. In depressed individuals, nortriptyline exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Secondary amine TCAs, such as nortriptyline, are more potent inhibitors of norepinephrine reuptake than tertiary amine TCAs, such as amitriptyline. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine-H1 receptors, α1-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Nortriptyline exerts less anticholinergic and sedative side effects compared to the tertiary amine TCAs, amitriptyline and clomipramine. Nortriptyline may be used to treat depression, chronic pain (unlabeled use), irritable bowel syndrome (unlabeled use), diabetic neuropathy (unlabeled use), post-traumatic stress disorder (unlabeled use), and for migraine prophylaxis (unlabeled use). An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(methylamino)propylidene group at position 5. It is an active metabolite of amitriptyline. N - Nervous system > N06 - Psychoanaleptics > N06A - Antidepressants > N06AA - Non-selective monoamine reuptake inhibitors D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors C78272 - Agent Affecting Nervous System > C265 - Antidepressant Agent > C94727 - Tricyclic Antidepressant D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents D049990 - Membrane Transport Modulators CONFIDENCE standard compound; EAWAG_UCHEM_ID 3692 Nortriptyline (Desmethylamitriptyline), the main active metabolite of Amitriptyline, is a tricyclic antidepressant. Nortriptyline is a potent autophagy inhibitor and has anticancer effects[1][2][3]. N
Protriptyline
Protriptyline hydrochloride is a dibenzocycloheptene-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, protriptyline does not affect mood or arousal, but may cause sedation. In depressed individuals, protriptyline exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. In addition, TCAs down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine H1 receptors, α1-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Protriptyline may be used for the treatment of depression. N - Nervous system > N06 - Psychoanaleptics > N06A - Antidepressants > N06AA - Non-selective monoamine reuptake inhibitors D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors C78272 - Agent Affecting Nervous System > C265 - Antidepressant Agent > C94727 - Tricyclic Antidepressant D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents D049990 - Membrane Transport Modulators
2-Ethyl-5-methyl-3,3-diphenyl-1-pyrroline
2-Ethyl-5-methyl-3,3-diphenyl-1-pyrroline is a metabolite of methadone. Methadone (also known as Symoron, Dolophine, Amidone, Methadose, Physeptone, Heptadon, Phy and many other names) is a synthetic opioid, used medically as an analgesic and a maintenance anti-addictive for use in patients with opioid dependency. It was developed in Germany in 1937. Although chemically unlike morphine or heroin, methadone acts on the same opioid receptors as these drugs, and thus has many of the same effects. (Wikipedia)
4-O-(beta-L-Araf)-cis-L-Hyp
An O(4)-glycosyl-L-hydroxyproline that is cis-L-hydroxylproline glycosylated by a beta-L-Araf moiety.
Girinimbine
Girinimbine is a member of carbazoles. It has a role as a metabolite. Girinimbine is a natural product found in Clausena vestita, Murraya euchrestifolia, and other organisms with data available. Girinimbine is found in herbs and spices. Girinimbine is an alkaloid from the roots of Murraya koenigii (curry leaf tree A natural product found in Clausena harmandiana.
(E,E)-Lansamide I
(E,E)-Lansamide I is found in fruits. (E,E)-Lansamide I is an alkaloid from the leaves and seeds of Clausena lansium (wampee
Dehydroanonaine
Dehydroanonaine is found in coffee and coffee products. Dehydroanonaine is an alkaloid from the leaves of Nelumbo nucifera (East India lotus
Methionyl-Asparagine
Methionyl-Asparagine is a dipeptide composed of methionine and asparagine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.
Asparaginyl-Methionine
Asparaginyl-Methionine is a dipeptide composed of asparagine and methionine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.
Hydroxyvalerylcarnitine
Hydroxyvalerylcarnitine is an acylcarnitine. More specifically, it is an hydroxyvaleric acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review [Dambrova et al. 2021, Physiological Reviews], acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. Hydroxyvalerylcarnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine hydroxyvalerylcarnitine is a member of the most abundant group of carnitines in the body, comprising more than 50\\% of all acylcarnitines quantified in tissues and biofluids (PMID: 31920980). Some short-chain carnitines have been studied as supplements or treatments for a number of diseases, including neurological disorders and inborn errors of metabolism. In particular hydroxyvalerylcarnitine is elevated in the blood or plasma of individuals with 3-hydroxy-3-methylglutaryl-coenzyme A lyase deficiency (PMID: 28583327) and holocarboxylase synthetase deficiency (PMID: 27114915). It is also decreased in the blood or plasma of individuals with psoriasis (PMID: 33391503). Carnitine acetyltransferase (CrAT, EC:2.3.1.7) is responsible for the synthesis of all short-chain and short branched-chain acylcarnitines (PMID: 23485643). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available at [Dambrova et al. 2021, Physiological Reviews].
N-(Heptan-4-yl)benzo[d][1,3]dioxole-5-carboxamide
N-(Heptan-4-yl)benzo[d][1,3]dioxole-5-carboxamide is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]")
Lansiumamide B
Lansiumamide B is found in fruits. Lansiumamide B is isolated from seeds of Clausena lansium (wampee). Isolated from seeds of Clausena lansium (wampee). Lansiumamide B is found in fruits.
2-Naphthalenol 2-aminobenzoate
2-Naphthalenol 2-aminobenzoate is a flavouring ingredient for beverages, baked goods and candies. Flavouring ingredient for beverages, baked goods and candies
demethylmaprotiline
demethylmaprotiline is a metabolite of maprotiline. Maprotiline (sold as Deprilept, Ludiomil, Psymion) is a tetracyclic antidepressant (TeCA). However, Maprotilines fourth ring is spurious, as formed by a bridge across the central tricyclic ring. It is a strong norepinephrine reuptake inhibitor with only weak effects on serotonin and dopamine reuptake. (Wikipedia)
desethylzaleplon
desethylzaleplon is a metabolite of zaleplon. Zaleplon (marketed under the brand names Sonata and Starnoc) is a sedative/hypnotic, mainly used for insomnia. It is a nonbenzodiazepine hypnotic from the pyrazolopyrimidine class. In terms of adverse effects zaleplon appears to offer little improvement compared to both benzodiazepines and other non-benzodiazepine Z-drugs. Sonata (US) is manufactured by King Pharm. of Bristol, TN; Starnoc has been discontinued in Canada. (Wikipedia)
Creatine riboside
Creatine riboside is a conjugate between creatine and ribose. It is a novel diagnostic marker for lung cancer that is elevated in the urine of non-small cell lung cancer subjects (PMID: 24736543). Creatine riboside may be a product of both high creatine levels within tumor cells and the characteristic high phosphate flux of cancer cells. Increased mutagenicity of creatine and ribose pyrolysis products in cooked foods has been reported, suggesting a functional role of creatine riboside in tumorigenesis (PMID: 24736543). Creatine riboside is likely not an enzyme-synthesized product as it can be formed spontaneously by mixing creatine with ribose. It can be synthesized in modestly high yields by reacting ribose and creatine in the presence of ammonium bicarbonate and heating the two compounds at 80°C for 10 minutes.
Melperone
D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014150 - Antipsychotic Agents D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents N - Nervous system > N05 - Psycholeptics > N05A - Antipsychotics > N05AD - Butyrophenone derivatives D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants C78272 - Agent Affecting Nervous System > C29710 - Antipsychotic Agent
N(6)-L-Homocysteinyl-L-lysine
C10H21N3O3S (263.13035560000003)
Olaquindox
C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent
Tiflorex
C78272 - Agent Affecting Nervous System > C29728 - Anorexiant
5-Amino-2-[(2-amino-3-carboxypropanoyl)oxyamino]pentanoic acid
2-cis-abscisate
2-cis-abscisate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 2-cis-abscisate can be found in a number of food items such as common wheat, lemon thyme, black raspberry, and acorn, which makes 2-cis-abscisate a potential biomarker for the consumption of these food products.
Bayonox
C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent Olaquindox [BAN:INN] is a quinoxaline derivative.
Axisothiocyanate 1
Epipolasin A
3,7-Dihydro-3,3,10-trimethylpyrano[2,3-c]carbazole
Dehydroanonaine
Dioxypyramidon
C13H17N3O3 (263.12698520000004)
CONFIDENCE standard compound; EAWAG_UCHEM_ID 2708
MELPERONE
D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014150 - Antipsychotic Agents D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents N - Nervous system > N05 - Psycholeptics > N05A - Antipsychotics > N05AD - Butyrophenone derivatives D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants C78272 - Agent Affecting Nervous System > C29710 - Antipsychotic Agent
11-isothiocyano-7beta-H-eudesm-5-ene|11-isothiocyano-7betaH-eudesm-5-ene
(S)-8-acetyl-4-methoxy-9-methyl-6,7,8,9-tetrahydro-[1,3]dioxolo[4,5-h]isoquinoline|N-acetyl-anhalonine|N-Acetylanhalomine
C14H17NO4 (263.11575220000003)
Me glycoside,Me ester,N-Ac-alpha-D-Pyranose-4-Amino-4-deoxyglucuronic acid
2-Decene-6,8-diynoic acid, 9CI-2-Phenylethenylamide,(Z-)|dec-1c-en-6,8-diinsaeure-cis-styrylamid
rel-(1S,3aS,4S,8aR)-4-isothiocyanato-3a,7-dimethyl-1,2,3,3a,4,5,6,8a-octahydro-1-(prop-2-yl)azulene|rel-4,5-epi-10-isothiocyanatoisodauc-6-ene
4alpha-isothiocyanatogorgon-11-ene|4alpha-isothiocyanogorgon-11-ene
(1R*,2R*,3R*,5R*,6S*,7S*)-2-Thiocyanatopupukeanane
1-methyl-4-(1-methyl-2,5-dihydro-pyrrol-2-yl)-9H-beta-carboline|Dehydrobrevicollin
1-ethyl-5-(7-hydroxy-benzo[1,3]dioxol-5-yl)-piperidin-2-one|Campedin|campedine
C14H17NO4 (263.11575220000003)
6-deoxy-6-C-(2,5-dihydroxyhexyl)-2(R),5(R)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine
10-isothiocyanato-11-axene|7-Isothiocyanato-11-oppositene
2,8-Decadiene-4,6-diynoic acid-2-Phenylethuylamide
(S)-2-(2-(2-Aminoacetamido)-4-(methylthio)butanamido)acetic acid
Nortriptyline
N - Nervous system > N06 - Psychoanaleptics > N06A - Antidepressants > N06AA - Non-selective monoamine reuptake inhibitors D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors C78272 - Agent Affecting Nervous System > C265 - Antidepressant Agent > C94727 - Tricyclic Antidepressant D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents CONFIDENCE standard compound; INTERNAL_ID 1567 D049990 - Membrane Transport Modulators Nortriptyline (Desmethylamitriptyline), the main active metabolite of Amitriptyline, is a tricyclic antidepressant. Nortriptyline is a potent autophagy inhibitor and has anticancer effects[1][2][3]. N
Dioxypyramidon
C13H17N3O3 (263.12698520000004)
CONFIDENCE standard compound; EAWAG_UCHEM_ID 2708
3,3,5-trimethyl-11H-pyrano[3,2-a]carbazole
Melperon
D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014150 - Antipsychotic Agents D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents N - Nervous system > N05 - Psycholeptics > N05A - Antipsychotics > N05AD - Butyrophenone derivatives D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants C78272 - Agent Affecting Nervous System > C29710 - Antipsychotic Agent CONFIDENCE standard compound; INTERNAL_ID 2513 CONFIDENCE standard compound; INTERNAL_ID 8494
(4S,5Z,6S)-4-(2-methoxy-2-oxoethyl)-5-[2-[(E)-3-phenylprop-2-enoyl]oxyethylidene]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylic acid
protriptyline
N - Nervous system > N06 - Psychoanaleptics > N06A - Antidepressants > N06AA - Non-selective monoamine reuptake inhibitors D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors C78272 - Agent Affecting Nervous System > C265 - Antidepressant Agent > C94727 - Tricyclic Antidepressant D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents D049990 - Membrane Transport Modulators
beta-naphthyl anthranilate
CONFIDENCE standard compound; INTERNAL_ID 690; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9953; ORIGINAL_PRECURSOR_SCAN_NO 9951 CONFIDENCE standard compound; INTERNAL_ID 690; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9983; ORIGINAL_PRECURSOR_SCAN_NO 9981 CONFIDENCE standard compound; INTERNAL_ID 690; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10003; ORIGINAL_PRECURSOR_SCAN_NO 10001 CONFIDENCE standard compound; INTERNAL_ID 690; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10052; ORIGINAL_PRECURSOR_SCAN_NO 10050 CONFIDENCE standard compound; INTERNAL_ID 690; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10052; ORIGINAL_PRECURSOR_SCAN_NO 10051
girinimbin
1H-Indole-3-carboxaldehyde,2-methyl-1-[(3-methylphenyl)methyl]-(9CI)
1H-Indole-3-carboxaldehyde,2-methyl-1-[(4-methylphenyl)methyl]-(9CI)
(2R,3S)-3-(tert-Butoxycarbonyl)aMino-1,2-epoxy-4-phenylbutane
2-(2,2-Diethoxyethyl)-1H-isoindole-1,3(2H)-dione
C14H17NO4 (263.11575220000003)
(5-Methyl-pyridin-2-yl)-piperidin-4-yl-amine dihydrochloride
C11H19Cl2N3 (263.09559540000004)
N1-(1-ISOPROPYL-2-METHYLPROPYL)-2-BROMO-2-METHYLPROPANAMIDE
1H-Indole-3-carboxaldehyde,7-ethyl-1-(phenylmethyl)-(9CI)
1-(4-ISOPROPOXY-PHENYL)-5-OXO-PYRROLIDINE-3-CARBOXYLIC ACID
C14H17NO4 (263.11575220000003)
ethyl 1-[4-(hydroxymethyl)phenyl]piperidine-4-carboxylate
4-HYDROXY-2,5-DIMETHYL-3-(MORPHOLINOMETHYL)-6-OXO-1,3-CYCLOHEXADIENE-1-CARBONITRILE
C13H17N3O3 (263.12698520000004)
N-Cbz- Piperidine-3-carboxylic acid
C14H17NO4 (263.11575220000003)
2-Isoproxypyridine-4-boronic acid pinacol ester
C14H22BNO3 (263.16926520000004)
Hydroxypethidine
C78272 - Agent Affecting Nervous System > C67413 - Opioid Receptor Agonist
1-Benzylpyrrolidine-3,4-dicarboxylic acid monomethyl ester
C14H17NO4 (263.11575220000003)
2-Isopropoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine
C14H22BNO3 (263.16926520000004)
2-(2-formylphenoxy)-N-(oxolan-2-ylmethyl)acetamide
C14H17NO4 (263.11575220000003)
TERT-BUTYL ((S)-1-((S)-OXIRAN-2-YL)-2-PHENYLETHYL)CARBAMATE
(s)-piperidine-1,3-dicarboxylic acid 1-benzyl ester
C14H17NO4 (263.11575220000003)
8-N-BOC-5,6,7,8-TETRAHYDRO-1,8-NAPHTHYRIDIN-2-METHYLAMINE
METHYL 6-HYDROXY-7-(1-METHYLALLYL)-5-OXO-1,2,3,5-TETRAHYDROINDOLIZINE-8-CARBOXYLATE
C14H17NO4 (263.11575220000003)
3-Dimethylamino-1-(naphthalen-1-yl)propan-1-one hydrochloride
8-Amino-4-Boc-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine
2-(6-Methylpyridin-2-yl)-1-(quinoxalin-6-yl)ethanone
(S)-1-Benzyl 3-Methyl pyrrolidine-1,3-dicarboxylate
C14H17NO4 (263.11575220000003)
Methyl 1-(4-methoxybenzyl)-5-oxo-3-pyrrolidinecarboxylate
C14H17NO4 (263.11575220000003)
1,3-dimethyl-5-[2-(1-methylpyrrolidin-2-ylidene)ethylidene]-1,3-diazinane-2,4,6-trione
C13H17N3O3 (263.12698520000004)
tert-butyl N-[(1S,2R)-1-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate
4,4,5,5-tetramethyl-2-(2-methyl-4-nitrophenyl)-1,3,2-dioxaborolane
1-BENZYL 2-METHYL 2-METHYLPYRROLIDINE-1,2-DICARBOXYLATE
C14H17NO4 (263.11575220000003)
(8-benzyl-1,4-dioxa-8-azaspiro[4.5]decan-6-yl)methanol
3,4,5-trimethoxy-2-(methoxymethyl)cinnamonitrile
C14H17NO4 (263.11575220000003)
6-((tert-Butyldimethylsilyloxy)methyl)furo[3,2-b]pyridine
TRANS-4-(1,1-DIMETHYLETHYLSULFONAMIDO)CYCLOHEXANECARBOXYLIC ACID
tert-butyl 1-(hydroxymethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate
1-N-ALLYL-3-PHENYL-2,3,4,5-TERAHYDRO-BENZO(D)AZEPINE
2-Methyl-2-propanyl (3R,4S)-3-hydroxy-4-phenyl-1-pyrrolidinecarbo xylate
1-PIPERAZINECARBOXYLIC ACID, 4-(2-PYRIDINYL)-, 1,1-DIMETHYLETHYL ESTER
4-BENZYLOXY-3-AMINO-A-[-BENZYL-N-(1-METHYL-2P-METHOXY PHENYL ETHER) AMINO-METHYL BENZYL ALCOHOL
5-AMINO-3-OXO-2,3-DIHYDRO-1H-PYRAZOLE-4-CARBOXYLIC ACID
2-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
[(3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] acetate
N-Cbz-Piperidine-2-carboxylic acid
C14H17NO4 (263.11575220000003)
1-benzyl 2-Methyl pyrrolidine-1,2-dicarboxylate
C14H17NO4 (263.11575220000003)
(1S,4R)-cis-4-Amino-2-cyclopentene-1-methanol D-Tartrate
(d)-n-(benzyloxycarbonyl)pipecolic acid
C14H17NO4 (263.11575220000003)
(l)-n-(benzyloxycarbonyl)pipecolic acid
C14H17NO4 (263.11575220000003)
tert-butyl 6-methoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate
N-(2-chloro-6-formylpyridin-3-yl)pivalamide
C13H17N3O3 (263.12698520000004)
Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate
(S)-1-Benzyl 2-methyl pyrrolidine-1,2-dicarboxylate
C14H17NO4 (263.11575220000003)
((3AR,4R,6AS)-5-BENZYL-2,2-DIMETHYLTETRAHYDRO-3AH-[1,3]DIOXOLO[4,5-C]PYRROL-4-YL)METHANOL
tert-butyl 6-hydroxy-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
4-[2-(2-hydroxyethyl)-1-benzofuran-5-yl]benzonitrile
4,4,5,5-tetramethyl-2-(2-methyl-5-nitrophenyl)-1,3,2-dioxaborolane
1-BOC-2,3-DIHYDRO-INDOLE-3-CARBOXYLIC ACID
C14H17NO4 (263.11575220000003)
4,4,5,5-Tetramethyl-2-(2-methyl-3-nitrophenyl)-1,3,2-dioxaborolane
4-Piperidinecarboxylicacid, 4-hydroxy-1-(phenylmethyl)-, ethyl ester
N-(5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIMIDIN-2-YL)ACETAMIDE
2-Butoxy-5-(trifluoromethyl)pyridine-3-boronic acid
2-Isobutoxy-5-(trifluoromethyl)pyridine-3-boronic acid
1-(6-METHYLPYRIDIN-2-YL)-2-(QUINOXALIN-6-YL)ETHANONE
2-[3-(Benzyloxy)phenyl]ethanamine hydrochloride (1:1)
2-(1-(Benzyloxycarbonyl)pyrrolidin-2-yl)acetic acid
C14H17NO4 (263.11575220000003)
tert-butyl 7-hydroxy-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylate
Benzyl 1,4-dioxa-7-azaspiro[4.4]nonane-7-carboxylate
C14H17NO4 (263.11575220000003)
PIPERAZINE-1-CARBOXYLIC ACID (4-ISOPROPOXY-PHENYL)-AMIDE
(3-(((1R,4R)-4-HYDROXYCYCLOHEXYL)CARBAMOYL)PHENYL)BORONIC ACID
3-benzyl-7-cyano-2,3,4,5-tetrahydro-1h-benzodiazepine
ETHYL 2,5-DIMETHYL-1-(2-THIENYLMETHYL)-1H-PYRROLE-3-CARBOXYLATE
5-(Methoxycarbonyl)pyridine-3-boronic acid pinacol ester
(S)-ETHYL 4-BENZYL-5-OXOMORPHOLINE-3-CARBOXYLATE
C14H17NO4 (263.11575220000003)
[1-(2-amino-phenyl)-azetidin-3-yl]-carbamic acid tert-butyl ester
1-PIPERIDINECARBOXYLIC ACID, 3-(2-PYRIMIDINYL)-, 1,1-DIMETHYLETHYL ESTER
4-(2-Pyrimidinyl)-1-piperidinecarboxylic acid 1,1-dimethylethyl ester
ETHYL 1-(2-HYDROXYMETHYLPHENYL)PIPERIDINE-4-CARBOXYLATE
(4-Oxo-4-phenyl-butyl)-carbamic acid tert-butylester
ETHYL 1-(4-(HYDROXYMETHYL)PHENYL)PIPERIDINE-3-CARBOXYLATE
tert-butyl 7-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1h)-carboxylate
4,4,5,5-tetramethyl-2-(3-methyl-4-nitrophenyl)-1,3,2-dioxaborolane
Pinacidil hydrate
C78274 - Agent Affecting Cardiovascular System > C270 - Antihypertensive Agent D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents D049990 - Membrane Transport Modulators
2-ISOPROPOXY-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE
C14H22BNO3 (263.16926520000004)
4-ethyl-3-[(4-ethylphenoxy)methyl]-1H-1,2,4-triazole-5-thione
(2S,4S)-1-TERT-BUTYL 2-METHYL 4-CHLOROPYRROLIDINE-1,2-DICARBOXYLATE
1-(2-Methyl-2-propanyl)-5-nitro-1H-pyrrolo[2,3-b]pyridine-3-carbo xylic acid
tert-Butyl (3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbamate
C13H17N3O3 (263.12698520000004)
5,5-(1,7-Dioxa-4,10-diazacyclododecane-4,10-diyl)bis(2,4-dimethy l-5-oxopentanoic acid)
1-(2,2-DIMETHOXY-ETHYL)-4-ETHYL-1H-INDOLE-2,3-DIONE
C14H17NO4 (263.11575220000003)
N-(4-nitrophenyl)-2-piperidin-1-ylacetamide
C13H17N3O3 (263.12698520000004)
(R)-Benzyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate
C14H17NO4 (263.11575220000003)
1-METHYL-3-(((1-METHYL-1H-PYRAZOL-4-YL)METHYL)CARBAMOYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID
2-(4-METHOXYPHENYL)-2-PHENYLETHYLAMINE HYDROCHLORIDE
2-Chloro-1-(2,2,4,7-tetramethyl-2H-quinolin-1-yl)-ethanone
1 2 3 4-TETRAHYDRO-9-ACRIDINECARBOXYLIC&
C14H17NO4 (263.11575220000003)
tert-butyl 3-amino-4-methoxyindazole-1-carboxylate
C13H17N3O3 (263.12698520000004)
DL-5-Benzoylamino-5-isopropyl-4-oxo-1,3-dioxane
C14H17NO4 (263.11575220000003)
6-AMINO-5-OXO-[1,4]DIAZEPANE-1-CARBOXYLICACIDBENZYLESTER
C13H17N3O3 (263.12698520000004)
2-Propoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
C14H22BNO3 (263.16926520000004)
2-Methyl-2-propanyl [1-(2-oxiranyl)-2-phenylethyl]carbamate
3-Methoxyphenylboronic acid MIDA ester
C12H14BNO5 (263.09649840000003)
5-Isopropoxypyridine-3-boronic acid pinacol ester
C14H22BNO3 (263.16926520000004)
METHYL 6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)NICOTINATE
(S)-1-(TERT-BUTOXYCARBONYL)INDOLINE-2-CARBOXYLIC ACID
C14H17NO4 (263.11575220000003)
2-(tert-Butoxycarbonyl)isoindoline-1-carboxylicacid
C14H17NO4 (263.11575220000003)
2-(4-(Hydroxymethyl)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione
C12H14BNO5 (263.09649840000003)
1-BENZYL 3-METHYL PYRROLIDINE-1,3-DICARBOXYLATE
C14H17NO4 (263.11575220000003)
Benzoic acid,2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)
3-(3,4-DIHYDROISOQUINOLIN-2(1H)-YL)PROPAN-1-OL
C14H17NO4 (263.11575220000003)
(Z)-4-(2-METHYLBENZYLIDENE)-2-PHENYLOXAZOL-5(4H)-ONE
5-(TERT-BUTYL)-3,3-DIMETHYL-6-NITROBENZOFURAN-2(3H)-ONE
C14H17NO4 (263.11575220000003)
Tetrahydrozoline nitrate
C13H17N3O3 (263.12698520000004)
2-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-dihydroisoindole-5-carboxylic acid
C14H17NO4 (263.11575220000003)
1-(4-METHOXY-BENZOYL)-PIPERIDINE-4-CARBOXYLIC ACID
C14H17NO4 (263.11575220000003)
Propanedioic acid,2-[(phenylamino)methylene]-, 1,3-diethyl ester
C14H17NO4 (263.11575220000003)
(1R,2S)-cis-2-(Boc-aMino)-1,2,3,4-tetrahydro-1-naphthol
2-(Methoxycarbonyl)-4-pyridineboronic acid, pinacol ester
{3-[(2,4-Dimethylphenoxy)methyl]-phenyl}amine hydrochloride
(1R,2R)-trans-2-(Boc-aMino)-1,2,3,4-tetrahydro-1-naphthol
1-Propanone,3-(dimethylamino)-1-(2-naphthalenyl)-, hydrochloride (1:1)
Ethyl 5-amino-1-(2-fluorobenzyl)-1H-pyrazole-3-carboxylate
1-[(TERT-BUTOXY)CARBONYL]-2,3-DIHYDRO-1H-INDOLE-5-CARBOXYLIC ACID
C14H17NO4 (263.11575220000003)
1-O-benzyl 3-O-methyl 3-methylazetidine-1,3-dicarboxylate
C14H17NO4 (263.11575220000003)
TERT-BUTYL8-HYDROXY-4,5-DIHYDRO-1H-BENZO[C]AZEPINE-2(3H)-CARBOXYLATE
2-Propoxypyridine-3-boronic acid pinacol ester
C14H22BNO3 (263.16926520000004)
1-(3-METHYL-PYRIDIN-2-YLMETHYL)-PIPERAZINE DI-HYDROCHLORIDE
C11H19Cl2N3 (263.09559540000004)
1H-Benz[g]indole-3-carboxaldehyde,2-cyclopentyl-(9CI)
ETHYL 8-METHOXY-2-OXO-2,3,4,5-TETRAHYDRO-1H-BENZO[B]AZEPINE-4-CARBOXYLATE
C14H17NO4 (263.11575220000003)
ETHYL 2-(N-BENZOYLAMINOMETHYL)-3-OXOBUTYRATE
C14H17NO4 (263.11575220000003)
Ethyl 5-[(4-methylpiperazin-1-yl)-methyl]pyridine-2-carboxylate
1-Piperidinecarboxylic acid, 4-(Methylsulfonyl)-, 1,1-dimethylethyl ester
1,2,3,6-TETRAHYDRO-1-METHYL-4-(2,4,6-TRIMETHOXYPHENYL)-PYRIDINE
1-(4-ethoxybenzoyl)pyrrolidine-2-carboxylic acid
C14H17NO4 (263.11575220000003)
7-Amino-4-Boc-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine
TERT-BUTYL 6-METHOXY-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE
METHYL 6-HYDROXY-7-(2-METHYLALLYL)-5-OXO-1,2,3,5-TETRAHYDROINDOLIZINE-8-CARBOXYLATE
C14H17NO4 (263.11575220000003)
[1-(3-amino-phenyl)-azetidin-3-yl]-carbamic acid tert-butyl ester
4-(diethylamino)benzenediazonium tetrafluoroborate
(R)-1-((Benzyloxy)carbonyl)piperidine-3-carboxylic acid
C14H17NO4 (263.11575220000003)
(4-(((1R,4R)-4-HYDROXYCYCLOHEXYL)CARBAMOYL)PHENYL)BORONIC ACID
1-(tert-Butoxycarbonyl)-2-indolinecarboxylic acid
C14H17NO4 (263.11575220000003)
(2S)-2-cyclohexyl-2-(pyrazine-2-carbonylamino)acetic acid
C13H17N3O3 (263.12698520000004)
4-phenyl-4,10-dihydro-[1,3,5]triazino[1,2-a]benzimidazol-2-amine
Gacyclidine
D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018691 - Excitatory Amino Acid Antagonists D002491 - Central Nervous System Agents > D018696 - Neuroprotective Agents C26170 - Protective Agent > C1509 - Neuroprotective Agent D020011 - Protective Agents
3-Hydroxy-4-(3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-piperidin-2-one
Pyridoxatin
A member of the class of dihydroxypyridines that is 1,4-dihydroxypyridin-2-one carrying an additional 6-ethenyl-2,4-dimethylcyclohexyl substituent at position 3. Pyridoxatin is a MMP-2 (Gelatinase A) inhibitor with antibiotic and anticancer properties. Also indicated to be a lipid peroxidation and DNA synthesis inhibitor as well as a free radical scavenger.
1-benzyl-3-pyridin-3-yl-1H-pyrazole-4-carbaldehyde
N-methyl-6-phenyl-3-(2-pyridinyl)-1,2,4-triazin-5-amine
2-[3-(4-Cyanoanilino)-1-(dimethylamino)-2-propenylidene]malononitrile
Naphthalene, decahydro-1-isothiocyanato-4a-methyl-8-methylene-2-(1-methylethyl)-, (1alpha,2beta,4aalpha,8aalpha)-
8-(Pyrimidin-2-ylamino)naphthalene-2-carboximidamide
Ethyl 4-[(4-methylpyridin-2-yl)amino]piperidine-1-carboxylate
(R)-1-(4-(4-(Hydroxymethyl)-1,3,2-dioxaborolan-2-YL)phenethyl)guanidine
4-Amino-2-hexyloxy-6-hydroxymethyl-tetrahydro-pyran-3,5-diol
Olaquindox
C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent
4-(5-Phenyl-1,2-oxazol-3-yl)benzenecarboximidamide
N(2)-phenylacetyl-L-glutaminate
An N-acyl-L-alpha-amino acid anion that is the conjugate base of N(2)-phenylacetyl-L-glutamine; major species at pH 7.3.
pentalenolactone D(1-)
A monocarboxylic acid anion that is the conjugate base of pentalenolactone D, obtained by deprotonation of the carboxy group; major species at pH 7.3.
(1S,4aR,9aR)-1,8,8-trimethyl-3-oxo-1,4,4a,6a,7,9-hexahydropentaleno[6a,1-c]pyran-5-carboxylate
[2-(4-Amino-3-hydroxybutanoyl)oxy-3-carboxypropyl]-trimethylazanium
2-Tert-butyl-6,7-dimethoxy-3,1-benzoxazin-4-one
C14H17NO4 (263.11575220000003)
(3S)-3-(1,3-dihydroxypentoxy)-4-(trimethylazaniumyl)butanoate
(3,5-Dimethyl-1-pyrazolyl)-(2-ethyl-4-nitro-3-pyrazolyl)methanone
N(6)-L-Homocysteinyl-L-lysine
C10H21N3O3S (263.13035560000003)
An N(6)-acyl-L-lysine derivative in which the acyl group is L-homocysteinyl.
5-Methyl-5-pentyl-2-phenyl-1,2,4-triazolidine-3-thione
N-[2-(4-methoxyphenyl)ethyl]-2,3-dihydro-1,4-dioxin-5-carboxamide
C14H17NO4 (263.11575220000003)
(1,4,8,11-Tetraazacyclotetradecane)copper(2+)
C10H24CuN4+2 (263.12968539999997)
neopentalenolactone D(1-)
A monocarboxylic acid anion that is the conjugate base of neopentalenolactone D, obtained by deprotonation of the carboxy group; major species at pH 7.3.
4-[(2-Ethyl-1-oxobutyl)amino]benzoic acid ethyl ester
N6-ethyl-N4-propan-2-yl-N2-(1,2,4-triazol-4-yl)-1,3,5-triazine-2,4,6-triamine
2-(3-Methylphenoxy)acetic acid (1-methyl-4-piperidinyl) ester
6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoate
C16H23O3- (263.16471079999997)
1-butyl-3-[(E)-(2,5-dimethylphenyl)methylideneamino]thiourea
(3Z)-dodec-3-en-1-yl sulfate
An organosulfate oxoanion that is the conjugate base of (3Z)-dodec-3-en-1-yl hydrogen sulfate. It has been isolated from Daphnia pulex and has been shown to cause morphological changes in the green alga Scenedesmus gutwinskii.
4-tert-butyl-2-{(2E)-2-[(5-methylfuran-2-yl)methylidene]hydrazinyl}-1,3-thiazole
N-propan-2-yl-2-[4-(2-pyrimidinyl)-1-piperazinyl]acetamide
(E)-2-(6-methyl-1H-benzimidazol-2-yl)-3-(5-methylfuran-2-yl)prop-2-enenitrile
(3R)-5-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-3-hydroxypentanoate
C11H19O7- (263.11307239999996)
(3S,4R)-4-[(2S,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-3-hydroxypentanoate
C11H19O7- (263.11307239999996)
Benzylmethylamino-1,2-bis(methoxycarbonyl)ethylene
C14H17NO4 (263.11575220000003)
1-Benzyl-2,2,6,6-tetramethyl-2,6-disilapiperidine
C14H25NSi2 (263.15254500000003)
N-(1-Cyclopropylethyl)-2-methoxyaniline, TMS derivative
8-Methoxy-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one, TMS derivative
1-(4-Chlorobutyl)-2,2,6,6-tetramethyl-2,6-disilapiperidine
N-(Benzylidene)bis(trimethylsilyl)methylamine
C14H25NSi2 (263.15254500000003)
(1S)-N-(1-Phenylethyl)-3-acetoxy-2,2-dimethylpropanamide
5-Acetyl-3-[(diethoxyphosphinyl)methyl]-2-isoxazoline
C10H18NO5P (263.09225480000003)
7-[3-(ethylamino)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile
N-(N-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)carbamimidoyl)-N-methylglycine
4-O-(beta-L-Araf)-cis-L-Hyp zwitterion
An amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of 4-O-(beta-L-Araf)-cis-L-Hyp.
Dioxoaminopyrine
C13H17N3O3 (263.12698520000004)
A monocarboxylic acid amide that is N,N-dimethyl-2-oxoacetamide substituted by a 2-acetyl-2-methyl-1-phenylhydrazinyl group at position 2. It is a metabolite of the drug aminopyrine.
RV01
RV01 is an analogue of resveratrol, inhibits DNA damage, reduces acetaldehyde dehydrogenase 2 (ALDH2) mRNA expression induced by ethanol, and exhibits hydroxyl radical scavenging activity[1]. RV01 decreases iNOS expression, with anti-neuroinflammatory activity[2].
(1r,4r,4ar,6s)-4-isopropyl-6-isothiocyanato-1,6-dimethyl-2,3,4,4a,5,7-hexahydro-1h-naphthalene
7-isopropyl-2-isothiocyanato-2,10-dimethylspiro[4.5]dec-6-ene
1-hydroxy-3-(4-hydroxyphenyl)-4-(2-methylpropyl)pyrrolidine-2,5-dione
C14H17NO4 (263.11575220000003)