Nb-trans-p-Coumaroylserotonin glucoside (CHEM027087)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:29:25 UTC
Update Date2016-11-09 01:18:23 UTC
Accession NumberCHEM027087
Identification
Common NameNb-trans-p-Coumaroylserotonin glucoside
ClassSmall Molecule
DescriptionNb-trans-p-Coumaroylserotonin glucoside is found in fats and oils. It is an alkaloid from Carthamus tinctorius (safflower) If neurons that make serotonin serotonergic neurons are abnormal in infants, there is a risk of sudden infant death syndrome (SIDS). Low levels of serotonin may also be associated with intense spiritual experiences. In animals including humans, serotonin is synthesized from the amino acid L-tryptophan by a short metabolic pathway consisting of two enzymes: tryptophan hydroxylase (TPH) and amino acid decarboxylase (DDC). The TPH-mediated reaction is the rate-limiting step in the pathway. TPH has been shown to exist in two forms: TPH1, found in several tissues, and TPH2, which is a brain-specific isoform. There is evidence that genetic polymorphisms in both these subtypes influence susceptibility to anxiety and depression in humans.[citation needed] The 5-HTT gene regulates a chemical called serotonin. This chemical is found in very low amounts in people diagnosed with depression compared to other people. Serotonin works as a neurotransmitter and helps with the modulation of things such as anger, appetite, sexuality, sleep, mood, and several other things. People with depression often have impaired 5-HTT genes. There are two forms of the 5-HTT gene and everyone has two 5-HTT genes. (Levinson) There is a long form of 5-HTT and a short form of 5-HTT. Research shows that people with both 5-HTT genes being the long form are less likely to become depressed while people with one short and one long or two short forms are more likely to develop depression. Research is still being conducted to find more information. There is also evidence that ovarian hormones can affect the expression of TPH in various species, suggesting a possible mechanism for postpartum depression and premenstrual stress syndrome.[citation needed] Serotonin biosynthesis in plants likewise begins with L-tryptophan, which is however first decarboxylated by tryptophan decarboxylase to give tryptamine, which is then hydroxylated by the cytochrome P450 monooxygenase, tryptamine 5-hydroxylase, yielding serotonin. Serotonin is a biochemical messenger and regulator, synthesized from the essential amino acid L-Tryptophan. Serotonin in the nervous system acts as a local transmitter at synapses, and as a paracrine or hormonal modulator of circuits upon diffusion, allowing a wide variety of "state-dependent" behavioral responses to different stimuli. Serotonin is widely distributed in the nervous system of vertebrates and invertebrates and some of its behavioral effects have been preserved along evolution. Such is the case of aggressive behavior and rhythmic motor patterns , including those responsible for feeding. In vertebrates, which display a wider and much more sophisticated behavioral repertoire, serotonin also modulates sleep , the arousal state , sexual behavior, and others, and deficiencies of the serotonergic system causes disorders such as depression, obsessive-compulsive disorder, phobias, posttraumatic stress disorder, epilepsy, and generalized anxiety disorder. Serotonin has three different modes of action in the nervous system: as transmitter, acting locally at synaptic boutons; Serotonin is a monoamine neurotransmitter. It is found extensively in the gastrointestinal tract of animals, and about 80 to 90 percent of the human body's total serotonin is located in the enterochromaffin cells in the gut, where it is used to regulate intestinal movements. The remainder is synthesized in serotonergic neurons in the central nervous system (CNS) where it has various functions, including the regulation of mood, appetite, sleep, muscle contraction, and some cognitive functions including memory and learning. Serotonin levels can not be increased by diet alone. For example, increasing foods rich in tryptophan (e.g., meats, proteins) does not increase serotonin levels, due to competition with other amino acids. What is required to increase serotonin production is an increase in the ratio of tryptophan to phenylalanine and leucine. Fruits with a good ratio include dates, papaya and banana. Nb-trans-p-Coumaroylserotonin glucoside with a lower ratio inhibits the production of serotonin. These include whole wheat and rye bread. Research indicates that vigorous aerobic exercise improves mood through BDNF expression, there is however no direct evidence that this is caused by an increase in serotonin levels. Research also suggests that eating a diet rich in whole grain carbohydrates and low in protein will increase serotonin by secreting insulin, which helps in amino acid competition. However, increasing insulin for a long period of time can sometimes onset insulin resistance, which is related to obesity, type 2 diabetes, and lower serotonin levels. It is also believed that muscles use many of the amino acids except tryptophan, allowing men to have more serotonin than women. Bright light therapy may have an effect on blood serotonin levels. Nb-trans-p-Coumaroylserotonin glucoside is obtained by spending more time in natural sunlight.[citation needed] Recently, acupuncture has been shown to stimulate the release of serotonin in lab animals. upon diffusion at a distance from its release sites, producing paracrine (also called volume) effects, and by circulating in the blood stream, producing hormonal effects. The three modes can affect a single neuronal circuit. (PMID: 16047543).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-HydroxytryptamineHMDB
(2E)-3-(4-Hydroxyphenyl)-N-[2-(5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H-indol-3-yl)ethyl]prop-2-enimidateGenerator
Chemical FormulaC25H28N2O8
Average Molecular Mass484.498 g/mol
Monoisotopic Mass484.185 g/mol
CAS Registry Number76423-56-8
IUPAC Name(2E)-3-(4-hydroxyphenyl)-N-[2-(5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H-indol-3-yl)ethyl]prop-2-enamide
Traditional Name(2E)-3-(4-hydroxyphenyl)-N-[2-(5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H-indol-3-yl)ethyl]prop-2-enamide
SMILESOCC1OC(OC2=CC3=C(NC=C3CCNC(=O)\C=C\C3=CC=C(O)C=C3)C=C2)C(O)C(O)C1O
InChI IdentifierInChI=1S/C25H28N2O8/c28-13-20-22(31)23(32)24(33)25(35-20)34-17-6-7-19-18(11-17)15(12-27-19)9-10-26-21(30)8-3-14-1-4-16(29)5-2-14/h1-8,11-12,20,22-25,27-29,31-33H,9-10,13H2,(H,26,30)/b8-3+
InChI KeyLPGWQGDUKIPAME-FPYGCLRLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as arginine and derivatives. Arginine and derivatives are compounds containing arginine or a derivative thereof resulting from reaction of arginine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentArginine and derivatives
Alternative Parents
Substituents
  • Arginine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Carboxamide group
  • Guanidine
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Carboximidamide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Imine
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP1.48ALOGPS
logP0.79ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)9.42ChemAxon
pKa (Strongest Basic)1.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area164.5 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity126.34 m³·mol⁻¹ChemAxon
Polarizability50.82 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0wt9-4904500000-7f681c975d1b3246df79Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-5863009000-dd6871f89ea958ced31cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0309300000-3f1b6d41347895b2dce8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05di-0904000000-cf5b0108517530cf17e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01t9-0901000000-9961446d481b73d89012Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0089-1407900000-a68bed48f6fc85b1b603Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1809200000-7ae1a2b2ca34e8fe9429Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-022c-3912000000-bcd9e1f8db7bb0f76804Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0302900000-84b21c76d5c300b455b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-060r-4409500000-2a047eed990247822ad4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-1974000000-fbb87490537b975c096eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0207900000-9cf87fa1b955e857d906Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0309700000-4a12f17b8061f35d57a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-7902300000-45ddbf5f4fdeb36454abSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0032760
FooDB IDFDB010727
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID131751296
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. De-Miguel FF, Trueta C: Synaptic and extrasynaptic secretion of serotonin. Cell Mol Neurobiol. 2005 Mar;25(2):297-312.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.