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Showing Compound Substance P (FDB002259)

Record Information
Version1.0
Creation date2010-04-08 22:05:18 UTC
Update date2019-11-26 02:57:14 UTC
Primary IDFDB002259
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSubstance P
DescriptionEntamoeba histolytica is a single-celled parasitic protozoan that infects the lower gastrointestinal tract of humans. The symptoms of infection are diarrhea, constipation, and abdominal pain. This protozoan was found to secrete serotonin as well as substance P and neurotensin.; In the field of neuroscience, substance P (SP) is a neuropeptide: an undecapeptide that functions as a neurotransmitter and as a neuromodulator. It belongs to the tachykinin neuropeptide family. Substance P and its closely related neuropeptide neurokinin A (NKA) are produced from a polyprotein precursor after differential splicing of the preprotachykinin A gene. The deduced amino acid sequence of substance P is as follows:; Substance P (SP), is an 11-amino acid neuropeptide. SP is a member of the tachykinin family of peptides because it induces rapid smooth muscle contraction in guinea pig ileum and rat duodenum. Other members of the tachykinin family, sharing common carboxyl terminal Phe-X-Gly-Leu-met-NH2 sequences in mammals, include neurokinin A and neurokinin B. In mammals, tachykinins are produced by two genes, preprotachykinin-A (PPT-A) and preprotachykinin-B (PPT-B), and SP is a product of the PPT-A gene. SP is localized in the central nervous system as well as in several peripheral tissues, including the entire length of the gastrointestinal tract as well as the colon. The main sources of SP in the gut include the myenteric and submucosal plexus, intrinsic sensory neurons, as well as sensory neurons originating from the dorsal root ganglia. A newly identified gene, preprotachykinin C gene, encodes for the sequence of a new preprotachykinin protein designated hemokinin (HK) and produced primarily by hematopoietic cells. HK binds with high selectivity to NK-1R and has similar in vivo potency to SP. Like SP, HK is an 11-amino acid peptide having ~55% amino acid similarity to SP.; The effects of SP are mediated by three different G-protein-coupled receptors (GPCRs), namely neurokinin (NK)-1, 2, and 3. SP binds with high affinity to NK-1 receptor (NK-1R), and with low affinity to NK-2 and 3 receptors. NK-1 receptors are present in both small intestine and colon of animals and humans and are localized in a variety of cells, including nerves, smooth muscle, immune cells, glands, endothelial cells, as well as epithelial cells. Although NK-1 receptors have been associated with several intestinal pathophysiologic conditions (see below), NK-2 receptors have been linked mostly with circular muscle contraction, and are localized in circular muscle and muscularis mucosae. Although NK-2 receptors are present predominantly on smooth muscle and, like NK-1, can affect gut motility, NK-3 receptors are expressed predominantly in neurons and can stimulate or diminish muscle contraction indirectly following SP binding to neuronal cells in the submucosal and myenteric nerve plexuses of the gastrointestinal tract. NK-3 receptors also provide slow excitatory synaptic input to neurons in ganglia of the sphincter of Oddi. Thus, both NK-2 and NK-3 receptors affect motility responses in the GI, but there is very little evidence that they are involved in neuroimmune interactions. (PMID: 17192554); Substance P is an important element in pain perception. The sensory function of substance P is thought to be related to the transmission of pain information into the central nervous system. Substance P coexists with the excitatory neurotransmitter glutamate in primary afferents that respond to painful stimulation. SP has been associated with the regulation of mood disorders, anxiety, stress, reinforcement, neurogenesis, respiratory rhythm, neurotoxicity, nausea/emesis, pain and nociception. Substance P and other sensory neuropeptides can be released from the peripheral terminals of sensory nerve fibers in the skin, muscle and joints. It is proposed that this release is involved in neurogenic inflammation which is a local inflammatory response to certain types of infection or injury. The regulatory function of SP also involves the regulation of its high-affinity receptor, NK-1. Substance P receptor antagonists may have important therapeutic applications in the treatment of a variety of stress-related illnesses, in addition to their potential as analgesics. Substance P is found in common wheat.
CAS Number33507-63-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP-0.15ALOGPS
logP-5.8ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)11.49ChemAxon
pKa (Strongest Basic)11.9ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area516.63 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity362.14 m³·mol⁻¹ChemAxon
Polarizability141.28 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC63H98N18O13S
IUPAC name(2S)-2-[(2R)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2R)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}hexanoyl]pyrrolidin-2-yl]formamido}-4-carbamoylbutanamido]-N-[(1R)-1-{[(1R)-1-[({[(1R)-1-{[(1S)-1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-phenylethyl]carbamoyl}-2-phenylethyl]pentanediamide
InChI IdentifierInChI=1S/C63H98N18O13S/c1-37(2)33-45(57(89)74-41(53(68)85)27-32-95-3)73-52(84)36-72-54(86)46(34-38-15-6-4-7-16-38)78-58(90)47(35-39-17-8-5-9-18-39)79-56(88)42(23-25-50(66)82)75-55(87)43(24-26-51(67)83)76-59(91)49-22-14-31-81(49)62(94)44(20-10-11-28-64)77-60(92)48-21-13-30-80(48)61(93)40(65)19-12-29-71-63(69)70/h4-9,15-18,37,40-49H,10-14,19-36,64-65H2,1-3H3,(H2,66,82)(H2,67,83)(H2,68,85)(H,72,86)(H,73,84)(H,74,89)(H,75,87)(H,76,91)(H,77,92)(H,78,90)(H,79,88)(H4,69,70,71)/t40-,41-,42-,43+,44-,45+,46+,47+,48+,49-/m0/s1
InChI KeyADNPLDHMAVUMIW-SGTHPBLKSA-N
Isomeric SMILESCSCC[C@H](NC(=O)[C@@H](CC(C)C)NC(=O)CNC(=O)[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CCC(N)=O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCNC(N)=N)C(N)=O
Average Molecular Weight1347.63
Monoisotopic Molecular Weight1346.728146002
Classification
Description Belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentTocopherols
Alternative Parents
Substituents
  • Tocopherol
  • Diterpenoid
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02wa-1319101010-209f8038eedc515a4d6f2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ta-2729101110-7d4d3932d047407e12182016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02mj-9835202000-3628a96e37d0d507d9c72016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f92-6079000000-c6a896a4135dad2d46202016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9133000000-514803d766a0083241282016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9101000000-1af52acc0df0cbc52a652016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0129000100-2f2b29bac4d06feba2322021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007o-7595010000-13664c74323543ccdd592021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03k9-9320000120-1079eed36e2a21c18dea2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-2049000000-4cebe1eb15b90be2040a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-9025000000-5643582ce890212146292021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002g-9720010000-9e20245db6eb8a6287f32021-09-24View Spectrum
NMRNot Available
ChemSpider ID23215821
ChEMBL IDCHEMBL216421
KEGG Compound IDNot Available
Pubchem Compound ID44359816
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB05875
HMDB IDHMDB01897
CRC / DFC (Dictionary of Food Compounds) IDCHW48-Q:CHW48-Q
EAFUS IDNot Available
Dr. Duke IDSP
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSubstance P
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Common wheatExpected but not quantifiedNot AvailableDUKE
AnatidaeExpected but not quantifiedNot AvailableHMDB
BeefaloExpected but not quantifiedNot AvailableHMDB
BisonExpected but not quantifiedNot AvailableHMDB
BuffaloExpected but not quantifiedNot AvailableHMDB
Cattle (Beef, Veal)Expected but not quantifiedNot AvailableHMDB
ChickenExpected but not quantifiedNot AvailableHMDB
Columbidae (Dove, Pigeon)Expected but not quantifiedNot AvailableHMDB
DeerExpected but not quantifiedNot AvailableHMDB
Domestic goatExpected but not quantifiedNot AvailableHMDB
Showing 1 to 10 of 30 entries
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).