Systemin (CHEM024303)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:37:17 UTC
Update Date2016-11-09 01:17:52 UTC
Accession NumberCHEM024303
Identification
Common NameSystemin
ClassSmall Molecule
DescriptionSystemin is found in garden tomato. Systemin is a constituent of the leaves of tomato (Lycopersicon esculentum) Systemin is a plant hormone involved in wound response. It was the first plant hormone that was proven to be a peptide. Systemin induces the production of protease inhibitors which protect against insect herbivores
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3S)-4-[(2S)-1-[(2S)-1-[(2S)-2-{[(2S)-2-{[(2S)-6-amino-2-{[(2S)-2-({[(2S)-1-[(2S)-1-[(2S)-6-amino-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-1,3-dihydroxypropylidene]amino}hexanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1,3-dihydroxypropylidene]amino}-1-hydroxyhexylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-3-carboxypropanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyloxy]-3-{[(2S,3R)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-1,3-dihydroxybutylidene]amino}-4-oxobutanoateHMDB
(3S)-4-[(2S)-1-[(2S)-1-[(2S)-2-{[(2S)-2-{[(2S)-6-amino-2-{[(2S)-2-({[(2S)-1-[(2S)-1-[(2S)-6-amino-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-1,3-dihydroxypropylidene]amino}hexanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1,3-dihydroxypropylidene]amino}-1-hydroxyhexylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-3-carboxypropanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyloxy]-3-{[(2S,3R)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulphanyl)butylidene]amino}-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-1,3-dihydroxybutylidene]amino}-4-oxobutanoateHMDB
(3S)-4-[(2S)-1-[(2S)-1-[(2S)-2-{[(2S)-2-{[(2S)-6-amino-2-{[(2S)-2-({[(2S)-1-[(2S)-1-[(2S)-6-amino-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-1,3-dihydroxypropylidene]amino}hexanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1,3-dihydroxypropylidene]amino}-1-hydroxyhexylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-3-carboxypropanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyloxy]-3-{[(2S,3R)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulphanyl)butylidene]amino}-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-1,3-dihydroxybutylidene]amino}-4-oxobutanoic acidHMDB
Chemical FormulaC85H144N26O28S
Average Molecular Mass2010.275 g/mol
Monoisotopic Mass2009.036 g/mol
CAS Registry Number137181-56-7
IUPAC Name(3S)-4-[(2S)-1-[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-{[(2S)-1-[(2S)-1-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-methylbutanamido]-4-carbamoylbutanamido]-3-hydroxypropanamido]hexanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}-3-hydroxypropanamido]hexanamido]-5-[(diaminomethylidene)amino]pentanamido]-3-carboxypropanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyloxy]-3-[(2S,3R)-2-[(2S)-4-carbamoyl-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-4-(methylsulfanyl)butanamido]butanamido]-3-hydroxybutanamido]-4-oxobutanoic acid
Traditional Name(3S)-4-[(2S)-1-[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-{[(2S)-1-[(2S)-1-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-aminopropanamido]-3-methylbutanamido]-4-carbamoylbutanamido]-3-hydroxypropanamido]hexanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}-3-hydroxypropanamido]hexanamido]-5-[(diaminomethylidene)amino]pentanamido]-3-carboxypropanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyloxy]-3-[(2S,3R)-2-[(2S)-4-carbamoyl-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-4-(methylsulfanyl)butanamido]butanamido]-3-hydroxybutanamido]-4-oxobutanoic acid
SMILESCSCC[C@H](NC(=O)[C@@H](N)CCCCN)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(=O)OC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)N)C(C)C
InChI IdentifierInChI=1S/C85H144N26O28S/c1-43(2)65(106-67(121)44(3)89)77(131)100-49(25-27-61(91)115)71(125)104-55(41-112)75(129)101-52(19-8-11-32-88)79(133)109-35-14-22-58(109)81(135)108-34-13-21-57(108)76(130)105-56(42-113)74(128)98-47(18-7-10-31-87)69(123)97-48(20-12-33-95-85(93)94)70(124)102-53(39-63(117)118)80(134)110-36-15-23-59(110)82(136)111-37-16-24-60(111)84(138)139-83(137)54(40-64(119)120)103-78(132)66(45(4)114)107-73(127)50(26-28-62(92)116)99-72(126)51(29-38-140-5)96-68(122)46(90)17-6-9-30-86/h43-60,65-66,112-114H,6-42,86-90H2,1-5H3,(H2,91,115)(H2,92,116)(H,96,122)(H,97,123)(H,98,128)(H,99,126)(H,100,131)(H,101,129)(H,102,124)(H,103,132)(H,104,125)(H,105,130)(H,106,121)(H,107,127)(H,117,118)(H,119,120)(H4,93,94,95)/t44-,45+,46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,56-,57-,58-,59-,60-,65-,66-/m0/s1
InChI KeyHOWHQWFXSLOJEF-MGZLOUMQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
KingdomOrganic compounds
Super ClassOrganic Polymers
ClassPolypeptides
Sub ClassNot Available
Direct ParentPolypeptides
Alternative Parents
Substituents
  • Polypeptide
  • Alpha peptide
  • Glutamine or derivatives
  • Aspartic acid or derivatives
  • Methionine or derivatives
  • Tetracarboxylic acid or derivatives
  • N-acyl-alpha-amino acid
  • Valine or derivatives
  • Proline or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Serine or derivatives
  • Alanine or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • N-acylpyrrolidine
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxylic acid anhydride
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Guanidine
  • Amino acid
  • Primary carboxylic acid amide
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Dialkylthioether
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid derivative
  • Carboxylic acid
  • Carboximidamide
  • Primary amine
  • Primary aliphatic amine
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Primary alcohol
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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 Solubility0.17 g/LALOGPS
logP-2.1ALOGPS
logP-19ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.18ChemAxon
pKa (Strongest Basic)11.07ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count35ChemAxon
Hydrogen Donor Count26ChemAxon
Polar Surface Area889.78 ŲChemAxon
Rotatable Bond Count65ChemAxon
Refractivity492.8 m³·mol⁻¹ChemAxon
Polarizability205.46 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0096-1100000109-0789fb136898de571445Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6x-6401001009-094834edce83f9f4f071Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-7911101202-bc23c5c3fddf1aaa7eb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0lxw-2002002009-b313e29cf7f44d7b4785Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ow-3001002119-5683878233439cc1ec93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f72-9012115224-85021853c03de97a9807Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-8001011009-5737216d5e07fa4fab49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-3101101009-4a5bb44cb247da096ebaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9312000111-19db8df0af30c474d31aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1020000009-9b0c4b059a579f6eb8bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-3201100019-123862a418aab7fc5223Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06sc-9602001003-48e7fbe06e20d08c26a1Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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 IDHMDB0030278
FooDB IDFDB002111
Phenol Explorer IDNot Available
KNApSAcK IDC00055103
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSystemin
Chemspider ID17287891
ChEBI IDNot Available
PubChem Compound ID25078152
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Szekeres M: Brassinosteroid and systemin: two hormones perceived by the same receptor. Trends Plant Sci. 2003 Mar;8(3):102-4.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.