Record Information
Version1.0
Creation date2010-04-08 22:05:14 UTC
Update date2020-02-24 19:10:25 UTC
Primary IDFDB002111
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSystemin
DescriptionSystemin belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues. Systemin has been detected, but not quantified in, garden tomatoes (Solanum lycopersicum). This could make systemin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Systemin.
CAS Number137181-56-7
Structure
Thumb
Synonyms
SynonymSource
(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
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC85H144N26O28S
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
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
Isomeric 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
Average Molecular Weight2010.275
Monoisotopic Molecular Weight2009.036408844
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 50.79%; H 7.22%; N 18.12%; O 22.28%; S 1.60%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0096-1100000109-0789fb136898de571445Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6x-6401001009-094834edce83f9f4f071Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-7911101202-bc23c5c3fddf1aaa7eb9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0lxw-2002002009-b313e29cf7f44d7b4785Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ow-3001002119-5683878233439cc1ec93Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f72-9012115224-85021853c03de97a9807Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-8001011009-5737216d5e07fa4fab49Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-3101101009-4a5bb44cb247da096ebaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9312000111-19db8df0af30c474d31aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1020000009-9b0c4b059a579f6eb8bfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-3201100019-123862a418aab7fc5223Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06sc-9602001003-48e7fbe06e20d08c26a1Spectrum
NMRNot Available
ChemSpider ID17287891
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID25078152
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30278
CRC / DFC (Dictionary of Food Compounds) IDCFN68-P:CFN68-P
EAFUS IDNot Available
Dr. Duke IDNot Available
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 IDSystemin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference