Symphytine (CHEM016157)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:17:12 UTC
Update Date2016-11-09 01:15:20 UTC
Accession NumberCHEM016157
Identification
Common NameSymphytine
ClassSmall Molecule
DescriptionA but-2-enoate ester obtained by formal condensation of the carboxy group of (2E)-2-methylbut-2-enoic acid with the 1-hydroxy group of (1R,7aR)-7-({oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-ol.
Contaminant Sources
  • IARC Carcinogens Group 3
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
7-Tiglyl-9-(-)-viridiflorylretronecineChEBI
7-Tiglylretronecine viridiflorateChEBI
7-Tiglylretronecine viridifloric acidGenerator
[(7R,8R)-7-[(e)-2-Methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoic acidGenerator
7-Tiglylretronecine viridiflateGenerator
7-Tiglylretronecine viridiflic acidGenerator
SymphytineMeSH
Chemical FormulaC20H31NO6
Average Molecular Mass381.469 g/mol
Monoisotopic Mass381.215 g/mol
CAS Registry Number22571-95-5
IUPAC Name(1R,7aR)-7-({[(2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2E)-2-methylbut-2-enoate
Traditional Namesymphytine
SMILES[H]\C(C)=C(\C)C(=O)O[C@]1([H])CCN2CC=C(COC(=O)[C@](O)(C(C)C)[C@]([H])(C)O)[C@]12[H]
InChI IdentifierInChI=1S/C20H31NO6/c1-6-13(4)18(23)27-16-8-10-21-9-7-15(17(16)21)11-26-19(24)20(25,12(2)3)14(5)22/h6-7,12,14,16-17,22,25H,8-11H2,1-5H3/b13-6+/t14-,16+,17+,20-/m0/s1
InChI KeyMVWPTZQHBOWRTF-SMLWLWDZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Alkaloid or derivatives
  • Pyrrolizine
  • Beta-hydroxy acid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Fatty acyl
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Pyrroline
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • 1,2-diol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
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 Solubility4.05 g/LALOGPS
logP2.09ALOGPS
logP1.92ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)11.34ChemAxon
pKa (Strongest Basic)7.14ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area96.3 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity101.77 m³·mol⁻¹ChemAxon
Polarizability41.07 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-4479000000-5217b0e8be9a2e358b45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-008d-9440000000-5cd3a0138e10c50ca139Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-9700000000-5f2eb08f8b9a61307483Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00m0-2529000000-664bae0257eeb2396484Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07cm-4945000000-2e6d7cd8a3a1f3025b72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01b9-7900000000-e77cf13f42074cc0c790Spectrum
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 IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00002123
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID9375
PubChem Compound ID5281754
Kegg Compound IDC10409
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11430014
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15482618
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17401847
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=287835
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=6579012
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=7128756
7.