Showing Compound Card for Syringin (CDB000211)

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Record Information
Version1.0
Created at2020-03-18 23:28:53 UTC
Updated at2020-12-07 19:07:16 UTC
CannabisDB IDCDB000211
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameSyringin
DescriptionSyringin, also known as eleutheroside B or lilacin, was first isolated from the bark of lilac (Syringa vulgaris) by Meillet in 1841, where its name likely was derived. It belongs to the class of organic compounds known as phenolic glycosides. Phenolic glycosides are organic compounds containing a phenolic structure attached to a glycosyl moiety. Syringin results from the glycosidic bonding of sinapyl alcohol and glucose. Some examples of phenolic structures include lignans and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Syringin is neutral compound. Syringin is a naturally occurring organic compound found in many plants such as Eleutherococcus senticosus (Siberian ginseng), dandelion, coffee and cannabis (PMID:6991645 ). Syringin has also been detected in caraway, fennels, and lemons ( Ref:DOI ). Syringin have been reported to have immunomodulatory, anti-inflammatory, antinociceptive and hypoglucemic effects (PMID: 11578112 ; PMID: 15549657 ; PMID: 18203055 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-O-(beta-D-Glucosyl)-trans-4-sinapoyl alcoholChEBI
beta-TerpineolChEBI
Eleutheroside bChEBI
LigustrinChEBI
LilacinChEBI
MAGNOLENIN aChEBI
MethoxyconiferineChEBI
SyriginChEBI
SyringeninChEBI
SyringosideChEBI
4-O-(b-D-Glucosyl)-trans-4-sinapoyl alcoholGenerator
4-O-(Β-D-glucosyl)-trans-4-sinapoyl alcoholGenerator
b-TerpineolGenerator
Β-terpineolGenerator
Sinapyl alcohol 4-O-glucosideMeSH
Chemical FormulaC17H24O9
Average Molecular Weight372.37
Monoisotopic Molecular Weight372.142
IUPAC Name(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenoxy}oxane-3,4,5-triol
Traditional Namesyringin
CAS Registry Number118-34-3
SMILES
COC1=CC(\C=C\CO)=CC(OC)=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C17H24O9/c1-23-10-6-9(4-3-5-18)7-11(24-2)16(10)26-17-15(22)14(21)13(20)12(8-19)25-17/h3-4,6-7,12-15,17-22H,5,8H2,1-2H3/b4-3+/t12-,13-,14+,15-,17+/m1/s1
InChI KeyQJVXKWHHAMZTBY-GCPOEHJPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • O-glycosyl compound
  • Cinnamyl alcohol
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Methoxybenzene
  • Anisole
  • Phenoxy compound
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Secondary alcohol
  • Oxacycle
  • Ether
  • Acetal
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point192 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.32ALOGPS
logP-1.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area138.07 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity90.24 m³·mol⁻¹ChemAxon
Polarizability37.45 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSyringin, TMS_3_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-03di-0900000000-f96467539c41172c0acc2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-01ox-0921000000-3679abcaaec44614df3f2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-03ec-0930000000-ab5d3b3faf244f8425692020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-01si-0920000000-d6ca8e518f6c190453562020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-0002-0019000000-428ad645054e7ec9123a2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-004j-0098000000-68e6082813f13e72653d2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-0ue9-0190000000-7abbfb70a416aeca380c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-03di-0900000000-9332b89759063c39867d2020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08ml-0649000000-1dc5fb5d7d622ccf233c2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-0921000000-8261eb2a00fd30f2bd1c2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-2910000000-b3bc64b5eea585f493dd2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-1449000000-aebf03ec38a4451f44c62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6u-0932000000-e6cc56d8d4b8a740f13e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-3910000000-69c5b29e4a9ee146dd5a2016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011657
KNApSAcK IDC00030167
Chemspider IDNot Available
KEGG Compound IDC01533
BioCyc IDCPD-63
BiGG IDNot Available
Wikipedia LinkSyringin
METLIN IDNot Available
PubChem Compound5316860
PDB IDNot Available
ChEBI ID9380
References
General References
  1. Cho JY, Nam KH, Kim AR, Park J, Yoo ES, Baik KU, Yu YH, Park MH: In-vitro and in-vivo immunomodulatory effects of syringin. J Pharm Pharmacol. 2001 Sep;53(9):1287-94. doi: 10.1211/0022357011776577. [PubMed:11578112 ]
  2. Choi J, Shin KM, Park HJ, Jung HJ, Kim HJ, Lee YS, Rew JH, Lee KT: Anti-inflammatory and antinociceptive effects of sinapyl alcohol and its glucoside syringin. Planta Med. 2004 Nov;70(11):1027-32. doi: 10.1055/s-2004-832642. [PubMed:15549657 ]
  3. Niu HS, Liu IM, Cheng JT, Lin CL, Hsu FL: Hypoglycemic effect of syringin from Eleutherococcus senticosus in streptozotocin-induced diabetic rats. Planta Med. 2008 Feb;74(2):109-13. doi: 10.1055/s-2008-1034275. Epub 2008 Jan 17. [PubMed:18203055 ]
  4. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]