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Record Information
Version1.0
Created at2022-06-29 21:43:31 UTC
Updated at2022-06-29 21:43:31 UTC
NP-MRD IDNP0140621
Secondary Accession NumbersNone
Natural Product Identification
Common NameForsythoside A
DescriptionForsythoside A, also known as forsythiaside, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Forsythoside A is found in Calceolaria plectranthifolia, Digitalis purpurea, Forsythia europaea, Forsythia koreana, Forsythia suspensa, Forsythia viridissima, Globularia alypum, Veronica stricta, Penstemon linarioides, Rehmannia glutinosa and Syringa vulgaris. It was first documented in 2022 (PMID: 35850836). Based on a literature review a significant number of articles have been published on Forsythoside A (PMID: 35733131) (PMID: 35637849) (PMID: 35537260) (PMID: 35533916).
Structure
Thumb
Synonyms
ValueSource
ForsythiasideMeSH
Chemical FormulaC29H36O15
Average Mass624.5920 Da
Monoisotopic Mass624.20542 Da
IUPAC Name(2R,3S,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Traditional Nameforsythiaside
CAS Registry NumberNot Available
SMILES
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OCCC3=CC(O)=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C29H36O15/c1-13-22(35)23(36)25(38)29(42-13)41-12-20-27(44-21(34)7-4-14-2-5-16(30)18(32)10-14)24(37)26(39)28(43-20)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27+,28+,29+/m0/s1
InChI KeyDTOUWTJYUCZJQD-UJERWXFOSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Calceolaria plectranthifoliaLOTUS Database
Digitalis purpureaLOTUS Database
Forsythia europaeaLOTUS Database
Forsythia koreanaLOTUS Database
Forsythia suspensaLOTUS Database
Forsythia viridissimaLOTUS Database
Globularia alypumLOTUS Database
Hebe strictaLOTUS Database
Penstemon linarioidesLOTUS Database
Rehmannia glutinosaLOTUS Database
Syringa vulgarisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tyrosol derivative
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Polyol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.1ALOGPS
logP0.82ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.01ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area245.29 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity148.4 m³·mol⁻¹ChemAxon
Polarizability61.33 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002744
Chemspider ID4445086
KEGG Compound IDC10456
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281773
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Liu Y, Luo J, Gu YZ, Luo Y, Tan T, Liao ZG, Yang M: [Comparative analysis of powder and piece decocting processes of Yinqiao Powder based on determination of multiple primary components]. Zhongguo Zhong Yao Za Zhi. 2022 Jul;47(14):3788-3797. doi: 10.19540/j.cnki.cjcmm.20210913.302. [PubMed:35850836 ]
  2. Zheng X, Chen Z, Shi S, Yan H, Zhou J, Jiang L, Wang H, Hou G, Jiang Z: Forsythiaside A improves Influenza A virus infection through TLR7 signaling pathway in the lungs of mice. BMC Complement Med Ther. 2022 Jun 22;22(1):164. doi: 10.1186/s12906-022-03644-8. [PubMed:35733131 ]
  3. Bibi S, Khan MS, El-Kafrawy SA, Alandijany TA, El-Daly MM, Yousafi Q, Fatima D, Faizo AA, Bajrai LH, Azhar EI: Virtual screening and molecular dynamics simulation analysis of Forsythoside A as a plant-derived inhibitor of SARS-CoV-2 3CLpro. Saudi Pharm J. 2022 Jul;30(7):979-1002. doi: 10.1016/j.jsps.2022.05.003. Epub 2022 May 25. [PubMed:35637849 ]
  4. Zhang J, Xu X, Li L, Li H, Gao L, Yuan X, Du H, Guan Y, Zang H: Multi critical quality attributes monitoring of Chinese oral liquid extraction process with a spectral sensor fusion strategy. Spectrochim Acta A Mol Biomol Spectrosc. 2022 Oct 5;278:121317. doi: 10.1016/j.saa.2022.121317. Epub 2022 May 2. [PubMed:35537260 ]
  5. Liu C, Zhen D, Du H, Gong G, Wu Y, Ma Q, Quan ZS: Synergistic anti-inflammatory effects of peimine, peiminine, and forsythoside a combination on LPS-induced acute lung injury by inhibition of the IL-17-NF-kappaB/MAPK pathway activation. J Ethnopharmacol. 2022 Sep 15;295:115343. doi: 10.1016/j.jep.2022.115343. Epub 2022 May 6. [PubMed:35533916 ]