Np mrd loader

Record Information
Version1.0
Created at2021-11-12 23:56:11 UTC
Updated at2021-11-26 17:46:26 UTC
NP-MRD IDNP0044191
Secondary Accession NumbersNone
Natural Product Identification
Common NameGastrodin
DescriptionGastrodin 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. Gastrodin is found in Anoectochilus formosanus, Anoectochilus koshunensis, Bletilla formosana, Citrullus colocynthis, Citrullus colocynthis (L.) , Cremastra appendiculata, Cyrtosia septentrionalis, Galeola faberi, Gastrodia elata , Gymnadenia conopsea, Helicia cochinchinensis, Dactylorhiza hatagirea, Origanum vulgare , Pyrus bourgaeana and Sicana odorifera. It was first documented in 2021 (PMID: 34685754). Based on a literature review a significant number of articles have been published on Gastrodin (PMID: 34718133) (PMID: 34603025) (PMID: 34581069) (PMID: 34541406).
Structure
Thumb
Synonyms
ValueSource
4-(Hydroxymethyl)phenyl-beta-D-glucopyranosideKegg
4-(Hydroxymethyl)phenyl-b-D-glucopyranosideGenerator
4-(Hydroxymethyl)phenyl-β-D-glucopyranosideGenerator
GastrodineMeSH
Chemical FormulaC13H18O7
Average Mass286.2800 Da
Monoisotopic Mass286.10525 Da
IUPAC Name(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
Traditional Namegastrodin
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](OC2=CC=C(CO)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C13H18O7/c14-5-7-1-3-8(4-2-7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1
InChI KeyPUQSUZTXKPLAPR-UJPOAAIJSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anoectochilus formosanusPlant
Anoectochilus koshunensisLOTUS Database
Bletilla formosanaLOTUS Database
Citrullus colocynthisLOTUS Database
Citrullus colocynthis (L.)Plant
Cremastra appendiculataLOTUS Database
Cyrtosia septentrionalisLOTUS Database
Galeola faberiLOTUS Database
Gastrodia elataPlant
Gymnadenia conopseaPlant
Helicia cochinchinensisPlant
Orchis hatagireaLOTUS Database
Origanum vulgarePlant
Pyrus bourgaeanaLOTUS Database
Sicana odoriferaLOTUS Database
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
  • Phenoxy compound
  • Benzyl alcohol
  • Phenol ether
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Aromatic alcohol
  • 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
logP-1.1ALOGPS
logP-1.4ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area119.61 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67 m³·mol⁻¹ChemAxon
Polarizability28.17 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00029516
Chemspider ID102977
KEGG Compound IDC16964
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGastrodin
METLIN IDNot Available
PubChem Compound115067
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDrw1667501
References
General References
  1. Bayan N, Yazdanpanah N, Rezaei N: Role of toll-like receptor 4 in diabetic retinopathy. Pharmacol Res. 2022 Jan;175:105960. doi: 10.1016/j.phrs.2021.105960. Epub 2021 Oct 28. [PubMed:34718133 ]
  2. Ting HC, Yang HI, Harn HJ, Chiu IM, Su HL, Li X, Chen MF, Ho TJ, Liu CA, Tsai YJ, Chiou TW, Lin SZ, Chang CY: Coactivation of GSK3beta and IGF-1 Attenuates Amyotrophic Lateral Sclerosis Nerve Fiber Cytopathies in SOD1 Mutant Patient-Derived Motor Neurons. Cells. 2021 Oct 16;10(10). pii: cells10102773. doi: 10.3390/cells10102773. [PubMed:34685754 ]
  3. Bai Y, Mo K, Wang G, Chen W, Zhang W, Guo Y, Sun Z: Intervention of Gastrodin in Type 2 Diabetes Mellitus and Its Mechanism. Front Pharmacol. 2021 Sep 16;12:710722. doi: 10.3389/fphar.2021.710722. eCollection 2021. [PubMed:34603025 ]
  4. Yan Y, Zhang YL, Jin XL, Liao X, Gong X, Chen WJ, Wei JJ, Fan XM, Piao JZ, Fu GJ, Guo CL: [Systematic review and Meta-analysis of efficacy and safety of gastrodin in treatment of tension-type headache]. Zhongguo Zhong Yao Za Zhi. 2021 Sep;46(18):4615-4622. doi: 10.19540/j.cnki.cjcmm.20210615.501. [PubMed:34581069 ]
  5. Yang H, Li Q, Li L, Chen S, Zhao Y, Hu Y, Wang L, Lan X, Zhong L, Lu D: Gastrodin modified polyurethane conduit promotes nerve repair via optimizing Schwann cells function. Bioact Mater. 2021 Jul 2;8:355-367. doi: 10.1016/j.bioactmat.2021.06.020. eCollection 2022 Feb. [PubMed:34541406 ]
  6. Chae, Sung-Wook et al. (2008). Three Phenolic Glycosides from Gastrodia elata. Journal of Applied Biological Chemistry, Volume 51 Issue 2, Pages.61-65 (2008). DOI: 10.3839/jabc.2008.011. Journal of Applied Biological Chemistry.