Np mrd loader

Record Information
Version2.0
Created at2022-04-28 06:06:06 UTC
Updated at2022-04-28 06:06:06 UTC
NP-MRD IDNP0061240
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Hydroxy-2-isopentenyl-3-methoxystilbene
DescriptionLongistylin C belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. 5-Hydroxy-2-isopentenyl-3-methoxystilbene is found in Cajanus cajan , Lonchocarpus chiricanus, Lonchocarpus longifolius, Lonchocarpus peninsularis and Lonchocarpus violaceus. 5-Hydroxy-2-isopentenyl-3-methoxystilbene was first documented in 2007 (PMID: 17211658). Based on a literature review a small amount of articles have been published on Longistylin C (PMID: 30653252) (PMID: 25908631) (PMID: 22242429) (PMID: 20064598).
Structure
Thumb
Synonyms
ValueSource
Longistyline CMeSH
Chemical FormulaC20H22O2
Average Mass294.3940 Da
Monoisotopic Mass294.16198 Da
IUPAC Name3-methoxy-4-(3-methylbut-2-en-1-yl)-5-[(E)-2-phenylethenyl]phenol
Traditional Name3-methoxy-4-(3-methylbut-2-en-1-yl)-5-[(E)-2-phenylethenyl]phenol
CAS Registry NumberNot Available
SMILES
COC1=C(CC=C(C)C)C(\C=C\C2=CC=CC=C2)=CC(O)=C1
InChI Identifier
InChI=1S/C20H22O2/c1-15(2)9-12-19-17(13-18(21)14-20(19)22-3)11-10-16-7-5-4-6-8-16/h4-11,13-14,21H,12H2,1-3H3/b11-10+
InChI KeyNFAWEPOBHKEHPO-ZHACJKMWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cajanus cajanPlant
Lonchocarpus chiricanusPlant
Lonchocarpus longifoliusPlant
Lonchocarpus peninsularisPlant
Lonchocarpus violaceusPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Styrene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
logP5.48ALOGPS
logP5.58ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)8.86ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.2 m³·mol⁻¹ChemAxon
Polarizability34.33 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00015604
Chemspider ID4950242
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6446720
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. He X, Zhang H, Liang X: Separation of six compounds from pigeon pea leaves by elution-extrusion counter-current chromatography. J Sep Sci. 2019 Mar;42(6):1202-1209. doi: 10.1002/jssc.201801111. Epub 2019 Feb 7. [PubMed:30653252 ]
  2. Shan Y, Hong T, Wang YF, Zhang NL, Yu B, Lu Y, Qiu SX: Synthesis and cytotoxicity of longistylin C derivatives. Chin J Nat Med. 2015 Apr;13(4):311-5. doi: 10.1016/S1875-5364(15)30021-2. [PubMed:25908631 ]
  3. Wang D, Xiao M, Li Y, Shen X, Lu Y, Liu K, Li Z, Hu Y: [Determination of longistylin A and longistylin C in Cajanus cajan]. Zhongguo Zhong Yao Za Zhi. 2011 Oct;36(19):2680-3. [PubMed:22242429 ]
  4. Ashidi JS, Houghton PJ, Hylands PJ, Efferth T: Ethnobotanical survey and cytotoxicity testing of plants of South-western Nigeria used to treat cancer, with isolation of cytotoxic constituents from Cajanus cajan Millsp. leaves. J Ethnopharmacol. 2010 Mar 24;128(2):501-12. doi: 10.1016/j.jep.2010.01.009. Epub 2010 Jan 11. [PubMed:20064598 ]
  5. Son IH, Chung IM, Lee SJ, Moon HI: Antiplasmodial activity of novel stilbene derivatives isolated from Parthenocissus tricuspidata from South Korea. Parasitol Res. 2007 Jun;101(1):237-41. doi: 10.1007/s00436-006-0454-y. Epub 2007 Jan 9. [PubMed:17211658 ]