Showing Compound Card for Orientin (CDB000104)

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Record Information
Version1.0
Created at2020-03-18 23:24:55 UTC
Updated at2020-12-07 19:07:06 UTC
CannabisDB IDCDB000104
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameOrientin
DescriptionOrientin, also known as lutexin, is an 8-C-glycosilated derivative of the flavonoid luteolin, substituted by beta-D-glucopyranosyl. Flavonoids are phenyl substituted chromones (benzopyran derivatives) consisting of a 15-carbon basic skeleton (C6-C3-C6), composed of a chroman (C6-C3) nucleus (the benzo ring A and the heterocyclic ring C; also shared by the tocopherols), with a phenyl (the aromatic ring B) substitution usually at the 2-position. Different substitutions can typically occur in the rings, A and B. 8-C-glycosilated flavonoids are compounds containing a carbohydrate moiety which is C-glycosidically linked to position 8 of a 2-phenylchromen-4-one flavonoid backbone. Orientin is a neutral compound. Orientin is a water-soluble flavonoid C-glycoside found in calcium tree, black bamboo, spelts, triticales, red rices, hard wheats, flaxseeds, wild apricot and cucumber; in barley, flax and tamarind leaves; in basil, blueberry, oregano plants; passion flower, the Açaí palm, buckwheat sprouts, and in millets. It is one of several dozen flavonoid glycosides that have been identified in low-THC Cannabis cultivars (PMID: 6991645 ). Flavonoids are polyphenolic compounds that are universally present as constituents of flowering plants, particularly of food plants. Several plants and spices containing flavonoid derivatives have found application as disease preventive and therapeutic agents in traditional medicine in Asia for thousands of years. The selection of a food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. The much lower risk of colon, prostate and breast cancers in Asians, who consume more vegetables, fruits and tea than populations in the Western hemisphere do, raises the question of whether flavonoid components mediate the protective effects of diets rich in these foodstuffs by acting as natural chemopreventive and anticancer agents. Orientin, extracted from different medicinal plants, exhibits antioxidant, anti-aging, anti-viral, anti-bacterial, anti-inflammation, vasodilatation and cardioprotective, radiation protective, neuroprotective, antidepressant-like, anti-adipogenesis, and anti-nociceptive effects that have been reviewed (PMID: 27298620 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
8-beta-D-GlucosylluteolinChEBI
Luteolin 8-C-glucosideChEBI
LutexinChEBI
8-b-D-GlucosylluteolinGenerator
8-Β-D-glucosylluteolinGenerator
8-C-beta-Glucopyranosyl-3',4',5,7-tetrahydroxyflav-2-en-3-oneMeSH
Chemical FormulaC21H20O11
Average Molecular Weight448.38
Monoisotopic Molecular Weight448.1006
IUPAC Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
Traditional Nameorientin
CAS Registry Number28608-75-5
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1
InChI KeyPLAPMLGJVGLZOV-VPRICQMDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 8-C-glycosides
Alternative Parents
Substituents
  • Flavonoid-8-c-glycoside
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • C-glycosyl compound
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Catechol
  • Phenol
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.34ALOGPS
logP-0.35ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)6.17ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area197.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity108.01 m³·mol⁻¹ChemAxon
Polarizability42.38 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-0002-0000900000-39ec184c48787a4ee3752020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, negativesplash10-0002-0005900000-01af12bfb51667c309942020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, negativesplash10-004i-0019100000-4a0326cc696d703a5ddf2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, negativesplash10-004j-0049000000-644404aebf53ce6e384b2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, negativesplash10-002b-0195000000-bf383e9b2a31869a32502020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF 10V, negativesplash10-0002-0000900000-8e6d30577df9f5fc94df2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF 20V, negativesplash10-0002-0014900000-de11af075e5b872f5b322020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF 30V, negativesplash10-002b-0069300000-4170d340b65f08002cea2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF 40V, negativesplash10-0002-0093000000-c28146f9492cb714d0df2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF 50V, negativesplash10-00kb-0090000000-9f29188d1544babad8792020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 30V, negativesplash10-056r-0019100000-d6b0da8ace5fdd2b031e2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 44V, negativesplash10-056r-0009000000-e5d6e7c2132bc002d50e2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-0002-0001900000-46da78235af928d5dccf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-002b-0006900000-e6b4f4be3a0997ba53202020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 19V, negativesplash10-004i-0009200000-dcb8b76dcdf09cb2e5aa2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 23V, negativesplash10-004i-0009000000-c3b29afef929063428092020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 27V, negativesplash10-004i-0019000000-ebed207e06f9c3a67f312020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 35V, negativesplash10-004j-0059000000-7fc0ebcbd4516ac8f9482020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 43V, negativesplash10-002b-0393000000-88e23ef9f43b11b04d752020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 51V, negativesplash10-000t-0890000000-4e953bf64944a769933d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 60V, negativesplash10-001i-0940000000-a7394e90fc9580d2bf232020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 68V, negativesplash10-001i-1920000000-726c227d6590b8e5dbec2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 75V, negativesplash10-001i-1910000000-871a3e19a0ba47eab4df2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 87V, negativesplash10-001i-2900000000-c3700a5bfe4adc3d16dd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 99V, negativesplash10-001i-3900000000-ed917324674cd78691a72020-07-22View 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 IDNot Available
KNApSAcK IDC00001078
Chemspider IDNot Available
KEGG Compound IDC10114
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOrientin
METLIN IDNot Available
PubChem Compound5281675
PDB IDNot Available
ChEBI ID7781
References
General References
  1. 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 ]
  2. Lam KY, Ling AP, Koh RY, Wong YP, Say YH: A Review on Medicinal Properties of Orientin. Adv Pharmacol Sci. 2016;2016:4104595. doi: 10.1155/2016/4104595. Epub 2016 May 19. [PubMed:27298620 ]