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Record Information
Version2.0
Created at2022-09-08 10:35:59 UTC
Updated at2022-09-08 10:35:59 UTC
NP-MRD IDNP0266297
Secondary Accession NumbersNone
Natural Product Identification
Common Namelucenin-2
DescriptionLucenin-2 belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Lucenin-2 is an extremely weak basic (essentially neutral) compound (based on its pKa). lucenin-2 is found in Artemisia herba-alba, Artemisia monosperma, Carlina corymbosa, Cydonia oblonga, Parkinsonia aculeata and Passiflora incarnata. lucenin-2 was first documented in 1992 (PMID: 1484895). A C-glycosyl compound that is luteolin substituted by beta-D-glucopyranosyl moieties at positions 6 and 8 respectively (PMID: 12591270) (PMID: 14667061) (PMID: 20184017) (PMID: 21111038).
Structure
Thumb
Synonyms
ValueSource
Luteolin 6,8-di-C-glucosideChEBI
Chemical FormulaC27H30O16
Average Mass610.5210 Da
Monoisotopic Mass610.15338 Da
IUPAC Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-bis[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
Traditional Namelucenin-2
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C2=C(OC(=CC2=O)C2=CC=C(O)C(O)=C2)C([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1O
InChI Identifier
InChI=1S/C27H30O16/c28-5-12-17(33)21(37)23(39)26(42-12)15-19(35)14-10(32)4-11(7-1-2-8(30)9(31)3-7)41-25(14)16(20(15)36)27-24(40)22(38)18(34)13(6-29)43-27/h1-4,12-13,17-18,21-24,26-31,33-40H,5-6H2/t12-,13-,17-,18-,21+,22+,23-,24-,26+,27+/m1/s1
InChI KeyZLPSOQFIIQIIAX-VQVVXJKKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artemisia herba-albaLOTUS Database
Artemisia monospermaLOTUS Database
Carlina corymbosaLOTUS Database
Cydonia oblongaLOTUS Database
Parkinsonia aculeataLOTUS Database
Passiflora incarnataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid C-glycosides
Alternative Parents
Substituents
  • Flavonoid c-glycoside
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • Chromone
  • C-glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Primary alcohol
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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-0.97ALOGPS
logP-3.1ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)5.74ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area287.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity141.13 m³·mol⁻¹ChemAxon
Polarizability58.05 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00006231
Chemspider IDNot Available
KEGG Compound IDC10102
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442615
PDB IDNot Available
ChEBI ID6553
Good Scents IDNot Available
References
General References
  1. Hoffmann-Bohm K, Lotter H, Seligmann O, Wagner H: Antihepatotoxic C-glycosylflavones from the leaves of Allophyllus edulis var. edulis and gracilis. Planta Med. 1992 Dec;58(6):544-8. doi: 10.1055/s-2006-961546. [PubMed:1484895 ]
  2. Basile A, Sorbo S, Lopez-Saez JA, Castaldo Cobianchi R: Effects of seven pure flavonoids from mosses on germination and growth of Tortula muralis HEDW (Bryophyta) and Raphanus sativus L (Magnoliophyta). Phytochemistry. 2003 Apr;62(7):1145-51. doi: 10.1016/s0031-9422(02)00659-3. [PubMed:12591270 ]
  3. Ferreres F, Silva BM, Andrade PB, Seabra RM, Ferreira MA: Approach to the study of C-glycosyl flavones by ion trap HPLC-PAD-ESI/MS/MS: application to seeds of quince (Cydonia oblonga). Phytochem Anal. 2003 Nov-Dec;14(6):352-9. doi: 10.1002/pca.727. [PubMed:14667061 ]
  4. Iwashina T, Matsumoto S, Kitajima J, Nakamura T, Kokubugata G, Suleiman M, Said IM: Apigenin di- and trirhamnoside from Asplenium normale in Malaysia. Nat Prod Commun. 2010 Jan;5(1):39-42. [PubMed:20184017 ]
  5. Li H, Zhou P, Yang Q, Shen Y, Deng J, Li L, Zhao D: Comparative studies on anxiolytic activities and flavonoid compositions of Passiflora edulis 'edulis' and Passiflora edulis 'flavicarpa'. J Ethnopharmacol. 2011 Feb 16;133(3):1085-90. doi: 10.1016/j.jep.2010.11.039. Epub 2010 Nov 24. [PubMed:21111038 ]
  6. LOTUS database [Link]