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Record Information
Version1.0
Created at2021-11-12 23:56:44 UTC
Updated at2021-11-26 17:46:34 UTC
NP-MRD IDNP0044201
Secondary Accession NumbersNone
Natural Product Identification
Common NameCalceolarioside A
DescriptionCalceolarioside A 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. Calceolarioside A is found in Aeschynanthus bracteatus , Ajuga nipponensis, Avicennia marina, Buddleja officinalis, Byblis liniflora, Calceolaria dentata, Calceolaria hypericina, Cassinopsis madagascariensis, Digitalis purpurea, Digitalis thapsi , Echinacea pallida, Ellisiophyllum pinnatum (Wall.ex.Benth.), Forsythia suspensa, Fraxinus insularis, Globularia alypum, Globularia orientalis, Isoplexis sceptrum, Lantana strigocamara, Meehania urticifolia, Nyctanthes arbor-tristis, Phlomoides hamosa, Plantago lanceolata, Plantago major and Primulina sinensis. It was first documented in 2017 (PMID: 30549826). Based on a literature review a significant number of articles have been published on Calceolarioside A (PMID: 32247053) (PMID: 34498959) (PMID: 30676780) (PMID: 27533742).
Structure
Thumb
Synonyms
ValueSource
CalceolariosideMeSH
Chemical FormulaC23H26O11
Average Mass478.4500 Da
Monoisotopic Mass478.14751 Da
IUPAC Name(2R,3S,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Traditional Name(2R,3S,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](OCCC2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C23H26O11/c24-11-18-22(34-19(29)6-3-12-1-4-14(25)16(27)9-12)20(30)21(31)23(33-18)32-8-7-13-2-5-15(26)17(28)10-13/h1-6,9-10,18,20-28,30-31H,7-8,11H2/b6-3+/t18-,20-,21-,22-,23-/m1/s1
InChI KeyUHIGZYLCYRQESL-VJWFJHQPSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aeschynanthus bracteatusPlant
Ajuga nipponensisLOTUS Database
Avicennia marinaLOTUS Database
Buddleja officinalisLOTUS Database
Byblis linifloraLOTUS Database
Calceolaria dentataLOTUS Database
Calceolaria hypericinaPlant
Cassinopsis madagascariensisLOTUS Database
Digitalis purpureaLOTUS Database
Digitalis thapsiPlant
Echinacea pallidaLOTUS Database
Ellisiophyllum pinnatum (Wall.ex.Benth.)Plant
Forsythia suspensaLOTUS Database
Fraxinus insularisLOTUS Database
Globularia alypumLOTUS Database
Globularia orientalisLOTUS Database
Isoplexis sceptrumPlant
Lantana strigocamaraLOTUS Database
Meehania urticifoliaLOTUS Database
Nyctanthes arbor-tristisLOTUS Database
Phlomoides hamosaLOTUS Database
Plantago lanceolataLOTUS Database
Plantago majorLOTUS Database
Primulina sinensisLOTUS 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
  • Hexose monosaccharide
  • Cinnamic acid ester
  • 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
  • Monosaccharide
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP0.81ALOGPS
logP1.54ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.01ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity117.53 m³·mol⁻¹ChemAxon
Polarizability47.58 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00033685
Chemspider ID4437969
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5273566
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Morikawa T, Inoue N, Nakanishi Y, Manse Y, Matsuura H, Okino K, Hamasaki S, Yoshikawa M, Muraoka O, Ninomiya K: Collagen synthesis-promoting and collagenase inhibitory activities of constituents isolated from the rhizomes of Picrorhiza kurroa Royle ex Benth. Fitoterapia. 2020 Jun;143:104584. doi: 10.1016/j.fitote.2020.104584. Epub 2020 Apr 1. [PubMed:32247053 ]
  2. Winiewski V, Mesquita Fonseca M, Salvador MJ, Lemos de Sa E, Alves Stefanello ME: Three new naphthoquinones from the tubers of Sinningia mauroana. Nat Prod Res. 2021 Sep 9:1-6. doi: 10.1080/14786419.2021.1969564. [PubMed:34498959 ]
  3. Wei Q, Zhang R, Wang Q, Yan XJ, Yu QW, Yan FX, Li C, Pei YH: Iridoid, phenylethanoid and flavonoid glycosides from Forsythia suspensa. Nat Prod Res. 2020 May;34(9):1320-1325. doi: 10.1080/14786419.2018.1560288. Epub 2019 Jan 24. [PubMed:30676780 ]
  4. Kirmizibekmez H, Kusz N, Karaca N, Demirci F, Hohmann' J: Secondary Metabolites from the Leaves of Digitalis viridiflora. Nat Prod Commun. 2017 Jan;12(1):59-61. [PubMed:30549826 ]
  5. Chen Y, Xue G, Liu F, Gong X: Immunosuppressive effect of extracts from leaves of Fraxinus Mandshurica Rupr. Bioengineered. 2017 May 4;8(3):212-216. doi: 10.1080/21655979.2016.1221023. Epub 2016 Aug 17. [PubMed:27533742 ]
  6. Søren Damtoft and Søren Rosendal Jensen (1994). Three phenylethanoid glucosides of unusual structure from Chirita sinensis (gesneriaceae). Phytochemistry, Volume 37, Issue 2, 1994, Pages 441-443. DOI: Volume 37, Issue 2, 1994, Pages 441-443. Phytochemistry.