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Record Information
Version1.0
Created at2021-11-12 23:44:20 UTC
Updated at2021-11-26 17:44:41 UTC
NP-MRD IDNP0044035
Secondary Accession NumbersNone
Natural Product Identification
Common NameRobustaside A
DescriptionCinnamoylglycine belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Cinnamoylglycine is an extremely weak basic (essentially neutral) compound (based on its pKa). Robustaside A is found in Breynia officinalis, Breynia vitis-idaea, Grevillea robusta, Grevillea robusta A.Cunn, Vaccinium arctostaphylos and Viburnum wrightii. It was first documented in 2000 (PMID: 10656423). An N-acylglycine in which the acyl group is specified as (2E)-3-phenylprop-2-enoyl (cinnamoyl) (PMID: 34748561) (PMID: 34746809) (PMID: 34740265) (PMID: 34728144).
Structure
Thumb
Synonyms
ValueSource
N-(1-oxo-3-Phenyl-2-propenyl)-glycineChEBI
N-CinnamylglycineChEBI
N-(1-oxo-3-Phenyl-2-propen-1-yl)-glycineHMDB
N-Cinnamoyl-glycineHMDB
N-CinnamoylglycineHMDB
CinnamoylglycineMeSH
Chemical FormulaC21H22O9
Average Mass418.3980 Da
Monoisotopic Mass418.12638 Da
IUPAC Name2-[(2E)-3-phenylprop-2-enamido]acetic acid
Traditional Name[(2E)-3-phenylprop-2-enamido]acetic acid
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=CC=C(O)C=C2)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C21H22O9/c22-13-4-1-12(2-5-13)3-10-17(24)28-11-16-18(25)19(26)20(27)21(30-16)29-15-8-6-14(23)7-9-15/h1-10,16,18-23,25-27H,11H2/b10-3+/t16-,18-,19+,20-,21-/m1/s1
InChI KeyDTBYJDROKVCOQC-CEKNMCGLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Breynia officinalisPlant
Breynia vitis-idaeaLOTUS Database
Grevillea robustaLOTUS Database
Grevillea robusta A.CunnPlant
Vaccinium arctostaphylosLOTUS Database
Viburnum wrightiiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Cinnamic acid amide
  • Cinnamic acid or derivatives
  • Styrene
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP1.42ALOGPS
logP1.03ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)3.9ChemAxon
pKa (Strongest Basic)-0.71ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.86 m³·mol⁻¹ChemAxon
Polarizability21.16 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0011621
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028325
KNApSAcK IDNot Available
Chemspider ID618829
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound709625
PDB IDNot Available
ChEBI ID68616
Good Scents IDNot Available
References
General References
  1. Ahmed AS, Nakamura N, Meselhy MR, Makhboul MA, El-Emary N, Hattori M: Phenolic constituents from Grevillea robusta. Phytochemistry. 2000 Jan;53(1):149-54. doi: 10.1016/s0031-9422(99)00484-7. [PubMed:10656423 ]
  2. Rai A, Chettri M, Dewan S, Khandelwal B, Chettri B: Epidemiological study of snakebite cases in Sikkim: Risk modeling with regard to the habitat suitability of common venomous snakes. PLoS Negl Trop Dis. 2021 Nov 8;15(11):e0009800. doi: 10.1371/journal.pntd.0009800. eCollection 2021 Nov. [PubMed:34748561 ]
  3. Parihar PS, Singh A, Karade SS, Sahasrabuddhe AA, Pratap JV: Structural insights into kinetoplastid coronin oligomerization domain and F-actin interaction. Curr Res Struct Biol. 2021 Oct 14;3:268-276. doi: 10.1016/j.crstbi.2021.10.002. eCollection 2021. [PubMed:34746809 ]
  4. Sanjeev MN, Kaur H, Mayall SS, Rishika, Yeluri R: Resorbable Collagen Barrier Impeding the Extrusion of Obturating Material in Primary Molars Undergoing Resorption - A Randomized Clinical Trial. J Clin Pediatr Dent. 2021 Nov 1;45(5):312-316. doi: 10.17796/1053-4625-45.5.4. [PubMed:34740265 ]
  5. Bechara R, Gaffen SL: '(m(6))A' stands for 'autoimmunity': reading, writing, and erasing RNA modifications during inflammation. Trends Immunol. 2021 Oct 30. pii: S1471-4906(21)00207-6. doi: 10.1016/j.it.2021.10.002. [PubMed:34728144 ]