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Showing NP-Card for Robustaside A (NP0044035)

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Record Information
Version2.0
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. An N-acylglycine in which the acyl group is specified as (2E)-3-phenylprop-2-enoyl (cinnamoyl).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0044035 (Robustaside A)


  Mrv1652309121709222D          

 15 15  0  0  0  0            999 V2000
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
Download

3D MOL for NP0044035 (Robustaside A)

     RDKit          3D

 26 26  0  0  0  0  0  0  0  0999 V2000
    4.3799    1.4181   -1.0242 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8129    0.3678   -0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1496    0.0001   -0.5850 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8505   -0.4659    0.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6475    0.0959    0.5475 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4239    0.6695    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2190    1.7679    1.3487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1651    0.0170    0.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9658    0.6307    0.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2605    0.1019    0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4465   -1.1588   -0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6931   -1.5963   -0.8749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7716   -0.7695   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6200    0.4962   -0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3736    0.9227    0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7446    0.3807    0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3967   -0.8484    1.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7266   -1.4230   -0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417    1.1552    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2268   -0.9696   -0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9492    1.6108    0.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5646   -1.8079   -0.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8098   -2.5892   -1.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7762   -1.0840   -1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4893    1.1713   -0.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2645    1.9066    0.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10 15  1  0
 15 14  2  0
 10  9  1  0
  9  8  2  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  2  0
  2  3  1  0
 14 13  1  0
 13 24  1  0
 12 23  1  0
 11 22  1  0
 15 26  1  0
 14 25  1  0
  9 21  1  0
  8 20  1  0
  5 19  1  0
  4 17  1  0
  4 18  1  0
  3 16  1  0
M  END
Download

3D SDF for NP0044035 (Robustaside A)


  Mrv1652309121709222D          

 15 15  0  0  0  0            999 V2000
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044035

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CNC(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H11NO3/c13-10(12-8-11(14)15)7-6-9-4-2-1-3-5-9/h1-7H,8H2,(H,12,13)(H,14,15)/b7-6+

> <INCHI_KEY>
YAADMLWHGMUGQL-VOTSOKGWSA-N

> <FORMULA>
C11H11NO3

> <MOLECULAR_WEIGHT>
205.2099

> <EXACT_MASS>
205.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.164321766371767

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2E)-3-phenylprop-2-enamido]acetic acid

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.030803020333333

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.718884571874998

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9010068308625008

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7101446007294613

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
55.8634

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2E)-3-phenylprop-2-enamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0044035 (Robustaside A)

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PDB for NP0044035 (Robustaside A)
HEADER    PROTEIN                                 12-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-17         0                                  
HETATM    1  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       4.001   6.930   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002   7.700   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.668   5.390   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

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3D PDB for NP0044035 (Robustaside A)
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SMILES for NP0044035 (Robustaside A)
OC(=O)CNC(=O)\C=C\C1=CC=CC=C1
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INCHI for NP0044035 (Robustaside A)
InChI=1S/C11H11NO3/c13-10(12-8-11(14)15)7-6-9-4-2-1-3-5-9/h1-7H,8H2,(H,12,13)(H,14,15)/b7-6+
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View in JSmol
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