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Showing NP-Card for trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester (NP0336205)

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Record Information
Version2.0
Created at2024-09-11 05:12:14 UTC
Updated at2024-09-11 05:12:15 UTC
NP-MRD IDNP0336205
Secondary Accession NumbersNone
Natural Product Identification
Common Nametrans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester
DescriptionTrans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives. Based on a literature review very few articles have been published on trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336205 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)


  Mrv2104 05262307442D          

 33 35  0  0  0  0            999 V2000
   -3.6810  -10.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5316   -8.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3454  -11.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0467   -8.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3756   -9.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5986   -3.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5887   -0.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1960   -9.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3822   -7.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9040   -4.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3889   -5.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533   -5.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4492   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3957   -0.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7479   -5.4109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8973   -6.8320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
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  9  2  1  0  0  0  0
  9  5  2  0  0  0  0
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 32 12  1  0  0  0  0
 32 18  1  0  0  0  0
 33 13  1  0  0  0  0
 33 18  1  0  0  0  0
M  END
Download

3D MOL for NP0336205 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)

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3D SDF for NP0336205 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)

  Mrv2104 05262307442D          

 33 35  0  0  0  0            999 V2000
   -3.6810  -10.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5316   -8.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3454  -11.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0467   -8.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3756   -9.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5986   -3.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5887   -0.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1960   -9.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5249  -11.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0400  -10.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0835   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3822   -7.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9040   -4.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3889   -5.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533   -5.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2329   -6.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3957   -0.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1894  -11.9352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2195  -10.6004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2027   -7.4132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2395   -3.8173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2094   -5.1522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5383   -6.6595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4888   -1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4847   -0.6860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9341   -3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7479   -5.4109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8973   -6.8320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  5  2  0  0  0  0
 10  3  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12  6  1  0  0  0  0
 13  4  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20  7  1  0  0  0  0
 20  8  1  0  0  0  0
 20 17  1  0  0  0  0
 21  7  1  0  0  0  0
 22 10  1  0  0  0  0
 23 11  1  0  0  0  0
 24 13  2  0  0  0  0
 25 14  1  0  0  0  0
 26 15  1  0  0  0  0
 27 16  1  0  0  0  0
 28 17  1  0  0  0  0
 29 20  1  0  0  0  0
 30  6  1  0  0  0  0
 30 19  1  0  0  0  0
 31  8  1  0  0  0  0
 31 19  1  0  0  0  0
 32 12  1  0  0  0  0
 32 18  1  0  0  0  0
 33 13  1  0  0  0  0
 33 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336205

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1(O)COC(OCC2OC(OC(=O)\C=C\C3=CC(O)=C(O)C=C3)C(O)C(O)C2O)C1O

> <INCHI_IDENTIFIER>
InChI=1/C20H26O13/c21-7-20(29)8-31-19(17(20)28)30-6-12-14(25)15(26)16(27)18(32-12)33-13(24)4-2-9-1-3-10(22)11(23)5-9/h1-5,12,14-19,21-23,25-29H,6-8H2/b4-2+

> <INCHI_KEY>
LULOGYYPGZOKQW-DUXPYHPUNA-N

> <FORMULA>
C20H26O13

> <MOLECULAR_WEIGHT>
474.415

> <EXACT_MASS>
474.137340897

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
46.101075556842716

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
-1.7822782033333322

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.651246977224007

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.207041366432335

> <JCHEM_PKA_STRONGEST_BASIC>
-3.142379016338922

> <JCHEM_POLAR_SURFACE_AREA>
215.82999999999993

> <JCHEM_REFRACTIVITY>
106.12309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0336205 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)
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PDB for NP0336205 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -6.871 -19.305   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.592 -16.652   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.245 -20.711   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.687 -15.406   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.434 -18.220   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.851  -7.448   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.832  -1.281   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.556  -3.330   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.966 -18.059   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.713 -20.872   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.808 -19.626   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.756  -8.693   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.313 -13.999   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -7.287  -8.533   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.193  -9.778   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.566 -11.185   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.048  -3.330   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.035 -11.346   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.572  -4.795   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.802  -2.425   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.339  -1.601   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.087 -22.279   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.276 -19.787   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -7.845 -13.838   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -7.914  -7.126   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -9.724  -9.617   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -8.471 -12.431   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -6.512  -2.854   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -2.771  -1.281   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -5.477  -6.041   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -3.032  -4.795   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -5.129 -10.100   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -5.408 -12.753   0.000  0.00  0.00           O+0
CONECT    1    3    9                                                       
CONECT    2    4    9                                                       
CONECT    3    1   10                                                       
CONECT    4    2   13                                                       
CONECT    5    9   11                                                       
CONECT    6   12   30                                                       
CONECT    7   20   21                                                       
CONECT    8   20   31                                                       
CONECT    9    1    2    5                                                  
CONECT   10    3   11   22                                                  
CONECT   11    5   10   23                                                  
CONECT   12    6   14   32                                                  
CONECT   13    4   24   33                                                  
CONECT   14   12   15   25                                                  
CONECT   15   14   16   26                                                  
CONECT   16   15   18   27                                                  
CONECT   17   19   20   28                                                  
CONECT   18   16   32   33                                                  
CONECT   19   17   30   31                                                  
CONECT   20    7    8   17   29                                             
CONECT   21    7                                                            
CONECT   22   10                                                            
CONECT   23   11                                                            
CONECT   24   13                                                            
CONECT   25   14                                                            
CONECT   26   15                                                            
CONECT   27   16                                                            
CONECT   28   17                                                            
CONECT   29   20                                                            
CONECT   30    6   19                                                       
CONECT   31    8   19                                                       
CONECT   32   12   18                                                       
CONECT   33   13   18                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

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3D PDB for NP0336205 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)
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SMILES for NP0336205 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)
OCC1(O)COC(OCC2OC(OC(=O)\C=C\C3=CC(O)=C(O)C=C3)C(O)C(O)C2O)C1O
Download
INCHI for NP0336205 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)
InChI=1/C20H26O13/c21-7-20(29)8-31-19(17(20)28)30-6-12-14(25)15(26)16(27)18(32-12)33-13(24)4-2-9-1-3-10(22)11(23)5-9/h1-5,12,14-19,21-23,25-29H,6-8H2/b4-2+
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View in JSmol
Synonyms
ValueSource
trans-Caffeate [apiosyl-(1->6)-glucosyl] esterGenerator
Chemical FormulaC20H26O13
Average Mass474.4150 Da
Monoisotopic Mass474.13734 Da
IUPAC Name6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Traditional Name6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
CAS Registry NumberNot Available
SMILES
OCC1(O)COC(OCC2OC(OC(=O)\C=C\C3=CC(O)=C(O)C=C3)C(O)C(O)C2O)C1O
InChI Identifier
InChI=1/C20H26O13/c21-7-20(29)8-31-19(17(20)28)30-6-12-14(25)15(26)16(27)18(32-12)33-13(24)4-2-9-1-3-10(22)11(23)5-9/h1-5,12,14-19,21-23,25-29H,6-8H2/b4-2+
InChI KeyLULOGYYPGZOKQW-DUXPYHPUNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamic acids and derivatives  
Sub ClassHydroxycinnamic acids and derivatives  
Direct ParentHydroxycinnamic acid glycosides  
Alternative Parents
Substituents
  • Hydroxycinnamic acid glycoside
    • 

  • O-cinnamoyl glycoside
    • 

  • Cinnamic acid ester
    • 

  • Coumaric acid or derivatives
    • 

  • Disaccharide
    • 

  • Glycosyl compound
    • 

  • O-glycosyl compound
    • 

  • Styrene
    • 

  • Catechol
    • 

  • Fatty acid ester
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Fatty acyl
    • 

  • Benzenoid
    • 

  • Oxane
    • 

  • Monocyclic benzene moiety
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Tetrahydrofuran
    • 

  • Tertiary alcohol
    • 

  • Carboxylic acid ester
    • 

  • Secondary alcohol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Acetal
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Polyol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Primary alcohol
    • 

  • 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
logP-1.8ChemAxon
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area215.83 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity106.12 m³·mol⁻¹ChemAxon
Polarizability46.1 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available