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Showing NP-Card for trans-p-Coumaric acid 4-[apiosyl-(1->2)-glucoside] (NP0335373)

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Record Information
Version2.0
Created at2024-09-11 01:18:22 UTC
Updated at2024-09-11 01:18:22 UTC
NP-MRD IDNP0335373
Secondary Accession NumbersNone
Natural Product Identification
Common Nametrans-p-Coumaric acid 4-[apiosyl-(1->2)-glucoside]
DescriptionCis-p-Coumaric acid 4-[apiosyl-(1->2)-glucoside] belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Based on a literature review very few articles have been published on cis-p-Coumaric acid 4-[apiosyl-(1->2)-glucoside].
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0335373 (trans-p-Coumaric acid 4-[apiosyl-(1->2)-glucoside])


  Mrv2104 05262303502D          

 32 34  0  0  0  0            999 V2000
    0.1068   -0.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122    0.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2561    0.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4423   -1.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7477   -0.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7411    1.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9105   -3.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9136    1.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1331    0.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5917    0.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2628   -1.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5749   -3.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4055    2.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0598   -2.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7243   -1.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038   -1.5148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7982    0.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4189   -2.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0531   -0.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4255   -4.4432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1066    1.6175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4150    2.4261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904    3.0073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8803   -2.4409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2092   -0.9336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0136    0.9459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0177    1.7890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8781   -0.0937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5984   -2.0960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7544   -2.9359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5682   -0.7611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  3  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  6  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  8  1  0  0  0  0
 20  9  1  0  0  0  0
 20 17  1  0  0  0  0
 21  7  1  0  0  0  0
 22  8  1  0  0  0  0
 23 13  2  0  0  0  0
 24 13  1  0  0  0  0
 25 14  1  0  0  0  0
 26 15  1  0  0  0  0
 27 17  1  0  0  0  0
 28 20  1  0  0  0  0
 29  9  1  0  0  0  0
 29 19  1  0  0  0  0
 30 11  1  0  0  0  0
 30 18  1  0  0  0  0
 31 12  1  0  0  0  0
 31 18  1  0  0  0  0
 32 16  1  0  0  0  0
 32 19  1  0  0  0  0
M  END
Download

3D MOL for NP0335373 (trans-p-Coumaric acid 4-[apiosyl-(1->2)-glucoside])

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3D SDF for NP0335373 (trans-p-Coumaric acid 4-[apiosyl-(1->2)-glucoside])

  Mrv2104 05262303502D          

 32 34  0  0  0  0            999 V2000
    0.1068   -0.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122    0.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2561    0.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4423   -1.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7477   -0.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7411    1.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9105   -3.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9136    1.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1331    0.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5917    0.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2628   -1.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5749   -3.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4055    2.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0598   -2.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7243   -1.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038   -1.5148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7982    0.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4189   -2.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0531   -0.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4255   -4.4432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1066    1.6175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4150    2.4261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904    3.0073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8803   -2.4409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2092   -0.9336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0136    0.9459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0177    1.7890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8781   -0.0937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5984   -2.0960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7544   -2.9359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5682   -0.7611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  3  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  6  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  8  1  0  0  0  0
 20  9  1  0  0  0  0
 20 17  1  0  0  0  0
 21  7  1  0  0  0  0
 22  8  1  0  0  0  0
 23 13  2  0  0  0  0
 24 13  1  0  0  0  0
 25 14  1  0  0  0  0
 26 15  1  0  0  0  0
 27 17  1  0  0  0  0
 28 20  1  0  0  0  0
 29  9  1  0  0  0  0
 29 19  1  0  0  0  0
 30 11  1  0  0  0  0
 30 18  1  0  0  0  0
 31 12  1  0  0  0  0
 31 18  1  0  0  0  0
 32 16  1  0  0  0  0
 32 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335373

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=CC=C(\C=C\C(O)=O)C=C2)C(OC2OCC(O)(CO)C2O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1/C20H26O12/c21-7-12-14(25)15(26)16(32-19-17(27)20(28,8-22)9-29-19)18(31-12)30-11-4-1-10(2-5-11)3-6-13(23)24/h1-6,12,14-19,21-22,25-28H,7-9H2,(H,23,24)/b6-3+

> <INCHI_KEY>
DAVWDWCHQLSZAZ-ZZXKWVIFNA-N

> <FORMULA>
C20H26O12

> <MOLECULAR_WEIGHT>
458.416

> <EXACT_MASS>
458.142426277

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
44.85756039198462

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}prop-2-enoic acid

> <JCHEM_LOGP>
-1.7120462149999995

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.807562257375947

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.531346219642018

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810925692672834

> <JCHEM_POLAR_SURFACE_AREA>
195.59999999999997

> <JCHEM_REFRACTIVITY>
103.8554

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0335373 (trans-p-Coumaric acid 4-[apiosyl-(1->2)-glucoside])
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PDB for NP0335373 (trans-p-Coumaric acid 4-[apiosyl-(1->2)-glucoside])
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       0.199  -0.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.636   0.147   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.478   1.715   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.826  -2.345   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.262  -1.260   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.383   2.961   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.300  -7.048   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.439   3.339   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.715   1.290   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.105   0.308   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.357  -2.506   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.673  -5.641   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.757   4.368   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.578  -4.395   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.952  -2.989   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.420  -2.828   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.223   1.290   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.515  -4.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.699  -0.175   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.394  -8.294   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.932   3.019   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.775   4.529   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.662   5.614   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.110  -4.556   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.857  -1.743   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       3.759   1.766   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       7.500   3.339   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       7.239  -0.175   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.984  -3.913   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.142  -5.480   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       4.794  -1.421   0.000  0.00  0.00           O+0
CONECT    1    4   10                                                       
CONECT    2    5   10                                                       
CONECT    3    6   10                                                       
CONECT    4    1   11                                                       
CONECT    5    2   11                                                       
CONECT    6    3   13                                                       
CONECT    7   12   21                                                       
CONECT    8   20   22                                                       
CONECT    9   20   29                                                       
CONECT   10    1    2    3                                                  
CONECT   11    4    5   30                                                  
CONECT   12    7   14   31                                                  
CONECT   13    6   23   24                                                  
CONECT   14   12   15   25                                                  
CONECT   15   14   16   26                                                  
CONECT   16   15   18   32                                                  
CONECT   17   19   20   27                                                  
CONECT   18   16   30   31                                                  
CONECT   19   17   29   32                                                  
CONECT   20    8    9   17   28                                             
CONECT   21    7                                                            
CONECT   22    8                                                            
CONECT   23   13                                                            
CONECT   24   13                                                            
CONECT   25   14                                                            
CONECT   26   15                                                            
CONECT   27   17                                                            
CONECT   28   20                                                            
CONECT   29    9   19                                                       
CONECT   30   11   18                                                       
CONECT   31   12   18                                                       
CONECT   32   16   19                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

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3D PDB for NP0335373 (trans-p-Coumaric acid 4-[apiosyl-(1->2)-glucoside])
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SMILES for NP0335373 (trans-p-Coumaric acid 4-[apiosyl-(1->2)-glucoside])
OCC1OC(OC2=CC=C(\C=C\C(O)=O)C=C2)C(OC2OCC(O)(CO)C2O)C(O)C1O
Download
INCHI for NP0335373 (trans-p-Coumaric acid 4-[apiosyl-(1->2)-glucoside])
InChI=1/C20H26O12/c21-7-12-14(25)15(26)16(32-19-17(27)20(28,8-22)9-29-19)18(31-12)30-11-4-1-10(2-5-11)3-6-13(23)24/h1-6,12,14-19,21-22,25-28H,7-9H2,(H,23,24)/b6-3+
Download
View in JSmol
Synonyms
ValueSource
cis-p-Coumarate 4-[apiosyl-(1->2)-glucoside]Generator
Chemical FormulaC20H26O12
Average Mass458.4160 Da
Monoisotopic Mass458.14243 Da
IUPAC Name(2E)-3-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}prop-2-enoic acid
Traditional Name(2E)-3-{4-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]phenyl}prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
OCC1OC(OC2=CC=C(\C=C\C(O)=O)C=C2)C(OC2OCC(O)(CO)C2O)C(O)C1O
InChI Identifier
InChI=1/C20H26O12/c21-7-12-14(25)15(26)16(32-19-17(27)20(28,8-22)9-29-19)18(31-12)30-11-4-1-10(2-5-11)3-6-13(23)24/h1-6,12,14-19,21-22,25-28H,7-9H2,(H,23,24)/b6-3+
InChI KeyDAVWDWCHQLSZAZ-ZZXKWVIFNA-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 phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentPhenolic glycosides  
Alternative Parents
Substituents
  • Phenolic glycoside
    • 

  • Cinnamic acid
    • 

  • Cinnamic acid or derivatives
    • 

  • Disaccharide
    • 

  • O-glycosyl compound
    • 

  • Phenoxy compound
    • 

  • Phenol ether
    • 

  • Styrene
    • 

  • Monocyclic benzene moiety
    • 

  • Oxane
    • 

  • Benzenoid
    • 

  • Tetrahydrofuran
    • 

  • Tertiary alcohol
    • 

  • Secondary alcohol
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Oxacycle
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Acetal
    • 

  • Primary alcohol
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP-1.7ChemAxon
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area195.6 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity103.86 m³·mol⁻¹ChemAxon
Polarizability44.86 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