NP-MRD: Showing NP-Card for Pelargonidin 3-(6''-caffeylglucoside) (NP0054515)

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Record Information

Version

2.0

Created at

2022-04-28 00:50:44 UTC

Updated at

2022-04-28 00:50:44 UTC

NP-MRD ID

NP0054515

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pelargonidin 3-(6''-caffeylglucoside)

Description

Pelargonidin 3-(6''-caffeylglucoside) is found in Ipomoea nil .

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202502D          

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M  CHG  1   7   1
M  END

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M  END


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    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    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
  5  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
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 28 30  1  0  0  0  0
 27 31  1  0  0  0  0
 15 32  1  6  0  0  0
 14 33  1  6  0  0  0
 13 34  1  1  0  0  0
  8 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 40  1  0  0  0  0
 38 41  1  0  0  0  0
  3 42  1  0  0  0  0
  1 43  1  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
NP0054515

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@H](COC(=O)\C=C\C2=CC=C(O)C(O)=C2)O[C@@H](OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC=C(O)C=C2)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O13/c31-16-5-3-15(4-6-16)29-23(12-18-20(34)10-17(32)11-22(18)41-29)42-30-28(39)27(38)26(37)24(43-30)13-40-25(36)8-2-14-1-7-19(33)21(35)9-14/h1-12,24,26-28,30,37-39H,13H2,(H4-,31,32,33,34,35,36)/p+1/t24-,26+,27+,28-,30+/m0/s1

> <INCHI_KEY>
OUWGZZOPFVOIFO-XZDDPZDKSA-O

> <FORMULA>
C30H27O13

> <MOLECULAR_WEIGHT>
595.532

> <EXACT_MASS>
595.14461735

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
57.16945828598356

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2S,3S,4R,5S,6S)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)-1lambda4-chromen-1-ylium

> <ALOGPS_LOGP>
3.21

> <JCHEM_LOGP>
3.800699999999999

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.527393643546798

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.396149062104928

> <JCHEM_PKA_STRONGEST_BASIC>
-3.64911035489539

> <JCHEM_POLAR_SURFACE_AREA>
219.73999999999995

> <JCHEM_REFRACTIVITY>
157.8061

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3S,4R,5S,6S)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)-1lambda4-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+1
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.000 -16.940   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.667 -18.480   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   43                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   42                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   35                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   34                                                  
CONECT   14   13   15   33                                                  
CONECT   15   14   16   32                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   24                                                       
CONECT   30   28                                                            
CONECT   31   27                                                            
CONECT   32   15                                                            
CONECT   33   14                                                            
CONECT   34   13                                                            
CONECT   35    8   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39   35                                                       
CONECT   41   38                                                            
CONECT   42    3                                                            
CONECT   43    1                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₇O₁₃

Average Mass

595.5320 Da

Monoisotopic Mass

595.14462 Da

IUPAC Name

3-{[(2S,3S,4R,5S,6S)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)-1lambda4-chromen-1-ylium

Traditional Name

3-{[(2S,3S,4R,5S,6S)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)-1lambda4-chromen-1-ylium

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@H](COC(=O)\C=C\C2=CC=C(O)C(O)=C2)O[C@@H](OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC=C(O)C=C2)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C30H26O13/c31-16-5-3-15(4-6-16)29-23(12-18-20(34)10-17(32)11-22(18)41-29)42-30-28(39)27(38)26(37)24(43-30)13-40-25(36)8-2-14-1-7-19(33)21(35)9-14/h1-12,24,26-28,30,37-39H,13H2,(H4-,31,32,33,34,35,36)/p+1/t24-,26+,27+,28-,30+/m0/s1

InChI Key

OUWGZZOPFVOIFO-XZDDPZDKSA-O

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ipomoea nil	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.21	ALOGPS
logP	3.8	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	6.4	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	219.74 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	157.81 m³·mol⁻¹	ChemAxon
Polarizability	57.17 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for Pelargonidin 3-(6''-caffeylglucoside) (NP0054515)

MOL for NP0054515 (Pelargonidin 3-(6''-caffeylglucoside))

3D MOL for NP0054515 (Pelargonidin 3-(6''-caffeylglucoside))

3D SDF for NP0054515 (Pelargonidin 3-(6''-caffeylglucoside))

3D-SDF for NP0054515 (Pelargonidin 3-(6''-caffeylglucoside))

PDB for NP0054515 (Pelargonidin 3-(6''-caffeylglucoside))

3D PDB for NP0054515 (Pelargonidin 3-(6''-caffeylglucoside))

SMILES for NP0054515 (Pelargonidin 3-(6''-caffeylglucoside))

INCHI for NP0054515 (Pelargonidin 3-(6''-caffeylglucoside))

Structure for NP0054515 (Pelargonidin 3-(6''-caffeylglucoside))

3D Structure for NP0054515 (Pelargonidin 3-(6''-caffeylglucoside))