NP-MRD: Showing NP-Card for Suffruticoside B (NP0073200)

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Record Information

Version

2.0

Created at

2022-04-28 18:27:58 UTC

Updated at

2022-04-28 18:27:58 UTC

NP-MRD ID

NP0073200

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Suffruticoside B

Description

Suffruticoside B belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes: Hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol). Suffruticoside B is found in Paeonia moutan . Based on a literature review very few articles have been published on Suffruticoside B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220272D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282220272D          

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    1.2804   -3.1980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9448   -2.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1243   -2.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3606   -3.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1811   -2.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0251   -3.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2112   -1.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737   -0.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0942   -1.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4297   -1.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5791   -0.3557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2435    0.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  6  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 11 14  1  1  0  0  0
 14 15  1  0  0  0  0
 11 16  1  6  0  0  0
 10 17  1  6  0  0  0
  4 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  0  0  0  0
 24 28  1  0  0  0  0
 23 29  1  0  0  0  0
  3 30  1  6  0  0  0
  2 31  1  1  0  0  0
  1 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 34 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 33 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073200

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O[C@@H]2O[C@H](CO[C@@H]3OC[C@](O)(CO)[C@H]3O)[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O)[C@H]2O)=C(C=C1)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O16/c1-11(29)14-4-3-13(38-2)7-17(14)41-25-21(34)20(33)22(43-24(36)12-5-15(30)19(32)16(31)6-12)18(42-25)8-39-26-23(35)27(37,9-28)10-40-26/h3-7,18,20-23,25-26,28,30-35,37H,8-10H2,1-2H3/t18-,20-,21-,22-,23+,25-,26-,27-/m1/s1

> <INCHI_KEY>
IIYNOSFQRKUHOL-FZOOHXBBSA-N

> <FORMULA>
C27H32O16

> <MOLECULAR_WEIGHT>
612.537

> <EXACT_MASS>
612.16903495

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
58.479693927619465

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5R,6S)-6-(2-acetyl-5-methoxyphenoxy)-2-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-4,5-dihydroxyoxan-3-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
0.20

> <JCHEM_LOGP>
-0.8903065223333331

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.150192941028397

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.10308326359296

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1423790163389347

> <JCHEM_POLAR_SURFACE_AREA>
251.35999999999993

> <JCHEM_REFRACTIVITY>
139.48419999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R,5R,6S)-6-(2-acetyl-5-methoxyphenoxy)-2-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-4,5-dihydroxyoxan-3-yl 3,4,5-trihydroxybenzoate

> <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       3.922  -6.131   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.548  -7.537   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.079  -7.698   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.985  -6.452   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.358  -5.046   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.827  -4.885   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.263  -3.800   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.795  -3.961   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.700  -2.715   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.224  -1.250   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.470  -0.345   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.716  -1.250   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.240  -2.715   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.714   0.997   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.498   2.322   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      11.226   0.997   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.760  -0.774   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.516  -6.613   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.143  -8.020   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.237  -9.266   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.674  -8.181   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.579  -6.935   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.111  -7.096   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.737  -8.503   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.832  -9.749   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.301  -9.588   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.458 -11.156   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      15.269  -8.664   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      14.016  -5.850   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.706  -9.105   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       3.643  -8.783   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.390  -5.970   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.764  -4.563   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.232  -4.402   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.673  -5.648   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.205  -5.487   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -0.047  -7.054   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.394  -2.995   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.511  -1.749   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.042  -1.910   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.669  -3.317   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.948  -0.664   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       2.321   0.743   0.000  0.00  0.00           C+0
CONECT    1    2    6   32                                                  
CONECT    2    1    3   31                                                  
CONECT    3    2    4   30                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   14   16                                             
CONECT   12   11   13                                                       
CONECT   13   12    9                                                       
CONECT   14   11   15                                                       
CONECT   15   14                                                            
CONECT   16   11                                                            
CONECT   17   10                                                            
CONECT   18    4   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25                                                            
CONECT   28   24                                                            
CONECT   29   23                                                            
CONECT   30    3                                                            
CONECT   31    2                                                            
CONECT   32    1   33                                                       
CONECT   33   32   34   41                                                  
CONECT   34   33   35   38                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   34   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40   33                                                       
CONECT   42   40   43                                                       
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₁₆

Average Mass

612.5370 Da

Monoisotopic Mass

612.16903 Da

IUPAC Name

(2R,3S,4R,5R,6S)-6-(2-acetyl-5-methoxyphenoxy)-2-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-4,5-dihydroxyoxan-3-yl 3,4,5-trihydroxybenzoate

Traditional Name

(2R,3S,4R,5R,6S)-6-(2-acetyl-5-methoxyphenoxy)-2-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-4,5-dihydroxyoxan-3-yl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(O[C@@H]2O[C@H](CO[C@@H]3OC[C@](O)(CO)[C@H]3O)[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O)[C@H]2O)=C(C=C1)C(C)=O

InChI Identifier

InChI=1S/C27H32O16/c1-11(29)14-4-3-13(38-2)7-17(14)41-25-21(34)20(33)22(43-24(36)12-5-15(30)19(32)16(31)6-12)18(42-25)8-39-26-23(35)27(37,9-28)10-40-26/h3-7,18,20-23,25-26,28,30-35,37H,8-10H2,1-2H3/t18-,20-,21-,22-,23+,25-,26-,27-/m1/s1

InChI Key

IIYNOSFQRKUHOL-FZOOHXBBSA-N

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
Paeonia suffruticosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes: Hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Not Available

Direct Parent

Tannins

Alternative Parents

Substituents

Tannin
Phenolic glycoside
Galloyl ester
Alkyl-phenylketone
Gallic acid or derivatives
O-glycosyl compound
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Glycosyl compound
Disaccharide
Benzoate ester
Phenylketone
Benzoic acid or derivatives
Benzenetriol
Acetophenone
Pyrogallol derivative
Benzoyl
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Anisole
Phenoxy compound
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Oxane
Monocyclic benzene moiety
Benzenoid
Oxolane
Tertiary alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Polyol
Acetal
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Ether
Organoheterocyclic compound
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aldehyde
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	0.2	ALOGPS
logP	-0.89	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.1	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	251.36 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	139.48 m³·mol⁻¹	ChemAxon
Polarizability	58.48 Å³	ChemAxon
Number of Rings	4	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00033397

Chemspider ID

8433688

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10258205

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Suffruticoside B (NP0073200)

MOL for NP0073200 (Suffruticoside B)

3D MOL for NP0073200 (Suffruticoside B)

3D SDF for NP0073200 (Suffruticoside B)

3D-SDF for NP0073200 (Suffruticoside B)

PDB for NP0073200 (Suffruticoside B)

3D PDB for NP0073200 (Suffruticoside B)

SMILES for NP0073200 (Suffruticoside B)

INCHI for NP0073200 (Suffruticoside B)

Structure for NP0073200 (Suffruticoside B)

3D Structure for NP0073200 (Suffruticoside B)