NP-MRD: Showing NP-Card for (+)-Dichotomoside B (NP0072060)

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Record Information

Version

2.0

Created at

2022-04-28 17:26:30 UTC

Updated at

2022-04-28 17:26:30 UTC

NP-MRD ID

NP0072060

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Dichotomoside B

Description

Dichotomoside B 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. (+)-Dichotomoside B is found in Stellaria dichotoma and Stellaria dichotoma L.var.lanceolata. Based on a literature review very few articles have been published on Dichotomoside B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219262D          

 43 45  0  0  1  0            999 V2000
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    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
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  1 39  1  0  0  0  0
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 41 43  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282219262D          

 43 45  0  0  1  0            999 V2000
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   -6.4302   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -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
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    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
    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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    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  1  0  0  0  0
  4  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  1  0  0  0
 21 24  1  6  0  0  0
 20 25  1  1  0  0  0
 19 26  1  6  0  0  0
 26 27  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
  1 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072060

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCOC(=O)CCC1=CC(OC)=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=C1)C1=C(O)C(OC)=CC(CCC(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O13/c1-4-5-10-41-24(34)9-7-17-12-19(18-11-16(6-8-23(32)33)13-20(39-2)25(18)35)29(21(14-17)40-3)43-30-28(38)27(37)26(36)22(15-31)42-30/h11-14,22,26-28,30-31,35-38H,4-10,15H2,1-3H3,(H,32,33)/t22-,26-,27+,28-,30+/m1/s1

> <INCHI_KEY>
CQJZSGNCDIJTLR-ZHTDWIAYSA-N

> <FORMULA>
C30H40O13

> <MOLECULAR_WEIGHT>
608.637

> <EXACT_MASS>
608.246891348

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
63.6001039381222

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[5'-(3-butoxy-3-oxopropyl)-6-hydroxy-3',5-dimethoxy-2'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-[1,1'-biphenyl]-3-yl]propanoic acid

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
2.0643568893333333

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.452116213841666

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6598789665653646

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923574305965

> <JCHEM_POLAR_SURFACE_AREA>
201.66999999999996

> <JCHEM_REFRACTIVITY>
150.68670000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[5'-(3-butoxy-3-oxopropyl)-6-hydroxy-3',5-dimethoxy-2'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-[1,1'-biphenyl]-3-yl]propanoic acid

> <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      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -9.336   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+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      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0     -14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0     -14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -5.335   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    4                                                            
CONECT   10    3   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   30                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   28                                                  
CONECT   15   14   10   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   17   23                                                  
CONECT   23   22                                                            
CONECT   24   21                                                            
CONECT   25   20                                                            
CONECT   26   19   27                                                       
CONECT   27   26                                                            
CONECT   28   14   29                                                       
CONECT   29   28                                                            
CONECT   30   12   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39    1   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₀O₁₃

Average Mass

608.6370 Da

Monoisotopic Mass

608.24689 Da

IUPAC Name

3-[5'-(3-butoxy-3-oxopropyl)-6-hydroxy-3',5-dimethoxy-2'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-[1,1'-biphenyl]-3-yl]propanoic acid

Traditional Name

3-[5'-(3-butoxy-3-oxopropyl)-6-hydroxy-3',5-dimethoxy-2'-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-[1,1'-biphenyl]-3-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

CCCCOC(=O)CCC1=CC(OC)=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=C1)C1=C(O)C(OC)=CC(CCC(O)=O)=C1

InChI Identifier

InChI=1S/C30H40O13/c1-4-5-10-41-24(34)9-7-17-12-19(18-11-16(6-8-23(32)33)13-20(39-2)25(18)35)29(21(14-17)40-3)43-30-28(38)27(37)26(36)22(15-31)42-30/h11-14,22,26-28,30-31,35-38H,4-10,15H2,1-3H3,(H,32,33)/t22-,26-,27+,28-,30+/m1/s1

InChI Key

CQJZSGNCDIJTLR-ZHTDWIAYSA-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
Stellaria dichotoma	LOTUS Database	35616633
Stellaria dichotoma L.var.lanceolata	Plant	KNApSAcK

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Biphenyl
Hexose monosaccharide
O-glycosyl compound
3-phenylpropanoic-acid
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Fatty acid ester
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Monosaccharide
Oxane
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Ether
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Acetal
Polyol
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Primary 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	2.09	ALOGPS
logP	2.06	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.66	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	201.67 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	150.69 m³·mol⁻¹	ChemAxon
Polarizability	63.6 Å³	ChemAxon
Number of Rings	3	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

C00031743

Chemspider ID

9665221

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11490410

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Dichotomoside B (NP0072060)

MOL for NP0072060 ((+)-Dichotomoside B)

3D MOL for NP0072060 ((+)-Dichotomoside B)

3D SDF for NP0072060 ((+)-Dichotomoside B)

3D-SDF for NP0072060 ((+)-Dichotomoside B)

PDB for NP0072060 ((+)-Dichotomoside B)

3D PDB for NP0072060 ((+)-Dichotomoside B)

SMILES for NP0072060 ((+)-Dichotomoside B)

INCHI for NP0072060 ((+)-Dichotomoside B)

Structure for NP0072060 ((+)-Dichotomoside B)

3D Structure for NP0072060 ((+)-Dichotomoside B)