NP-MRD: Showing NP-Card for (+)-Tenuiphenone A (NP0071863)

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Record Information

Version

2.0

Created at

2022-04-28 17:14:13 UTC

Updated at

2022-04-28 17:14:13 UTC

NP-MRD ID

NP0071863

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Tenuiphenone A

Description

Tenuiphenone A 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. (+)-Tenuiphenone A is found in Polygala tenuifolia . Based on a literature review very few articles have been published on Tenuiphenone A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219142D          

 39 42  0  0  1  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    5.7158   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282219142D          

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 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 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
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 18 32  1  0  0  0  0
 12 33  1  1  0  0  0
 33 34  1  0  0  0  0
 11 35  1  6  0  0  0
 10 36  1  1  0  0  0
  3 37  1  1  0  0  0
  2 38  1  6  0  0  0
  1 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0071863

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)=CC(O)=C1C(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O13/c1-11-18(29)21(32)23(34)25(36-11)39-24-22(33)20(31)16(10-27)38-26(24)37-13-8-14(28)17(15(9-13)35-2)19(30)12-6-4-3-5-7-12/h3-9,11,16,18,20-29,31-34H,10H2,1-2H3/t11-,16+,18-,20+,21+,22-,23+,24+,25-,26+/m0/s1

> <INCHI_KEY>
YHDYMCMUHNAXIK-QLPIJONESA-N

> <FORMULA>
C26H32O13

> <MOLECULAR_WEIGHT>
552.529

> <EXACT_MASS>
552.18429109

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
54.720975019533924

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5R,6S)-2-{[(2S,3R,4S,5S,6R)-2-(4-benzoyl-3-hydroxy-5-methoxyphenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.09

> <JCHEM_LOGP>
0.3258031720000005

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.100162668648554

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.106165102593046

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092569339441

> <JCHEM_POLAR_SURFACE_AREA>
204.82999999999998

> <JCHEM_REFRACTIVITY>
130.0725

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.56e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5R,6S)-2-{[(2S,3R,4S,5S,6R)-2-(4-benzoyl-3-hydroxy-5-methoxyphenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

> <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       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.669 -12.320   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3   38                                                  
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   36                                                  
CONECT   11   10   12   35                                                  
CONECT   12   11   13   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   32                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   16                                                       
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   19   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   18                                                            
CONECT   33   12   34                                                       
CONECT   34   33                                                            
CONECT   35   11                                                            
CONECT   36   10                                                            
CONECT   37    3                                                            
CONECT   38    2                                                            
CONECT   39    1                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₁₃

Average Mass

552.5290 Da

Monoisotopic Mass

552.18429 Da

IUPAC Name

(2S,3R,4R,5R,6S)-2-{[(2S,3R,4S,5S,6R)-2-(4-benzoyl-3-hydroxy-5-methoxyphenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

Traditional Name

(2S,3R,4R,5R,6S)-2-{[(2S,3R,4S,5S,6R)-2-(4-benzoyl-3-hydroxy-5-methoxyphenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)=CC(O)=C1C(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C26H32O13/c1-11-18(29)21(32)23(34)25(36-11)39-24-22(33)20(31)16(10-27)38-26(24)37-13-8-14(28)17(15(9-13)35-2)19(30)12-6-4-3-5-7-12/h3-9,11,16,18,20-29,31-34H,10H2,1-2H3/t11-,16+,18-,20+,21+,22-,23+,24+,25-,26+/m0/s1

InChI Key

YHDYMCMUHNAXIK-QLPIJONESA-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
Polygala tenuifolia	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
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Benzophenone
Diphenylmethane
Aryl-phenylketone
Alkyl glycoside
Disaccharide
O-glycosyl compound
Methoxyphenol
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
Phenol ether
Aryl ketone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Oxane
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Secondary alcohol
Polyol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Primary alcohol
Aldehyde
Alcohol
Organic oxide
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	-0.09	ALOGPS
logP	0.33	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	7.11	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	204.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.07 m³·mol⁻¹	ChemAxon
Polarizability	54.72 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

C00031407

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101746681

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Tenuiphenone A (NP0071863)

MOL for NP0071863 ((+)-Tenuiphenone A)

3D MOL for NP0071863 ((+)-Tenuiphenone A)

3D SDF for NP0071863 ((+)-Tenuiphenone A)

3D-SDF for NP0071863 ((+)-Tenuiphenone A)

PDB for NP0071863 ((+)-Tenuiphenone A)

3D PDB for NP0071863 ((+)-Tenuiphenone A)

SMILES for NP0071863 ((+)-Tenuiphenone A)

INCHI for NP0071863 ((+)-Tenuiphenone A)

Structure for NP0071863 ((+)-Tenuiphenone A)

3D Structure for NP0071863 ((+)-Tenuiphenone A)