NP-MRD: Showing NP-Card for (-)-Phlomisethanoside (NP0076966)

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Record Information

Version

2.0

Created at

2022-04-28 22:08:51 UTC

Updated at

2022-04-28 22:08:51 UTC

NP-MRD ID

NP0076966

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Phlomisethanoside

Description

Phlomisethanoside belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. (-)-Phlomisethanoside is found in Catalpa ovata, Phlomis grandiflora and Phlomis grandiflora var. grandiflora. (-)-Phlomisethanoside was first documented in 2017 (PMID: 28626476). Based on a literature review very few articles have been published on Phlomisethanoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200082D          

 41 44  0  0  1  0            999 V2000
    2.1777   -2.6780    0.0000 C   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


  Mrv1652304292200082D          

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    5.3051   -0.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7101   -0.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5350   -0.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9550   -0.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5500   -1.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7250   -1.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7799   -0.7124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9400    0.7079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7650    0.7165    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
  1  5  1  0  0  0  0
  4  6  1  6  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  1  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  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
 19 22  1  0  0  0  0
 10 23  1  1  0  0  0
 23 24  1  0  0  0  0
  9 25  1  6  0  0  0
  8 26  1  1  0  0  0
  3 27  1  1  0  0  0
  2 28  1  1  0  0  0
  2 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 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
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
 36 39  1  0  0  0  0
 35 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076966

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C(=O)OC[C@@]1(O)CO[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OCCC2=CC=C(O)C=C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O14/c1-36-18-10-15(4-7-17(18)30)24(34)38-12-27(35)13-39-26(23(27)33)41-22-21(32)20(31)19(11-28)40-25(22)37-9-8-14-2-5-16(29)6-3-14/h2-7,10,19-23,25-26,28-33,35H,8-9,11-13H2,1H3/t19-,20-,21+,22-,23+,25-,26+,27-/m1/s1

> <INCHI_KEY>
JCVAJYVLSZBGRV-DVKXAIPJSA-N

> <FORMULA>
C27H34O14

> <MOLECULAR_WEIGHT>
582.555

> <EXACT_MASS>
582.194855775

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
58.70788108030323

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(3S,4R,5S)-5-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate

> <ALOGPS_LOGP>
0.31

> <JCHEM_LOGP>
0.17772048766666615

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.217166394199822

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.964858683825735

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810836372259617

> <JCHEM_POLAR_SURFACE_AREA>
214.05999999999997

> <JCHEM_REFRACTIVITY>
136.9594

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3S,4R,5S)-5-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       4.065  -4.999   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.311  -4.094   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.557  -4.999   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.081  -6.464   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.541  -6.464   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       6.986  -7.709   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.360  -9.116   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.265 -10.362   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.639 -11.769   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.107 -11.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.202 -10.684   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.828  -9.277   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.923  -8.031   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.391  -8.192   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.486  -6.946   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.045  -7.107   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.672  -8.514   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.203  -8.675   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.108  -7.429   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.482  -6.023   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.950  -5.862   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.640  -7.590   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.481 -13.337   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.949 -13.498   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.544 -13.015   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.797 -10.201   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.021  -4.523   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.555  -2.752   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.067  -2.752   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.607  -2.736   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.363  -1.394   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.579  -0.069   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.903  -1.378   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.659  -0.036   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.199  -0.020   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.983  -1.346   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.227  -2.688   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.687  -2.704   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      14.523  -1.330   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      12.955   1.321   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      14.495   1.337   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3   28   29                                             
CONECT    3    2    4   27                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   26                                                  
CONECT    9    8   10   25                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19                                                            
CONECT   23   10   24                                                       
CONECT   24   23                                                            
CONECT   25    9                                                            
CONECT   26    8                                                            
CONECT   27    3                                                            
CONECT   28    2                                                            
CONECT   29    2   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37   33                                                       
CONECT   39   36                                                            
CONECT   40   35   41                                                       
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₁₄

Average Mass

582.5550 Da

Monoisotopic Mass

582.19486 Da

IUPAC Name

[(3S,4R,5S)-5-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate

Traditional Name

[(3S,4R,5S)-5-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)C(=O)OC[C@@]1(O)CO[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OCCC2=CC=C(O)C=C2)[C@@H]1O

InChI Identifier

InChI=1S/C27H34O14/c1-36-18-10-15(4-7-17(18)30)24(34)38-12-27(35)13-39-26(23(27)33)41-22-21(32)20(31)19(11-28)40-25(22)37-9-8-14-2-5-16(29)6-3-14/h2-7,10,19-23,25-26,28-33,35H,8-9,11-13H2,1H3/t19-,20-,21+,22-,23+,25-,26+,27-/m1/s1

InChI Key

JCVAJYVLSZBGRV-DVKXAIPJSA-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
Catalpa ovata	LOTUS Database	35616633
Phlomis grandiflora	LOTUS Database	35616633
Phlomis grandiflora var. grandiflora	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Disaccharide
O-glycosyl compound
Glycosyl compound
M-methoxybenzoic acid or derivatives
Methoxyphenol
Benzoate ester
Tyrosol derivative
Benzoic acid or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Oxane
Benzenoid
Monocyclic benzene moiety
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Alcohol
Organic oxygen compound
Primary alcohol
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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	0.31	ALOGPS
logP	0.18	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	8.96	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	214.06 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	136.96 m³·mol⁻¹	ChemAxon
Polarizability	58.71 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

C00039991

Chemspider ID

90660137

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100978506

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Delazar A, Nazemiyeh H, Afshar FH, Barghi N, Esnaashari S, Asgharian P: Chemical compositions and biological activities of Scutellaria pinnatifida A. Hamilt aerial parts. Res Pharm Sci. 2017 Jun;12(3):187-195. doi: 10.4103/1735-5362.207199. [PubMed:28626476 ]

Showing NP-Card for (-)-Phlomisethanoside (NP0076966)

MOL for NP0076966 ((-)-Phlomisethanoside)

3D MOL for NP0076966 ((-)-Phlomisethanoside)

3D SDF for NP0076966 ((-)-Phlomisethanoside)

3D-SDF for NP0076966 ((-)-Phlomisethanoside)

PDB for NP0076966 ((-)-Phlomisethanoside)

3D PDB for NP0076966 ((-)-Phlomisethanoside)

SMILES for NP0076966 ((-)-Phlomisethanoside)

INCHI for NP0076966 ((-)-Phlomisethanoside)

Structure for NP0076966 ((-)-Phlomisethanoside)

3D Structure for NP0076966 ((-)-Phlomisethanoside)