NP-MRD: Showing NP-Card for Lobetyolinin (NP0140350)

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Record Information

Version

2.0

Created at

2022-06-29 21:27:27 UTC

Updated at

2022-06-29 21:27:27 UTC

NP-MRD ID

NP0140350

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lobetyolinin

Description

Lobetyolinin belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Lobetyolinin is found in Campanula glomerata, Codonopsis clematidea, Lobelia cardinalis, Lobelia chinensis, Lobelia inflata, Lobelia sessilifolia, Platycodon grandiflorus and Pratia nummularia. Lobetyolinin was first documented in 2018 (PMID: 30483130). Based on a literature review a small amount of articles have been published on Lobetyolinin (PMID: 33930986) (PMID: 33161560) (PMID: 30717158).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292223272D          

 39 40  0  0  0  0            999 V2000
    5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

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M  END


  Mrv1652306292223272D          

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   -3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  3  0  0  0  0
  5  6  1  0  0  0  0
  6  7  3  0  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  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
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 28 33  1  0  0  0  0
 27 34  1  0  0  0  0
 26 35  1  0  0  0  0
 20 36  1  0  0  0  0
 19 37  1  0  0  0  0
 18 38  1  0  0  0  0
  8 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\C#CC#CC(O)C(OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)\C=C\CCCO

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O13/c1-2-3-4-5-7-10-15(29)16(11-8-6-9-12-27)37-26-24(35)22(33)20(31)18(39-26)14-36-25-23(34)21(32)19(30)17(13-28)38-25/h2-3,8,11,15-35H,6,9,12-14H2,1H3/b3-2+,11-8+

> <INCHI_KEY>
GDLSOFWVVAOUJI-FWTOVJONSA-N

> <FORMULA>
C26H38O13

> <MOLECULAR_WEIGHT>
558.577

> <EXACT_MASS>
558.231241284

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
57.97278793611339

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(4E,12E)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.05

> <JCHEM_LOGP>
-1.9948998933333333

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.221412002292514

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.77423358662231

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083422322401

> <JCHEM_POLAR_SURFACE_AREA>
218.98999999999998

> <JCHEM_REFRACTIVITY>
136.6505

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(4E,12E)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -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  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0     -10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   39                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    9   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   38                                                  
CONECT   19   18   20   37                                                  
CONECT   20   19   21   36                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   17                                                       
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   35                                                  
CONECT   27   26   28   34                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   25                                                       
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   28                                                            
CONECT   34   27                                                            
CONECT   35   26                                                            
CONECT   36   20                                                            
CONECT   37   19                                                            
CONECT   38   18                                                            
CONECT   39    8                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₈O₁₃

Average Mass

558.5770 Da

Monoisotopic Mass

558.23124 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C\C#CC#CC(O)C(OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)\C=C\CCCO

InChI Identifier

InChI=1S/C26H38O13/c1-2-3-4-5-7-10-15(29)16(11-8-6-9-12-27)37-26-24(35)22(33)20(31)18(39-26)14-36-25-23(34)21(32)19(30)17(13-28)38-25/h2-3,8,11,15-35H,6,9,12-14H2,1H3/b3-2+,11-8+

InChI Key

GDLSOFWVVAOUJI-FWTOVJONSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Campanula glomerata	LOTUS Database	35616633
Codonopsis clematidea	LOTUS Database	35616633
Lobelia cardinalis	LOTUS Database	35616633
Lobelia chinensis	LOTUS Database	35616633
Lobelia inflata	LOTUS Database	35616633
Lobelia sessilifolia	LOTUS Database	35616633
Platycodon grandiflorus	LOTUS Database	35616633
Pratia nummularia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Long chain fatty alcohol
Alkyl glycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
Fatty alcohol
Oxane
Secondary alcohol
Polyol
Oxacycle
Acetal
Organoheterocyclic compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00030685

Chemspider ID

4573048

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5459227

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Phan NHT, Thuan NTD, Hien NTT, Huyen PV, Duyen NHH, Hanh TTH, Cuong NX, Quang TH, Nam NH, Minh CV: Polyacetylene and phenolic constituents from the roots of Codonopsis javanica. Nat Prod Res. 2020 Oct 14:1-7. doi: 10.1080/14786419.2020.1833200. [PubMed:33930986 ]
Bailly C: Anticancer Properties of Lobetyolin, an Essential Component of Radix Codonopsis (Dangshen). Nat Prod Bioprospect. 2021 Apr;11(2):143-153. doi: 10.1007/s13659-020-00283-9. Epub 2020 Nov 7. [PubMed:33161560 ]
Ji JJ, Feng Q, Sun HF, Zhang XJ, Li XX, Li JK, Gao JP: Response of Bioactive Metabolite and Biosynthesis Related Genes to Methyl Jasmonate Elicitation in Codonopsis pilosula. Molecules. 2019 Feb 1;24(3):533. doi: 10.3390/molecules24030533. [PubMed:30717158 ]
Liu H, Chen X, Zhao X, Zhao B, Qian K, Shi Y, Baruscotti M, Wang Y: Screening and Identification of Cardioprotective Compounds From Wenxin Keli by Activity Index Approach and in vivo Zebrafish Model. Front Pharmacol. 2018 Nov 13;9:1288. doi: 10.3389/fphar.2018.01288. eCollection 2018. [PubMed:30483130 ]

Showing NP-Card for Lobetyolinin (NP0140350)

MOL for NP0140350 (Lobetyolinin)

3D MOL for NP0140350 (Lobetyolinin)

3D SDF for NP0140350 (Lobetyolinin)

3D-SDF for NP0140350 (Lobetyolinin)

PDB for NP0140350 (Lobetyolinin)

3D PDB for NP0140350 (Lobetyolinin)

SMILES for NP0140350 (Lobetyolinin)

INCHI for NP0140350 (Lobetyolinin)

Structure for NP0140350 (Lobetyolinin)

3D Structure for NP0140350 (Lobetyolinin)