NP-MRD: Showing NP-Card for lancilignanside A (NP0039502)

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Record Information

Version

2.0

Created at

2021-06-20 21:54:53 UTC

Updated at

2021-06-30 00:12:52 UTC

NP-MRD ID

NP0039502

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lancilignanside A

Provided By

JEOL Database JEOL Logo

Description

Lancilignanside A belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. lancilignanside A is found in Schisandra lancifolia. lancilignanside A was first documented in 2010 (Xiao, W.-L., et al.). Based on a literature review very few articles have been published on Lancilignanside A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123543D          

 67 72  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202123543D          

 67 72  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0039502

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@]1([H])[C@]([H])(O[C@]2([H])C3=C([H])C([H])=C(OC([H])([H])[C@@]4([H])O[C@@]([H])(OC([H])([H])[C@@]12[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]4([H])O[H])C(OC([H])([H])[H])=C3[H])C1=C([H])C2=C(OC([H])([H])O2)C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O11/c1-31-18-6-12-2-4-16(18)32-10-20-21(28)22(29)23(30)26(36-20)33-9-15-14(8-27)24(37-25(12)15)13-3-5-17-19(7-13)35-11-34-17/h2-7,14-15,20-30H,8-11H2,1H3/t14-,15-,20+,21+,22-,23+,24+,25+,26+/m0/s1

> <INCHI_KEY>
YETYPWMXADAFPR-WMYFGKAISA-N

> <FORMULA>
C26H30O11

> <MOLECULAR_WEIGHT>
518.515

> <EXACT_MASS>
518.178811786

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
52.760307131414756

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4S,5R,6R,9R,10R,11S,12S,13R)-4-(2H-1,3-benzodioxol-5-yl)-5-(hydroxymethyl)-20-methoxy-3,8,15,21-tetraoxatetracyclo[14.2.2.1^{9,13}.0^{2,6}]henicosa-1(18),16,19-triene-10,11,12-triol

> <ALOGPS_LOGP>
0.56

> <JCHEM_LOGP>
0.09416150900000117

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.212286184872802

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.212291458016667

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6413960106920618

> <JCHEM_POLAR_SURFACE_AREA>
145.53000000000003

> <JCHEM_REFRACTIVITY>
124.56740000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S,5R,6R,9R,10R,11S,12S,13R)-4-(2H-1,3-benzodioxol-5-yl)-5-(hydroxymethyl)-20-methoxy-3,8,15,21-tetraoxatetracyclo[14.2.2.1^{9,13}.0^{2,6}]henicosa-1(18),16,19-triene-10,11,12-triol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       0.226  -3.278   5.661  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.456  -2.753   4.523  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.258  -1.828   3.809  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.510  -0.854   3.180  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.086   0.042   2.278  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.483   0.127   2.215  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.256  -0.844   2.840  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.623  -1.888   3.517  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.319  -3.038   3.777  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.691  -3.733   2.560  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.496  -4.264   1.716  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.973  -3.219   0.853  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.163  -3.642   0.094  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.670  -2.586  -0.753  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.378  -1.575  -0.018  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.586  -0.269  -0.074  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.761   0.618   1.164  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.326   1.923   0.770  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.384   2.022  -0.675  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.092   3.314  -1.037  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.692   4.509  -0.381  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.278   5.745  -0.675  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.261   5.770  -1.635  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.658   4.628  -2.287  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.096   3.395  -2.017  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.637   4.867  -3.200  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.813   6.290  -3.043  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.939   6.871  -2.053  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.986   0.701  -1.182  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.456   0.304  -2.558  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.073  -0.895  -3.008  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.236  -4.787  -0.854  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.890  -5.277  -1.600  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.819  -5.937  -0.043  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.313  -6.964  -0.917  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.962  -5.448   0.847  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.411  -6.542   1.651  0.00  0.00           O+0
HETATM   38  H   UNK     0       0.800  -4.167   5.384  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.534  -3.591   6.384  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.862  -2.533   6.152  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.592  -0.894   3.284  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.963   0.847   1.557  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.331  -0.857   2.687  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.298  -4.574   2.912  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.353  -3.104   1.952  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.702  -4.583   2.403  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.970  -3.975   0.760  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.355  -1.455  -0.498  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.577  -1.911   1.002  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.478  -0.508  -0.222  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.812   0.701   1.468  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.656   2.110  -1.016  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.088   4.467   0.380  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.969   6.649  -0.163  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.449   2.532  -2.569  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.852   6.485  -2.751  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.623   6.776  -4.007  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.083   0.748  -1.208  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.629   0.152  -2.549  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.672   1.079  -3.299  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.740  -1.622  -2.444  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.969  -4.439  -1.592  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.297  -4.489  -2.012  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.041  -6.416   0.565  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.594  -7.115  -1.564  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.807  -5.144   0.215  0.00  0.00           H+0
HETATM   67  H   UNK     0       2.510  -7.294   1.030  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2    3    1                                                       
CONECT    3    8    4    2                                                  
CONECT    4    3    5   41                                                  
CONECT    5   17    4    6                                                  
CONECT    6    5    7   42                                                  
CONECT    7    8    6   43                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10   11    9   44   45                                             
CONECT   11   10   12   36   46                                             
CONECT   12   11   13                                                       
CONECT   13   14   32   12   47                                             
CONECT   14   13   15                                                       
CONECT   15   16   14   48   49                                             
CONECT   16   29   17   15   50                                             
CONECT   17   18   16    5   51                                             
CONECT   18   17   19                                                       
CONECT   19   18   29   20   52                                             
CONECT   20   21   25   19                                                  
CONECT   21   20   22   53                                                  
CONECT   22   23   21   54                                                  
CONECT   23   28   24   22                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   20   55                                                  
CONECT   26   24   27                                                       
CONECT   27   26   28   56   57                                             
CONECT   28   23   27                                                       
CONECT   29   19   16   30   58                                             
CONECT   30   29   31   59   60                                             
CONECT   31   30   61                                                       
CONECT   32   33   34   13   62                                             
CONECT   33   32   63                                                       
CONECT   34   36   32   35   64                                             
CONECT   35   34   65                                                       
CONECT   36   37   11   34   66                                             
CONECT   37   36   67                                                       
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    4                                                            
CONECT   42    6                                                            
CONECT   43    7                                                            
CONECT   44   10                                                            
CONECT   45   10                                                            
CONECT   46   11                                                            
CONECT   47   13                                                            
CONECT   48   15                                                            
CONECT   49   15                                                            
CONECT   50   16                                                            
CONECT   51   17                                                            
CONECT   52   19                                                            
CONECT   53   21                                                            
CONECT   54   22                                                            
CONECT   55   25                                                            
CONECT   56   27                                                            
CONECT   57   27                                                            
CONECT   58   29                                                            
CONECT   59   30                                                            
CONECT   60   30                                                            
CONECT   61   31                                                            
CONECT   62   32                                                            
CONECT   63   33                                                            
CONECT   64   34                                                            
CONECT   65   35                                                            
CONECT   66   36                                                            
CONECT   67   37                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  144    0
END

RDKit          3D

67 72  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₁₁

Average Mass

518.5150 Da

Monoisotopic Mass

518.17881 Da

IUPAC Name

(2S,4S,5R,6R,9R,10R,11S,12S,13R)-4-(2H-1,3-benzodioxol-5-yl)-5-(hydroxymethyl)-20-methoxy-3,8,15,21-tetraoxatetracyclo[14.2.2.1^{9,13}.0^{2,6}]henicosa-1(18),16,19-triene-10,11,12-triol

Traditional Name

(2S,4S,5R,6R,9R,10R,11S,12S,13R)-4-(2H-1,3-benzodioxol-5-yl)-5-(hydroxymethyl)-20-methoxy-3,8,15,21-tetraoxatetracyclo[14.2.2.1^{9,13}.0^{2,6}]henicosa-1(18),16,19-triene-10,11,12-triol

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@]1([H])[C@]([H])(O[C@]2([H])C3=C([H])C([H])=C(OC([H])([H])[C@@]4([H])O[C@@]([H])(OC([H])([H])[C@@]12[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]4([H])O[H])C(OC([H])([H])[H])=C3[H])C1=C([H])C2=C(OC([H])([H])O2)C([H])=C1[H]

InChI Identifier

InChI=1S/C26H30O11/c1-31-18-6-12-2-4-16(18)32-10-20-21(28)22(29)23(30)26(36-20)33-9-15-14(8-27)24(37-25(12)15)13-3-5-17-19(7-13)35-11-34-17/h2-7,14-15,20-30H,8-11H2,1H3/t14-,15-,20+,21+,22-,23+,24+,25+,26+/m0/s1

InChI Key

YETYPWMXADAFPR-WMYFGKAISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Schisandra lancifolia	JEOL database	Xiao, W.-L., et al, Chem. Pharm. Bull. 58, 852(2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Anisole
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Oxolane
Secondary alcohol
Acetal
Oxacycle
Polyol
Ether
Dialkyl ether
Organic oxygen compound
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.56	ALOGPS
logP	0.094	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	145.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	124.57 m³·mol⁻¹	ChemAxon
Polarizability	52.76 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

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

46830764

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xiao, W.-L., et al. (2010). Xiao, W.-L., et al, Chem. Pharm. Bull. 58, 852(2010). Chem. Pharm. Bull..

Showing NP-Card for lancilignanside A (NP0039502)

MOL for NP0039502 (lancilignanside A)

3D MOL for NP0039502 (lancilignanside A)

3D SDF for NP0039502 (lancilignanside A)

3D-SDF for NP0039502 (lancilignanside A)

PDB for NP0039502 (lancilignanside A)

3D PDB for NP0039502 (lancilignanside A)

SMILES for NP0039502 (lancilignanside A)

INCHI for NP0039502 (lancilignanside A)

Structure for NP0039502 (lancilignanside A)

3D Structure for NP0039502 (lancilignanside A)