NP-MRD: Showing NP-Card for (-)-Styraxlignolide D (NP0079314)

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Record Information

Version

2.0

Created at

2022-04-29 00:20:41 UTC

Updated at

2022-04-29 00:20:41 UTC

NP-MRD ID

NP0079314

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Styraxlignolide D

Description

STYRAXLIGNOLIDE D belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. (-)-Styraxlignolide D is found in Carthamus tinctorius and Styrax japonica. (-)-Styraxlignolide D was first documented in 2004 (PMID: 15620237). Based on a literature review a small amount of articles have been published on STYRAXLIGNOLIDE D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202202D          

 37 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652304292202202D          

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 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 32 35  1  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079314

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(C[C@H]2[C@H](CC3=CC(OC)=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=C3)COC2=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O11/c1-33-19-9-14(3-5-17(19)28)8-16-15(12-35-25(16)32)7-13-4-6-18(20(10-13)34-2)36-26-24(31)23(30)22(29)21(11-27)37-26/h3-6,9-10,15-16,21-24,26-31H,7-8,11-12H2,1-2H3/t15-,16+,21-,22-,23+,24-,26-/m1/s1

> <INCHI_KEY>
FWRZDNFXFFWBGP-ZQJJHTFWSA-N

> <FORMULA>
C26H32O11

> <MOLECULAR_WEIGHT>
520.531

> <EXACT_MASS>
520.19446185

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.377443233881

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
1.09

> <JCHEM_LOGP>
1.0237144176666668

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.202181540681128

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.943135640673946

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354907191

> <JCHEM_POLAR_SURFACE_AREA>
164.37

> <JCHEM_REFRACTIVITY>
127.77879999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

> <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       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.803   1.425   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.803  -0.115   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.469  -0.885   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.137   2.195   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.470   1.425   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.804   2.195   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.138   1.425   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.138  -0.115   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.804  -0.885   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.470  -0.115   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.804  -2.425   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.138  -3.195   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      14.471  -0.885   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      14.471   2.195   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      11.804   3.735   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.469   3.735   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.803   4.505   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.572  -4.795   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.032  -4.795   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.127  -6.041   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.091  -2.854   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.771  -1.348   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.693  -0.872   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.014   0.634   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.131   1.665   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.595   1.189   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.916  -0.317   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.189   3.171   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -2.478   1.110   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.798   2.617   0.000  0.00  0.00           C+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   11                                                            
CONECT   17   10                                                            
CONECT   18    9                                                            
CONECT   19    3   20                                                       
CONECT   20   19                                                            
CONECT   21    1   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   22   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   32                                                            
CONECT   36   31   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₁₁

Average Mass

520.5310 Da

Monoisotopic Mass

520.19446 Da

IUPAC Name

(3S,4S)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

Traditional Name

(3S,4S)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(C[C@H]2[C@H](CC3=CC(OC)=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=C3)COC2=O)=C1

InChI Identifier

InChI=1S/C26H32O11/c1-33-19-9-14(3-5-17(19)28)8-16-15(12-35-25(16)32)7-13-4-6-18(20(10-13)34-2)36-26-24(31)23(30)22(29)21(11-27)37-26/h3-6,9-10,15-16,21-24,26-31H,7-8,11-12H2,1-2H3/t15-,16+,21-,22-,23+,24-,26-/m1/s1

InChI Key

FWRZDNFXFFWBGP-ZQJJHTFWSA-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
Carthamus tinctorius	LOTUS Database	35616633
Styrax japonica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Dibenzylbutyrolactone
Lignan lactone
Tetrahydrofuran lignan
9,9p-epoxylignan
Furanoid lignan
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Methoxyphenol
Phenol ether
Phenoxy compound
Methoxybenzene
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Fatty acyl
Gamma butyrolactone
Benzenoid
Monosaccharide
Oxane
Oxolane
Secondary alcohol
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Polyol
Acetal
Carboxylic acid derivative
Oxacycle
Ether
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
Primary alcohol
Organic oxygen compound
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	1.09	ALOGPS
logP	1.02	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.94	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164.37 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	127.78 m³·mol⁻¹	ChemAxon
Polarizability	52.38 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

C00043933

Chemspider ID

9355024

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11179934

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Min BS, Na MK, Oh SR, Ahn KS, Jeong GS, Li G, Lee SK, Joung H, Lee HK: New furofuran and butyrolactone lignans with antioxidant activity from the stem bark of Styrax japonica. J Nat Prod. 2004 Dec;67(12):1980-4. doi: 10.1021/np040113m. [PubMed:15620237 ]

Showing NP-Card for (-)-Styraxlignolide D (NP0079314)

MOL for NP0079314 ((-)-Styraxlignolide D)

3D MOL for NP0079314 ((-)-Styraxlignolide D)

3D SDF for NP0079314 ((-)-Styraxlignolide D)

3D-SDF for NP0079314 ((-)-Styraxlignolide D)

PDB for NP0079314 ((-)-Styraxlignolide D)

3D PDB for NP0079314 ((-)-Styraxlignolide D)

SMILES for NP0079314 ((-)-Styraxlignolide D)

INCHI for NP0079314 ((-)-Styraxlignolide D)

Structure for NP0079314 ((-)-Styraxlignolide D)

3D Structure for NP0079314 ((-)-Styraxlignolide D)