NP-MRD: Showing NP-Card for (+)-Isolarisiresinol 3a-O-beta-D-glucopyranoside (NP0077405)

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Record Information

Version

2.0

Created at

2022-04-28 22:33:57 UTC

Updated at

2022-04-28 22:33:57 UTC

NP-MRD ID

NP0077405

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Isolarisiresinol 3a-O-beta-D-glucopyranoside

Description

(+)-Isolariciresinol 9'-O-glucoside 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. (+)-Isolarisiresinol 3a-O-beta-D-glucopyranoside is found in Glochidion zeylanicum, Gnetum montanum, Meehania urticifolia, Myrsine africana, Myrsine seguinii, Pedicularis densispica, Pinus sylvestris , Sauropus androgynus and Sedum sarmentosum. Based on a literature review very few articles have been published on (+)-Isolariciresinol 9'-O-glucoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200342D          

 37 40  0  0  1  0            999 V2000
    0.7145   -1.2375    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


  Mrv1652304292200342D          

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 16 17  1  0  0  0  0
 18 17  1  1  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
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 22 24  1  1  0  0  0
 24 25  1  0  0  0  0
 21 26  1  6  0  0  0
 20 27  1  1  0  0  0
 19 28  1  6  0  0  0
  4 29  1  6  0  0  0
 29 30  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
  1 34  1  0  0  0  0
 33 35  1  0  0  0  0
 32 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077405

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1O)[C@@H]([C@@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](CO)C2)C1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O11/c1-34-19-6-12(3-4-17(19)29)22-15-8-18(30)20(35-2)7-13(15)5-14(9-27)16(22)11-36-26-25(33)24(32)23(31)21(10-28)37-26/h3-4,6-8,14,16,21-33H,5,9-11H2,1-2H3/t14-,16-,21+,22-,23+,24-,25+,26+/m0/s1

> <INCHI_KEY>
AHYOMNWKYGMYMB-QBCFYRCNSA-N

> <FORMULA>
C26H34O11

> <MOLECULAR_WEIGHT>
522.547

> <EXACT_MASS>
522.210111915

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
53.98211830934813

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.35

> <JCHEM_LOGP>
0.009602690000001496

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.454636238136382

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.836336873554703

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6036931612246734

> <JCHEM_POLAR_SURFACE_AREA>
178.52999999999997

> <JCHEM_REFRACTIVITY>
130.28589999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001  -6.930   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  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
CONECT    1    2    6   34                                                  
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   29                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10                                                            
CONECT   14    9   15                                                       
CONECT   15   14                                                            
CONECT   16    5   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   28                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   18                                                       
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   21                                                            
CONECT   27   20                                                            
CONECT   28   19                                                            
CONECT   29    4   30                                                       
CONECT   30   29                                                            
CONECT   31    2   32                                                       
CONECT   32   31   33   36                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33    1                                                       
CONECT   35   33                                                            
CONECT   36   32   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

C₂₆H₃₄O₁₁

Average Mass

522.5470 Da

Monoisotopic Mass

522.21011 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-{[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1O)[C@@H]([C@@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](CO)C2)C1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C26H34O11/c1-34-19-6-12(3-4-17(19)29)22-15-8-18(30)20(35-2)7-13(15)5-14(9-27)16(22)11-36-26-25(33)24(32)23(31)21(10-28)37-26/h3-4,6-8,14,16,21-33H,5,9-11H2,1-2H3/t14-,16-,21+,22-,23+,24-,25+,26+/m0/s1

InChI Key

AHYOMNWKYGMYMB-QBCFYRCNSA-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
Glochidion zeylanicum	LOTUS Database	35616633
Gnetum montanum	LOTUS Database	35616633
Meehania urticifolia	LOTUS Database	35616633
Myrsine africana	LOTUS Database	35616633
Myrsine seguinii	Plant	KNApSAcK
Pedicularis densispica	LOTUS Database	35616633
Pinus sylvestris	Plant	KNApSAcK
Sauropus androgynus	LOTUS Database	35616633
Sedum sarmentosum	LOTUS Database	35616633

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
1-aryltetralin lignan
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Tetralin
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Ether
Primary alcohol
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	0.35	ALOGPS
logP	0.0096	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.84	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	178.53 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.29 m³·mol⁻¹	ChemAxon
Polarizability	53.98 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

Not Available

Chemspider ID

33823924

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

93473218

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Isolarisiresinol 3a-O-beta-D-glucopyranoside (NP0077405)

MOL for NP0077405 ((+)-Isolarisiresinol 3a-O-beta-D-glucopyranoside)

3D MOL for NP0077405 ((+)-Isolarisiresinol 3a-O-beta-D-glucopyranoside)

3D SDF for NP0077405 ((+)-Isolarisiresinol 3a-O-beta-D-glucopyranoside)

3D-SDF for NP0077405 ((+)-Isolarisiresinol 3a-O-beta-D-glucopyranoside)

PDB for NP0077405 ((+)-Isolarisiresinol 3a-O-beta-D-glucopyranoside)

3D PDB for NP0077405 ((+)-Isolarisiresinol 3a-O-beta-D-glucopyranoside)

SMILES for NP0077405 ((+)-Isolarisiresinol 3a-O-beta-D-glucopyranoside)

INCHI for NP0077405 ((+)-Isolarisiresinol 3a-O-beta-D-glucopyranoside)

Structure for NP0077405 ((+)-Isolarisiresinol 3a-O-beta-D-glucopyranoside)

3D Structure for NP0077405 ((+)-Isolarisiresinol 3a-O-beta-D-glucopyranoside)