NP-MRD: Showing NP-Card for (2r,3r)-4-(acetyloxy)-3-(2h-1,3-benzodioxol-5-ylmethyl)-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate (NP0196042)

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Record Information

Version

2.0

Created at

2022-09-04 14:02:06 UTC

Updated at

2022-09-04 14:02:07 UTC

NP-MRD ID

NP0196042

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r)-4-(acetyloxy)-3-(2h-1,3-benzodioxol-5-ylmethyl)-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate

Description

(?)-Dihydroclusin diacetate belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. (2r,3r)-4-(acetyloxy)-3-(2h-1,3-benzodioxol-5-ylmethyl)-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate is found in Bursera microphylla and Justicia procumbens. Based on a literature review very few articles have been published on (?)-Dihydroclusin diacetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042216022D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042216022D          

 35 37  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0196042

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C[C@@H](COC(C)=O)[C@H](COC(C)=O)CC2=CC=C3OCOC3=C2)=CC(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O9/c1-16(27)32-13-20(8-18-6-7-22-23(10-18)35-15-34-22)21(14-33-17(2)28)9-19-11-24(29-3)26(31-5)25(12-19)30-4/h6-7,10-12,20-21H,8-9,13-15H2,1-5H3/t20-,21-/m0/s1

> <INCHI_KEY>
PGLVKIQODAEYPR-SFTDATJTSA-N

> <FORMULA>
C26H32O9

> <MOLECULAR_WEIGHT>
488.533

> <EXACT_MASS>
488.20463261

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.556562823974744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-4-(acetyloxy)-3-[(2H-1,3-benzodioxol-5-yl)methyl]-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate

> <JCHEM_LOGP>
3.287804748666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.266300313030858

> <JCHEM_POLAR_SURFACE_AREA>
98.75000000000001

> <JCHEM_REFRACTIVITY>
125.85830000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-4-(acetyloxy)-3-(2H-1,3-benzodioxol-5-ylmethyl)-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+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  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.322 -13.826   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.854 -13.987   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.480 -12.580   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   13   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29    5   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30    3   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
(?)-dihydroclusin diacetic acid	Generator

Chemical Formula

C₂₆H₃₂O₉

Average Mass

488.5330 Da

Monoisotopic Mass

488.20463 Da

IUPAC Name

(2R,3R)-4-(acetyloxy)-3-[(2H-1,3-benzodioxol-5-yl)methyl]-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate

Traditional Name

(2R,3R)-4-(acetyloxy)-3-(2H-1,3-benzodioxol-5-ylmethyl)-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(C[C@@H](COC(C)=O)[C@H](COC(C)=O)CC2=CC=C3OCOC3=C2)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C26H32O9/c1-16(27)32-13-20(8-18-6-7-22-23(10-18)35-15-34-22)21(14-33-17(2)28)9-19-11-24(29-3)26(31-5)25(12-19)30-4/h6-7,10-12,20-21H,8-9,13-15H2,1-5H3/t20-,21-/m0/s1

InChI Key

PGLVKIQODAEYPR-SFTDATJTSA-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
Bursera microphylla	LOTUS Database	35616633
Justicia procumbens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Not Available

Direct Parent

Dibenzylbutane lignans

Alternative Parents

Substituents

Dibenzylbutane lignan skeleton
Benzodioxole
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Carboxylic acid ester
Organoheterocyclic compound
Acetal
Ether
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	3.29	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	98.75 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	125.86 m³·mol⁻¹	ChemAxon
Polarizability	51.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

10229319

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bracket

METLIN ID

Not Available

PubChem Compound

21600064

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r)-4-(acetyloxy)-3-(2h-1,3-benzodioxol-5-ylmethyl)-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate (NP0196042)

MOL for NP0196042 ((2r,3r)-4-(acetyloxy)-3-(2h-1,3-benzodioxol-5-ylmethyl)-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate)

3D MOL for NP0196042 ((2r,3r)-4-(acetyloxy)-3-(2h-1,3-benzodioxol-5-ylmethyl)-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate)

3D SDF for NP0196042 ((2r,3r)-4-(acetyloxy)-3-(2h-1,3-benzodioxol-5-ylmethyl)-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate)

3D-SDF for NP0196042 ((2r,3r)-4-(acetyloxy)-3-(2h-1,3-benzodioxol-5-ylmethyl)-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate)

PDB for NP0196042 ((2r,3r)-4-(acetyloxy)-3-(2h-1,3-benzodioxol-5-ylmethyl)-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate)

3D PDB for NP0196042 ((2r,3r)-4-(acetyloxy)-3-(2h-1,3-benzodioxol-5-ylmethyl)-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate)

SMILES for NP0196042 ((2r,3r)-4-(acetyloxy)-3-(2h-1,3-benzodioxol-5-ylmethyl)-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate)

INCHI for NP0196042 ((2r,3r)-4-(acetyloxy)-3-(2h-1,3-benzodioxol-5-ylmethyl)-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate)

Structure for NP0196042 ((2r,3r)-4-(acetyloxy)-3-(2h-1,3-benzodioxol-5-ylmethyl)-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate)

3D Structure for NP0196042 ((2r,3r)-4-(acetyloxy)-3-(2h-1,3-benzodioxol-5-ylmethyl)-2-[(3,4,5-trimethoxyphenyl)methyl]butyl acetate)