NP-MRD: Showing NP-Card for (3s,5s)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate (NP0296498)

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Record Information

Version

2.0

Created at

2022-09-10 06:06:42 UTC

Updated at

2022-09-10 06:06:43 UTC

NP-MRD ID

NP0296498

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,5s)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate

Description

(3S,5S)-1,7-Bis(3,4,5-trimethoxyphenyl)heptane-3,5-diol diacetate belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group. Based on a literature review very few articles have been published on (3S,5S)-1,7-Bis(3,4,5-trimethoxyphenyl)heptane-3,5-diol diacetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102208062D          

 39 40  0  0  1  0            999 V2000
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3 37  1  0  0  0  0
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 38 39  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309102208062D          

 39 40  0  0  1  0            999 V2000
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    2.8579   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 13 24  1  0  0  0  0
 10 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
  8 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
  5 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  2  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296498

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CC[C@@H](C[C@H](CCC2=CC(OC)=C(OC)C(OC)=C2)OC(C)=O)OC(C)=O)=CC(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O10/c1-18(30)38-22(11-9-20-13-24(32-3)28(36-7)25(14-20)33-4)17-23(39-19(2)31)12-10-21-15-26(34-5)29(37-8)27(16-21)35-6/h13-16,22-23H,9-12,17H2,1-8H3/t22-,23-/m0/s1

> <INCHI_KEY>
CGTJVLRFIFOYEN-GOTSBHOMSA-N

> <FORMULA>
C29H40O10

> <MOLECULAR_WEIGHT>
548.629

> <EXACT_MASS>
548.262147488

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
59.863870012687954

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,5S)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate

> <JCHEM_LOGP>
3.8224439996666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.143613248038233

> <JCHEM_POLAR_SURFACE_AREA>
107.98000000000002

> <JCHEM_REFRACTIVITY>
143.77879999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,5S)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.668   0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.003   0.770   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   25                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   13                                                       
CONECT   25   10   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    8   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    5   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   34    3   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

View in JSmol

Synonyms

Value	Source
(3S,5S)-1,7-Bis(3,4,5-trimethoxyphenyl)heptane-3,5-diol diacetic acid	Generator

Chemical Formula

C₂₉H₄₀O₁₀

Average Mass

548.6290 Da

Monoisotopic Mass

548.26215 Da

IUPAC Name

(3S,5S)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate

Traditional Name

(3S,5S)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(CC[C@@H](C[C@H](CCC2=CC(OC)=C(OC)C(OC)=C2)OC(C)=O)OC(C)=O)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C29H40O10/c1-18(30)38-22(11-9-20-13-24(32-3)28(36-7)25(14-20)33-4)17-23(39-19(2)31)12-10-21-15-26(34-5)29(37-8)27(16-21)35-6/h13-16,22-23H,9-12,17H2,1-8H3/t22-,23-/m0/s1

InChI Key

CGTJVLRFIFOYEN-GOTSBHOMSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Curcuminoids

Alternative Parents

Substituents

Curcumin
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Ether
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	3.82	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	107.98 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	143.78 m³·mol⁻¹	ChemAxon
Polarizability	59.86 Å³	ChemAxon
Number of Rings	2	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

28288638

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57343250

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,5s)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate (NP0296498)

MOL for NP0296498 ((3s,5s)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate)

3D MOL for NP0296498 ((3s,5s)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate)

3D SDF for NP0296498 ((3s,5s)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate)

3D-SDF for NP0296498 ((3s,5s)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate)

PDB for NP0296498 ((3s,5s)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate)

3D PDB for NP0296498 ((3s,5s)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate)

SMILES for NP0296498 ((3s,5s)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate)

INCHI for NP0296498 ((3s,5s)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate)

Structure for NP0296498 ((3s,5s)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate)

3D Structure for NP0296498 ((3s,5s)-5-(acetyloxy)-1,7-bis(3,4,5-trimethoxyphenyl)heptan-3-yl acetate)