NP-MRD: Showing NP-Card for (1e,6e)-1-{3-[(2e)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione (NP0181124)

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Record Information

Version

2.0

Created at

2022-09-03 19:35:37 UTC

Updated at

2022-09-03 19:35:37 UTC

NP-MRD ID

NP0181124

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1e,6e)-1-{3-[(2e)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

Description

Cassumunin C 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. (1e,6e)-1-{3-[(2e)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione is found in Zingiber montanum. Based on a literature review very few articles have been published on Cassumunin C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032221352D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309032221352D          

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   11.4315   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
  5 14  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  2  0  0  0  0
 27 35  1  0  0  0  0
 17 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 37 40  2  0  0  0  0
 15 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0181124

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C(=C2)C(\C=C\C)C2=CC=C(OC)C(OC)=C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C33H34O8/c1-6-7-26(23-11-15-29(38-2)31(19-23)40-4)27-16-22(18-32(41-5)33(27)37)9-13-25(35)20-24(34)12-8-21-10-14-28(36)30(17-21)39-3/h6-19,26,36-37H,20H2,1-5H3/b7-6+,12-8+,13-9+

> <INCHI_KEY>
VTDIEUQNUUTRAF-BRLOHPTNSA-N

> <FORMULA>
C33H34O8

> <MOLECULAR_WEIGHT>
558.627

> <EXACT_MASS>
558.225368055

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
59.8168072758509

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1E,6E)-1-{3-[(2E)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

> <JCHEM_LOGP>
6.715210816333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.494865751030643

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.951513330537018

> <JCHEM_PKA_STRONGEST_BASIC>
-4.219526803688985

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000001

> <JCHEM_REFRACTIVITY>
161.34139999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1E,6E)-1-{3-[(2E)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.669 -18.480   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.336 -19.250   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002 -16.940   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      17.338  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.672  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.005   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      21.339   1.540   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      22.673   2.310   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      21.339  -0.000   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      22.673  -0.770   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      22.673  -2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      20.005  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      16.004 -12.320   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      13.337 -13.860   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11    5                                                       
CONECT   15    4   16   40                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   36                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   35                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   27                                                       
CONECT   36   17   37                                                       
CONECT   37   36   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   37   15   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₄O₈

Average Mass

558.6270 Da

Monoisotopic Mass

558.22537 Da

IUPAC Name

(1E,6E)-1-{3-[(2E)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

Traditional Name

(1E,6E)-1-{3-[(2E)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C(=C2)C(\C=C\C)C2=CC=C(OC)C(OC)=C2)=CC=C1O

InChI Identifier

InChI=1S/C33H34O8/c1-6-7-26(23-11-15-29(38-2)31(19-23)40-4)27-16-22(18-32(41-5)33(27)37)9-13-25(35)20-24(34)12-8-21-10-14-28(36)30(17-21)39-3/h6-19,26,36-37H,20H2,1-5H3/b7-6+,12-8+,13-9+

InChI Key

VTDIEUQNUUTRAF-BRLOHPTNSA-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
Zingiber montanum	LOTUS Database	35616633

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
Diphenylmethane
Cinnamic acid or derivatives
Hydroxycinnamic acid or derivatives
Methoxyphenol
Dimethoxybenzene
O-dimethoxybenzene
Phenoxy compound
Anisole
Styrene
Phenol ether
Methoxybenzene
Alkyl aryl ether
1,3-diketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
1,3-dicarbonyl compound
Enone
Alpha,beta-unsaturated ketone
Acryloyl-group
Ketone
Ether
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
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	6.72	ChemAxon
pKa (Strongest Acidic)	8.95	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.52 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	161.34 m³·mol⁻¹	ChemAxon
Polarizability	59.82 Å³	ChemAxon
Number of Rings	3	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

8160810

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9985220

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1e,6e)-1-{3-[(2e)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione (NP0181124)

MOL for NP0181124 ((1e,6e)-1-{3-[(2e)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione)

3D MOL for NP0181124 ((1e,6e)-1-{3-[(2e)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione)

3D SDF for NP0181124 ((1e,6e)-1-{3-[(2e)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione)

3D-SDF for NP0181124 ((1e,6e)-1-{3-[(2e)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione)

PDB for NP0181124 ((1e,6e)-1-{3-[(2e)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione)

3D PDB for NP0181124 ((1e,6e)-1-{3-[(2e)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione)

SMILES for NP0181124 ((1e,6e)-1-{3-[(2e)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione)

INCHI for NP0181124 ((1e,6e)-1-{3-[(2e)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione)

Structure for NP0181124 ((1e,6e)-1-{3-[(2e)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione)

3D Structure for NP0181124 ((1e,6e)-1-{3-[(2e)-1-(3,4-dimethoxyphenyl)but-2-en-1-yl]-4-hydroxy-5-methoxyphenyl}-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione)