NP-MRD: Showing NP-Card for Bisdemethoxycurcumin (NP0044151)

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Record Information

Version

1.0

Created at

2021-11-12 23:53:00 UTC

Updated at

2021-11-26 17:46:00 UTC

NP-MRD ID

NP0044151

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bisdemethoxycurcumin

Description

Bisdemethoxycurcumin is found in Alpinia roxburghii, Curcuma aromatica , Curcuma mangga , Curcuma picta, Curcuma zedoaria and Zingiber officinale . It was first documented in 2005 (L.Péret-Almeida et al.).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.2293   -1.4275    3.0329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7660   -0.8920    2.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0925   -0.4896    0.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4012   -0.6696    0.9794 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9838   -1.2629    2.0889 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2451   -0.2535   -0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5480   -0.4351   -0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4681   -0.0509   -1.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0697    0.5492   -2.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0108    0.8759   -3.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3520    0.6310   -3.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3174    0.9523   -4.0652 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7318    0.0245   -1.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8277   -0.3212   -0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2059   -0.7042    2.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799   -0.1615    1.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3324    0.0271    1.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1557   -0.3566    2.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5341   -0.1471    1.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1125    0.4415    0.8897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4642    0.6512    0.8044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2967    0.8268   -0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9431    0.6203   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3392   -0.0270    0.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0522   -0.8523    2.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7942    0.1994   -0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9357   -0.9124    0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0207    0.7458   -2.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6621    1.3454   -4.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7827    1.8436   -4.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7970   -0.1712   -1.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1519   -0.7912   -0.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7691   -1.0408    2.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3314    0.1729    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7269   -0.8215    2.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1715   -0.4512    2.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9328    1.4809    1.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7591    1.2980   -1.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2946    0.9179   -0.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  4  5  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 14  8  1  0
 23 17  1  0
  3 24  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
  5 25  1  0
 15 33  1  0
 16 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
 22 38  1  0
 23 39  1  0
M  END


  Mrv1652311132100532D          

 23 24  0  0  0  0            999 V2000
    3.5724    1.2375    0.0000 O   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
    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 C   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   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  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  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
  4 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 17 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044151

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O\C(\C=C\C1=CC=C(O)C=C1)=C/C(=O)/C=C/C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-13,20-22H/b11-5+,12-6+,18-13-

> <INCHI_KEY>
YXAKCQIIROBKOP-HSSGTREWSA-N

> <FORMULA>
C19H16O4

> <MOLECULAR_WEIGHT>
308.3279

> <EXACT_MASS>
308.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
33.37945831229191

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
4.074381888

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.156857958129207

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.64189766639493

> <JCHEM_PKA_STRONGEST_BASIC>
-5.290946247828647

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
93.1999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      14.670   6.930   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
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   13                                                       
CONECT   13   12    7                                                       
CONECT   14    4                                                            
CONECT   15    2   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₆O₄

Average Mass

308.3279 Da

Monoisotopic Mass

308.10486 Da

IUPAC Name

(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one

Traditional Name

(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one

CAS Registry Number

Not Available

SMILES

O\C(\C=C\C1=CC=C(O)C=C1)=C/C(=O)/C=C/C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-13,20-22H/b11-5+,12-6+,18-13-

InChI Key

YXAKCQIIROBKOP-HSSGTREWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alpinia roxburghii	LOTUS Database	35616633
Curcuma aromatica	Plant	KNApSAcK
Curcuma longa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Curcuma mangga	Plant	KNApSAcK
Curcuma picta	LOTUS Database	35616633
Curcuma zedoaria	Plant	KNApSAcK
Zingiber officinale	Plant	KNApSAcK

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

Bis-desmethoxycurcumin
Hydroxycinnamic acid or derivatives
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Enone
Vinylogous acid
Alpha,beta-unsaturated ketone
Ketone
Enol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	3.5	ALOGPS
logP	4.07	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	8.64	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.2 m³·mol⁻¹	ChemAxon
Polarizability	33.38 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

FDB011961

KNApSAcK ID

C00032769

Chemspider ID

Not Available

KEGG Compound ID

C17743

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bisdemethoxycurcumin

METLIN ID

Not Available

PubChem Compound

5324473

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

L.Péret-Almeida et al. (2005). Separation and determination of the physico-chemical characteristics of curcumin, demethoxycurcumin and bisdemethoxycurcumin. Food Research International, Volume 38, Issues 8–9, October–November 2005, Pages 1039-1044. DOI: 10.1016/j.foodres.2005.02.021. Food Research International.

Showing NP-Card for Bisdemethoxycurcumin (NP0044151)

MOL for NP0044151 (Bisdemethoxycurcumin)

3D MOL for NP0044151 (Bisdemethoxycurcumin)

3D SDF for NP0044151 (Bisdemethoxycurcumin)

3D-SDF for NP0044151 (Bisdemethoxycurcumin)

PDB for NP0044151 (Bisdemethoxycurcumin)

3D PDB for NP0044151 (Bisdemethoxycurcumin)

SMILES for NP0044151 (Bisdemethoxycurcumin)

INCHI for NP0044151 (Bisdemethoxycurcumin)

Structure for NP0044151 (Bisdemethoxycurcumin)

3D Structure for NP0044151 (Bisdemethoxycurcumin)