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Showing NP-Card for Curcumin III (NP0337939)

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Record Information
Version2.0
Created at2024-09-11 13:08:07 UTC
Updated at2024-09-11 13:08:07 UTC
NP-MRD IDNP0337939
Secondary Accession NumbersNone
Natural Product Identification
Common NameCurcumin III
DescriptionCurcumin III belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Curcumin III is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Curcumin III has been detected, but not quantified in, herbs and spices. This could make curcumin III a potential biomarker for the consumption of these foods. All three of the curcuminoids found in Curcuma longa have been shown to have antioxidant properties, but bisdemethoxycurcumin is more resistant than the others to alkaline degradation. Bisdemethoxycurcumin is used as a pigment and Nutraceutical with antimutagenic properties. Bisdemethoxycurcumin is a curcuminoid found (along with the curcuminoids curcumin and demethoxycurcumin) in turmeric (Curcuma longa), but absent in Javanese turmeric (Curcuma xanthorrhiza).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337939 (Curcumin III)


  Mrv0541 05061311162D          

 25 26  0  0  0  0            999 V2000
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    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
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    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
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  2  0  0  0  0
  6  2  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 16  3  1  0  0  0  0
 16  7  2  0  0  0  0
 16  8  1  0  0  0  0
 17  4  1  0  0  0  0
 17  9  2  0  0  0  0
 17 10  1  0  0  0  0
 18 11  2  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
 19 14  1  0  0  0  0
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 20 15  1  0  0  0  0
 21  6  1  0  0  0  0
 21 15  1  0  0  0  0
 22 18  1  0  0  0  0
 23 19  1  0  0  0  0
 24 20  2  0  0  0  0
 25 21  2  0  0  0  0
M  END
Download

3D MOL for NP0337939 (Curcumin III)

Download
3D SDF for NP0337939 (Curcumin III)

  Mrv0541 05061311162D          

 25 26  0  0  0  0            999 V2000
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    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
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    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
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  2  0  0  0  0
  6  2  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 16  3  1  0  0  0  0
 16  7  2  0  0  0  0
 16  8  1  0  0  0  0
 17  4  1  0  0  0  0
 17  9  2  0  0  0  0
 17 10  1  0  0  0  0
 18 11  2  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
 19 14  1  0  0  0  0
 20  5  1  0  0  0  0
 20 15  1  0  0  0  0
 21  6  1  0  0  0  0
 21 15  1  0  0  0  0
 22 18  1  0  0  0  0
 23 19  1  0  0  0  0
 24 20  2  0  0  0  0
 25 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0337939

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C\C=C\C(=O)CC(=O)\C=C/CC2=CC=C(O)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O4/c22-18-11-7-16(8-12-18)3-1-5-20(24)15-21(25)6-2-4-17-9-13-19(23)14-10-17/h1-2,5-14,22-23H,3-4,15H2/b5-1-,6-2+

> <INCHI_KEY>
YIKBSQXTKGFYHB-SOSXVSKCSA-N

> <FORMULA>
C21H20O4

> <MOLECULAR_WEIGHT>
336.3811

> <EXACT_MASS>
336.136159128

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.895745275445336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,7E)-1,9-bis(4-hydroxyphenyl)nona-2,7-diene-4,6-dione

> <ALOGPS_LOGP>
4.25

> <JCHEM_LOGP>
5.163604412333333

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.511347437573953

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.034005950767206

> <JCHEM_PKA_STRONGEST_BASIC>
-4.744174782492015

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
100.08619999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,7E)-1,9-bis(4-hydroxyphenyl)nona-2,7-diene-4,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0337939 (Curcumin III)
Download
PDB for NP0337939 (Curcumin III)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   2.310   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      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   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      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -8.002  10.780   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1   16                                                       
CONECT    4    2   17                                                       
CONECT    5    1   20                                                       
CONECT    6    2   21                                                       
CONECT    7   11   16                                                       
CONECT    8   12   16                                                       
CONECT    9   13   17                                                       
CONECT   10   14   17                                                       
CONECT   11    7   18                                                       
CONECT   12    8   18                                                       
CONECT   13    9   19                                                       
CONECT   14   10   19                                                       
CONECT   15   20   21                                                       
CONECT   16    3    7    8                                                  
CONECT   17    4    9   10                                                  
CONECT   18   11   12   22                                                  
CONECT   19   13   14   23                                                  
CONECT   20    5   15   24                                                  
CONECT   21    6   15   25                                                  
CONECT   22   18                                                            
CONECT   23   19                                                            
CONECT   24   20                                                            
CONECT   25   21                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

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3D PDB for NP0337939 (Curcumin III)
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SMILES for NP0337939 (Curcumin III)
OC1=CC=C(C\C=C\C(=O)CC(=O)\C=C/CC2=CC=C(O)C=C2)C=C1
Download
INCHI for NP0337939 (Curcumin III)
InChI=1S/C21H20O4/c22-18-11-7-16(8-12-18)3-1-5-20(24)15-21(25)6-2-4-17-9-13-19(23)14-10-17/h1-2,5-14,22-23H,3-4,15H2/b5-1-,6-2+
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View in JSmol
Synonyms
ValueSource
1,9-Bis(4-hydroxyphenyl)-2,7-nonadiene-4,6-dioneHMDB
1,9-Bis(4-hydroxyphenyl)-2,7-nonadiene-4,6-dione, 9ciHMDB
Chemical FormulaC21H20O4
Average Mass336.3811 Da
Monoisotopic Mass336.13616 Da
IUPAC Name(2Z,7E)-1,9-bis(4-hydroxyphenyl)nona-2,7-diene-4,6-dione
Traditional Name(2Z,7E)-1,9-bis(4-hydroxyphenyl)nona-2,7-diene-4,6-dione
CAS Registry NumberNot Available
SMILES
OC1=CC=C(C\C=C\C(=O)CC(=O)\C=C/CC2=CC=C(O)C=C2)C=C1
InChI Identifier
InChI=1S/C21H20O4/c22-18-11-7-16(8-12-18)3-1-5-20(24)15-21(25)6-2-4-17-9-13-19(23)14-10-17/h1-2,5-14,22-23H,3-4,15H2/b5-1-,6-2+
InChI KeyYIKBSQXTKGFYHB-SOSXVSKCSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub Class1-hydroxy-2-unsubstituted benzenoids  
Direct Parent1-hydroxy-2-unsubstituted benzenoids  
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • 1,3-diketone
    • 

  • 1,3-dicarbonyl compound
    • 

  • Monocyclic benzene moiety
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Enone
    • 

  • Acryloyl-group
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.25ALOGPS
logP5.16ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)9.03ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity100.09 m³·mol⁻¹ChemAxon
Polarizability36.9 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0039609  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019236  
KNApSAcK IDNot Available
Chemspider ID30777356  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBisdemethoxycurcumin  
METLIN IDNot Available
PubChem Compound131752689  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available