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Showing NP-Card for Curzerenone (NP0048469)

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Record Information
Version2.0
Created at2022-03-17 20:56:57 UTC
Updated at2022-03-17 20:56:57 UTC
NP-MRD IDNP0048469
Secondary Accession NumbersNone
Natural Product Identification
Common NameCurzerenone
DescriptionCurzerenone, also known as zedoarone, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Curzerenone is an extremely weak basic (essentially neutral) compound (based on its pKa). Curzerenone is an antimicrobial isolate of Lindera pulcherrima. Outside of the human body, Curzerenone has been detected, but not quantified in, turmerics. Curzerenone is found in Commiphora gileadensis, Commiphora myrrha, Commiphora opobalsamum , Commiphora sphaerocarpa, Commiphora wightii, Curcuma aeruginosa , Curcuma amanda Roxb, Curcuma aromatica , Curcuma xanthorrhiza , Curcuma zedoaria and Prumnopitys andina. This could make curzerenone a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0048469 (Curzerenone)


  Mrv0541 05061308542D          

 17 18  0  0  0  0            999 V2000
    4.6951    0.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6345    0.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648   -0.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  9  2  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  2  0  0  0  0
 11  7  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13  9  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  5  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17  8  1  0  0  0  0
 17 11  1  0  0  0  0
M  END
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3D MOL for NP0048469 (Curzerenone)

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3D SDF for NP0048469 (Curzerenone)

  Mrv0541 05061308542D          

 17 18  0  0  0  0            999 V2000
    4.6951    0.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6345    0.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648   -0.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  9  2  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  2  0  0  0  0
 11  7  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13  9  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  5  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17  8  1  0  0  0  0
 17 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048469

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1C(=O)C2=C(CC1(C)C=C)OC=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O2/c1-6-15(5)7-11-12(10(4)8-17-11)14(16)13(15)9(2)3/h6,8,13H,1-2,7H2,3-5H3

> <INCHI_KEY>
ZVMJXSJCBLRAPD-UHFFFAOYSA-N

> <FORMULA>
C15H18O2

> <MOLECULAR_WEIGHT>
230.3022

> <EXACT_MASS>
230.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.990784828530842

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-4,5,6,7-tetrahydro-1-benzofuran-4-one

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
3.3534603653333335

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.612283172663727

> <JCHEM_PKA_STRONGEST_BASIC>
-3.516580417203723

> <JCHEM_POLAR_SURFACE_AREA>
30.21

> <JCHEM_REFRACTIVITY>
69.0832

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-1-benzofuran-4-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048469 (Curzerenone)
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PDB for NP0048469 (Curzerenone)
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       8.764   0.379   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.784   0.914   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.774  -0.800   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4   10                                                            
CONECT    5   15                                                            
CONECT    6    1   15                                                       
CONECT    7   11   15                                                       
CONECT    8   10   17                                                       
CONECT    9    2    3   13                                                  
CONECT   10    4    8   12                                                  
CONECT   11    7   12   17                                                  
CONECT   12   10   11   14                                                  
CONECT   13    9   14   15                                                  
CONECT   14   12   13   16                                                  
CONECT   15    5    6    7   13                                             
CONECT   16   14                                                            
CONECT   17    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

Download
3D PDB for NP0048469 (Curzerenone)
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SMILES for NP0048469 (Curzerenone)
CC(=C)C1C(=O)C2=C(CC1(C)C=C)OC=C2C
Download
INCHI for NP0048469 (Curzerenone)
InChI=1S/C15H18O2/c1-6-15(5)7-11-12(10(4)8-17-11)14(16)13(15)9(2)3/h6,8,13H,1-2,7H2,3-5H3
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View in JSmol
Synonyms
ValueSource
ZedoaroneHMDB
Chemical FormulaC15H18O2
Average Mass230.3022 Da
Monoisotopic Mass230.13068 Da
IUPAC Name6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-4,5,6,7-tetrahydro-1-benzofuran-4-one
Traditional Name6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-1-benzofuran-4-one
CAS Registry Number20493-56-5
SMILES
CC(=C)C1C(=O)C2=C(CC1(C)C=C)OC=C2C
InChI Identifier
InChI=1S/C15H18O2/c1-6-15(5)7-11-12(10(4)8-17-11)14(16)13(15)9(2)3/h6,8,13H,1-2,7H2,3-5H3
InChI KeyZVMJXSJCBLRAPD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Commiphora gileadensisLOTUS Database
Commiphora myrrhaLOTUS Database
Commiphora opobalsamumPlant
Commiphora sphaerocarpaLOTUS Database
Commiphora wightiiLOTUS Database
Curcuma aeruginosaPlant
Curcuma amanda RoxbPlant
Curcuma aromaticaPlant
Curcuma longaFooDB
Curcuma xanthorrhizaPlant
Curcuma zedoariaPlant
Prumnopitys andinaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentAromatic monoterpenoids  
Alternative Parents
Substituents
  • Menthofuran monoterpenoid
    • 

  • Aromatic monoterpenoid
    • 

  • Bicyclic monoterpenoid
    • 

  • Benzofuran
    • 

  • Aryl ketone
    • 

  • Aryl alkyl ketone
    • 

  • Furan
    • 

  • Heteroaromatic compound
    • 

  • Ketone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP3.6ALOGPS
logP3.35ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)18.61ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area30.21 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.08 m³·mol⁻¹ChemAxon
Polarizability25.99 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036155  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015007  
KNApSAcK IDNot Available
Chemspider ID4474745  
KEGG Compound IDC16943  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCurzerenone  
METLIN IDNot Available
PubChem Compound5315433  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References