NP-MRD: Showing NP-Card for Curcumenol (NP0047799)

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Record Information

Version

2.0

Created at

2022-03-17 20:46:10 UTC

Updated at

2022-03-17 20:46:10 UTC

NP-MRD ID

NP0047799

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Curcumenol

Description

Curcumenol belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. Curcumenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, curcumenol has been detected, but not quantified in, herbs and spices. This could make curcumenol a potential biomarker for the consumption of these foods. Curcumenol is found in Foeniculum vulgare , Curcuma aeruginosa , Curcuma harmandii, Curcuma heyneana, Curcuma kwangsiensis , Curcuma phaecaulis, Curcuma phaeocaulis, Curcuma wenyujin , Curcuma zedoaria , Houttuynia cordata , Houttuynia emeiensis, Tabernaemontana catharinensis and Zanthoxylum armatum . 4-Epicurcumenol is a constituent of rhizomes of Curcuma zedoaria (zedoary).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241208342D          

 17 19  0  0  0  0            999 V2000
    1.6619    0.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3115   -0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -0.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2245   -1.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249   -1.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249   -0.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2616   -0.3498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3497    0.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5238    0.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4867    1.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6989    1.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0865    2.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5238   -2.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486   -1.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9612   -0.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9612    0.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7489    0.2616    0.0000 O   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
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 14  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 16  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  2  0  0  0  0
  9 16  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047799

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2C(C)=CC3(O)OC12CC3=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h7,11-12,16H,5-6,8H2,1-4H3

> <INCHI_KEY>
ISFMXVMWEWLJGJ-UHFFFAOYSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.219032823604312

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol

> <ALOGPS_LOGP>
2.52

> <JCHEM_LOGP>
3.1425060316666666

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.085590991152896

> <JCHEM_PKA_STRONGEST_BASIC>
-4.435632702004688

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
69.17859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.102   1.140   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.448  -0.163   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.265  -1.467   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.286  -2.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.980  -2.121   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.980  -0.488   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.488  -0.653   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.653   1.140   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.978   1.467   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.775   3.592   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.305   2.938   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.161   4.081   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.978  -4.081   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.651  -2.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.794  -1.467   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.794   0.161   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.265   0.488   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    2    5    7    8                                             
CONECT    7    6   16                                                       
CONECT    8    6    9                                                       
CONECT    9    8   11   16                                                  
CONECT   10   11                                                            
CONECT   11    9   10   12                                                  
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14    5   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16    7    9   15   17                                             
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₂

Average Mass

234.3340 Da

Monoisotopic Mass

234.16198 Da

IUPAC Name

2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol

Traditional Name

2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol

CAS Registry Number

19431-84-6

SMILES

CC1CCC2C(C)=CC3(O)OC12CC3=C(C)C

InChI Identifier

InChI=1S/C15H22O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h7,11-12,16H,5-6,8H2,1-4H3

InChI Key

ISFMXVMWEWLJGJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anethum foeniculum	Plant	KNApSAcK
Curcuma aeruginosa	Plant	KNApSAcK
Curcuma harmandii	LOTUS Database	35616633
Curcuma heyneana	LOTUS Database	35616633
Curcuma kwangsiensis	Plant	KNApSAcK
Curcuma longa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Curcuma phaecaulis	Plant	KNApSAcK
Curcuma phaeocaulis	LOTUS Database	35616633
Curcuma wenyujin	Plant	KNApSAcK
Curcuma zedoaria	Plant	KNApSAcK
Houttuynia cordata	Plant	KNApSAcK
Houttuynia emeiensis	Plant	KNApSAcK
Tabernaemontana catharinensis	Plant	KNApSAcK
Zanthoxylum armatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Guaianes

Alternative Parents

Substituents

Guaiane sesquiterpenoid
Pyran
Tetrahydrofuran
Hemiacetal
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sesquiterpenoid (CHEBI:80811 )

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	2.52	ALOGPS
logP	3.14	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.09	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.18 m³·mol⁻¹	ChemAxon
Polarizability	27.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon