NP-MRD: Showing NP-Card for Procurcumenol (NP0048501)

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Record Information

Version

2.0

Created at

2022-03-17 20:57:27 UTC

Updated at

2022-03-17 20:57:28 UTC

NP-MRD ID

NP0048501

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Procurcumenol

Description

Procurcumenol 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. Procurcumenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Procurcumenol has been detected, but not quantified in, herbs and spices and turmerics. Procurcumenol is found in Curcuma aromatica, Curcuma heyneana, Curcuma phaeocaulis and Curcuma zedoaria . This could make procurcumenol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309082D          

 17 18  0  0  0  0            999 V2000
    5.4871   -1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699   -2.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690    1.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2585   -1.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713   -1.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -0.2055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2085   -1.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 14 12  1  0  0  0  0
 15  4  1  0  0  0  0
 15  6  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048501

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C1CC2C(CCC2(C)O)C(C)=CC1=O

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

> <INCHI_KEY>
RHBOHEXDGUVIIY-UHFFFAOYSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.19261406602455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-3,8-dimethyl-5-(propan-2-ylidene)-1,2,3,3a,4,5,6,8a-octahydroazulen-6-one

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.7819444329999996

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.866575191253638

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.694200674738095

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6699935865499987

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
70.68379999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-1,4-dimethyl-7-(propan-2-ylidene)-3,3a,8,8a-tetrahydro-2H-azulen-6-one

> <JCHEM_VEBER_RULE>
1

$$$$

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      10.243  -2.745   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.157  -4.409   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.915   2.848   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.216  -3.036   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.720  -2.975   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.760  -1.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590  -1.629   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.968  -0.384   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.256  -2.399   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   15                                                            
CONECT    5    6   11                                                       
CONECT    6    5   15                                                       
CONECT    7   10   14                                                       
CONECT    8   12   13                                                       
CONECT    9    1    2   12                                                  
CONECT   10    3    7   11                                                  
CONECT   11    5   10   13                                                  
CONECT   12    8    9   14                                                  
CONECT   13    8   11   15                                                  
CONECT   14    7   12   16                                                  
CONECT   15    4    6   13   17                                             
CONECT   16   14                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
Epiprocurcumenol	MeSH

Chemical Formula

C₁₅H₂₂O₂

Average Mass

234.3340 Da

Monoisotopic Mass

234.16198 Da

IUPAC Name

3-hydroxy-3,8-dimethyl-5-(propan-2-ylidene)-1,2,3,3a,4,5,6,8a-octahydroazulen-6-one

Traditional Name

1-hydroxy-1,4-dimethyl-7-(propan-2-ylidene)-3,3a,8,8a-tetrahydro-2H-azulen-6-one

CAS Registry Number

21698-40-8

SMILES

CC(C)=C1CC2C(CCC2(C)O)C(C)=CC1=O

InChI Identifier

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

InChI Key

RHBOHEXDGUVIIY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Curcuma aromatica	LOTUS Database	35616633
Curcuma heyneana	LOTUS Database	35616633
Curcuma longa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Curcuma phaeocaulis	LOTUS Database	35616633
Curcuma zedoaria	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
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.4	ALOGPS
logP	2.78	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	18.69	ChemAxon
pKa (Strongest Basic)	-0.67	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.68 m³·mol⁻¹	ChemAxon
Polarizability	27.19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036427

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015314

KNApSAcK ID

C00020416

Chemspider ID

4478722

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320710

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Procurcumenol (NP0048501)

MOL for NP0048501 (Procurcumenol)

3D MOL for NP0048501 (Procurcumenol)

3D SDF for NP0048501 (Procurcumenol)

3D-SDF for NP0048501 (Procurcumenol)

PDB for NP0048501 (Procurcumenol)

3D PDB for NP0048501 (Procurcumenol)

SMILES for NP0048501 (Procurcumenol)

INCHI for NP0048501 (Procurcumenol)

Structure for NP0048501 (Procurcumenol)

3D Structure for NP0048501 (Procurcumenol)