NP-MRD: Showing NP-Card for 1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione (NP0217277)

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Record Information

Version

2.0

Created at

2022-09-05 17:34:42 UTC

Updated at

2022-09-05 17:34:43 UTC

NP-MRD ID

NP0217277

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione

Description

[10]-Gingerdione belongs to the class of organic compounds known as gingerdiones. Gingerdiones are compounds containing a gingerdione moiety, which is structurally characterized by a 4-hydroxy-3-methoxyphenyl group substituted at the C6 carbon atom by an alkane-2,4-dione. [10]-Gingerdione is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, [10]-Gingerdione has been detected, but not quantified in, herbs and spices. 1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione is found in Zingiber officinale. This could make [10]-gingerdione a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061304472D          

 25 25  0  0  0  0            999 V2000
  -10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    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
   -4.2868    0.8250    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
    0.0000    0.0000    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
    0.7145   -0.4125    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
   -2.8579    0.8250    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
   -3.5724    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
    1.4289    0.0000    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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    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
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  2  0  0  0  0
 17 11  1  0  0  0  0
 17 12  1  0  0  0  0
 17 15  2  0  0  0  0
 18 10  1  0  0  0  0
 18 16  1  0  0  0  0
 19 13  1  0  0  0  0
 19 16  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 21 20  2  0  0  0  0
 22 18  2  0  0  0  0
 23 19  2  0  0  0  0
 24 20  1  0  0  0  0
 25  2  1  0  0  0  0
 25 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217277

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCC(=O)CC(=O)CCC1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O4/c1-3-4-5-6-7-8-9-10-18(22)16-19(23)13-11-17-12-14-20(24)21(15-17)25-2/h12,14-15,24H,3-11,13,16H2,1-2H3

> <INCHI_KEY>
QPSYZJDGMPQMSV-UHFFFAOYSA-N

> <FORMULA>
C21H32O4

> <MOLECULAR_WEIGHT>
348.4764

> <EXACT_MASS>
348.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
41.57442254442802

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione

> <ALOGPS_LOGP>
5.60

> <JCHEM_LOGP>
5.9583221763333345

> <ALOGPS_LOGS>
-4.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.968858372768874

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.656764134296806

> <JCHEM_PKA_STRONGEST_BASIC>
-4.889948023656134

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
100.69089999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.17e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

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     -18.672   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -17.338   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -16.004   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -14.671   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335   1.540   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      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   25                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   18                                                       
CONECT   11   13   17                                                       
CONECT   12   14   17                                                       
CONECT   13   11   19                                                       
CONECT   14   12   20                                                       
CONECT   15   17   21                                                       
CONECT   16   18   19                                                       
CONECT   17   11   12   15                                                  
CONECT   18   10   16   22                                                  
CONECT   19   13   16   23                                                  
CONECT   20   14   21   24                                                  
CONECT   21   15   20   25                                                  
CONECT   22   18                                                            
CONECT   23   19                                                            
CONECT   24   20                                                            
CONECT   25    2   21                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Value	Source
1-(4-Hydroxy-3-methoxyphenyl)-3,5-tetradecanedione	HMDB

Chemical Formula

C₂₁H₃₂O₄

Average Mass

348.4764 Da

Monoisotopic Mass

348.23006 Da

IUPAC Name

1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione

Traditional Name

1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione

CAS Registry Number

Not Available

SMILES

CCCCCCCCCC(=O)CC(=O)CCC1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C21H32O4/c1-3-4-5-6-7-8-9-10-18(22)16-19(23)13-11-17-12-14-20(24)21(15-17)25-2/h12,14-15,24H,3-11,13,16H2,1-2H3

InChI Key

QPSYZJDGMPQMSV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Zingiber officinale	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gingerdiones. Gingerdiones are compounds containing a gingerdione moiety, which is structurally characterized by a 4-hydroxy-3-methoxyphenyl group substituted at the C6 carbon atom by an alkane-2,4-dione.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Gingerdione
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1,3-diketone
Monocyclic benzene moiety
1,3-dicarbonyl compound
Ketone
Ether
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	5.6	ALOGPS
logP	5.96	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	8.66	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	100.69 m³·mol⁻¹	ChemAxon
Polarizability	41.57 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029475

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000598

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14440539

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione (NP0217277)

MOL for NP0217277 (1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione)

3D MOL for NP0217277 (1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione)

3D SDF for NP0217277 (1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione)

3D-SDF for NP0217277 (1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione)

PDB for NP0217277 (1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione)

3D PDB for NP0217277 (1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione)

SMILES for NP0217277 (1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione)

INCHI for NP0217277 (1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione)

Structure for NP0217277 (1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione)

3D Structure for NP0217277 (1-(4-hydroxy-3-methoxyphenyl)tetradecane-3,5-dione)