NP-MRD: Showing NP-Card for Cohulupone (NP0085779)

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Record Information

Version

2.0

Created at

2022-04-29 06:14:58 UTC

Updated at

2022-04-29 06:14:58 UTC

NP-MRD ID

NP0085779

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cohulupone

Description

Cohulupone belongs to the class of organic compounds known as beta-diketones. These are organic compounds containing two keto groups separated by a single carbon atom. Cohulupone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Cohulupone has been detected, but not quantified in, alcoholic beverages. Cohulupone is found in Garcinia subelliptica. This could make cohulupone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 49 49  0  0  0  0  0  0  0  0999 V2000
   -1.2259    3.8904   -1.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9248    3.8298    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2971    5.0006    0.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2072    2.7637    0.7189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8266    1.6028    0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0379    0.3185    0.2278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7941   -0.7092   -0.5980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1600   -2.0204   -0.6540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8104   -3.0989   -0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2017   -2.9767    0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2079   -4.4669   -0.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8594   -0.0635    1.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6416   -0.6716    2.3984 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4632    0.4068    2.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552    0.7824    3.1669 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029    0.3645    0.8134 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1054   -0.8775    0.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0398   -1.7245    1.5790 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0126   -1.1011   -0.4319 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7397   -2.4024   -0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0068    0.0344   -0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3410    0.5195   -0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5776    0.7765   -1.4627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0914    4.9157   -1.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6986    3.1241   -1.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3272    3.6870   -1.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8105    4.9253    0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5459    5.9569    0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140    5.1227    1.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9870    2.7255    1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8642    1.4098    0.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9003    1.7742   -1.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7846   -0.8034   -0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9814   -0.2482   -1.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1373   -2.1786   -1.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3381   -2.3546    1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8024   -2.4950   -0.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6895   -3.9872    0.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9279   -5.1274   -0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422   -4.8911    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607   -4.4968   -0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0194    1.2105    0.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3678   -1.1314   -1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7788   -2.2557   -0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8170   -2.7659    0.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2992   -3.1788   -1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4870    0.8794   -1.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8246   -0.2729   -1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4387    0.2790    0.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 21  1  0
 19 17  1  0
 17 18  2  0
 17 16  1  0
 16 14  1  0
 14 15  2  0
 14 12  1  0
 12 13  2  0
 12  6  1  0
  6  5  1  1
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
  6 22  1  0
 22 23  2  0
 22 16  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 19 43  1  6
 21 47  1  0
 21 48  1  0
 21 49  1  0
 16 42  1  1
  5 31  1  0
  5 32  1  0
  4 30  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
M  END


  Mrv0541 05061304592D          

 23 23  0  0  0  0            999 V2000
   -2.1503    1.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0883    2.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2858    1.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2239    2.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -1.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857    0.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912    1.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9268    1.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3433    2.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4788    2.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 12  3  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  2  0  0  0  0
 13  5  1  0  0  0  0
 13  6  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19  9  1  0  0  0  0
 19 10  1  0  0  0  0
 19 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 15  2  0  0  0  0
 21 16  2  0  0  0  0
 22 17  2  0  0  0  0
 23 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0085779

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)C1C(=O)C(=O)C(CC=C(C)C)(CC=C(C)C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O4/c1-11(2)7-9-19(10-8-12(3)4)17(22)14(15(20)13(5)6)16(21)18(19)23/h7-8,13-14H,9-10H2,1-6H3

> <INCHI_KEY>
HMEGPOIWNGKXBR-UHFFFAOYSA-N

> <FORMULA>
C19H26O4

> <MOLECULAR_WEIGHT>
318.4073

> <EXACT_MASS>
318.18310932

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.55828766415125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,3-bis(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)cyclopentane-1,2,4-trione

> <ALOGPS_LOGP>
3.25

> <JCHEM_LOGP>
5.570045930666668

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4177820231032952

> <JCHEM_PKA_STRONGEST_BASIC>
-7.566505598037045

> <JCHEM_POLAR_SURFACE_AREA>
68.28

> <JCHEM_REFRACTIVITY>
91.65929999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,3-bis(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)cyclopentane-1,2,4-trione

> <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      -4.014   3.728   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.031   5.513   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.133   3.728   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.151   5.513   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.052  -2.621   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.773   0.032   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.477   2.904   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.597   2.904   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.029   3.224   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.090   3.224   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.507   4.049   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.627   4.049   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.147  -1.375   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.011  -2.943   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.770   1.651   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5   13                                                            
CONECT    6   13                                                            
CONECT    7    9   11                                                       
CONECT    8   10   12                                                       
CONECT    9    7   19                                                       
CONECT   10    8   19                                                       
CONECT   11    1    2    7                                                  
CONECT   12    3    4    8                                                  
CONECT   13    5    6   15                                                  
CONECT   14   15   16   17                                                  
CONECT   15   13   14   20                                                  
CONECT   16   14   18   21                                                  
CONECT   17   14   19   22                                                  
CONECT   18   16   19   23                                                  
CONECT   19    9   10   17   18                                             
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23   18                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Value	Source
3,3-Bis(3-methyl-2-butenyl)-5-(2-methyl-1-oxopropyl)-1,2,4-cyclopentanetrione, 9ci	HMDB
Cohulupon	HMDB

Chemical Formula

C₁₉H₂₆O₄

Average Mass

318.4073 Da

Monoisotopic Mass

318.18311 Da

IUPAC Name

3,3-bis(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)cyclopentane-1,2,4-trione

Traditional Name

3,3-bis(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)cyclopentane-1,2,4-trione

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)C1C(=O)C(=O)C(CC=C(C)C)(CC=C(C)C)C1=O

InChI Identifier

InChI=1S/C19H26O4/c1-11(2)7-9-19(10-8-12(3)4)17(22)14(15(20)13(5)6)16(21)18(19)23/h7-8,13-14H,9-10H2,1-6H3

InChI Key

HMEGPOIWNGKXBR-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Garcinia subelliptica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta-diketones. These are organic compounds containing two keto groups separated by a single carbon atom.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Beta-diketones

Alternative Parents

Substituents

1,3-diketone
Cyclic ketone
Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic 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	3.25	ALOGPS
logP	5.57	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	1.42	ChemAxon
pKa (Strongest Basic)	-7.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	68.28 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	91.66 m³·mol⁻¹	ChemAxon
Polarizability	35.56 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030064

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001373

KNApSAcK ID

Not Available

Chemspider ID

478981

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

550598

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cohulupone (NP0085779)

MOL for NP0085779 (Cohulupone)

3D MOL for NP0085779 (Cohulupone)

3D SDF for NP0085779 (Cohulupone)

3D-SDF for NP0085779 (Cohulupone)

PDB for NP0085779 (Cohulupone)

3D PDB for NP0085779 (Cohulupone)

SMILES for NP0085779 (Cohulupone)

INCHI for NP0085779 (Cohulupone)

Structure for NP0085779 (Cohulupone)

3D Structure for NP0085779 (Cohulupone)