NP-MRD: Showing NP-Card for cholest-4-ene-3,6-dione (NP0311885)

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Record Information

Version

2.0

Created at

2022-09-11 08:11:36 UTC

Updated at

2022-09-11 08:11:37 UTC

NP-MRD ID

NP0311885

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cholest-4-ene-3,6-dione

Description

Cholest-4-ene-3,6-dione belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. cholest-4-ene-3,6-dione is found in Cystoseira myrica and Dendrophyllia cornigera. cholest-4-ene-3,6-dione was first documented in 2009 (PMID: 19576917). Based on a literature review a small amount of articles have been published on Cholest-4-ene-3,6-dione (PMID: 23326358) (PMID: 32209376) (PMID: 23121678) (PMID: 22634836).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112210112D          

 29 32  0  0  1  0            999 V2000
    6.9960   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7104   -2.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7104   -3.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4249   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1394   -2.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8538   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5683   -2.5011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5683   -3.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2828   -2.0886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.3690   -1.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1760   -1.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5885   -1.8111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.3955   -1.9826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9475   -1.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7545   -1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3065   -0.9280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0094   -2.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8164   -2.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0713   -3.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8783   -3.4534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5193   -3.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7123   -3.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4574   -2.9388    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9053   -3.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6504   -2.7673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0984   -3.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2914   -3.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0365   -2.4242    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4234   -2.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  2  4  1  0  0  0  0
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  5  6  1  0  0  0  0
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  9  7  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
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 27 28  1  0  0  0  0
 12 28  1  0  0  0  0
  9 28  1  0  0  0  0
 28 29  1  1  0  0  0
M  END

     RDKit          3D

 71 74  0  0  0  0  0  0  0  0999 V2000
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   -2.0852   -1.2402    0.8575 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309112210112D          

 29 32  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0311885

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC(=O)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-16-25(29)24-15-19(28)11-13-27(24,5)23(20)12-14-26(21,22)4/h15,17-18,20-23H,6-14,16H2,1-5H3/t18-,20+,21-,22+,23+,26-,27-/m1/s1

> <INCHI_KEY>
GWOSBUGZGFVDDS-LKGWFGLDSA-N

> <FORMULA>
C27H42O2

> <MOLECULAR_WEIGHT>
398.631

> <EXACT_MASS>
398.318480592

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
49.82067736842735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,8-dione

> <JCHEM_LOGP>
7.012851617333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.65496623725179

> <JCHEM_PKA_STRONGEST_BASIC>
-6.6101311085305365

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
120.25829999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,8-dione

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      13.059  -3.899   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.393  -4.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.393  -6.209   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.726  -3.899   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.060  -4.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.394  -3.899   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.728  -4.669   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.728  -6.209   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.061  -3.899   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.222  -2.367   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.729  -2.047   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.499  -3.381   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.005  -3.701   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.035  -2.556   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.542  -2.877   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      28.572  -1.732   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      28.018  -4.341   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.524  -4.661   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.000  -6.126   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      31.506  -6.446   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      28.969  -7.271   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.463  -6.950   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.987  -5.486   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.957  -6.630   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      25.481  -5.166   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.450  -6.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.944  -5.990   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      22.468  -4.525   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.324  -5.556   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   28                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   28                                                  
CONECT   13   12   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   13   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   12    9   29                                             
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
Cholest-4-en-3,6-dione	MeSH

Chemical Formula

C₂₇H₄₂O₂

Average Mass

398.6310 Da

Monoisotopic Mass

398.31848 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC(=O)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C27H42O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-16-25(29)24-15-19(28)11-13-27(24,5)23(20)12-14-26(21,22)4/h15,17-18,20-23H,6-14,16H2,1-5H3/t18-,20+,21-,22+,23+,26-,27-/m1/s1

InChI Key

GWOSBUGZGFVDDS-LKGWFGLDSA-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
Cystoseira myrica	LOTUS Database	35616633
Dendrophyllia cornigera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
6-oxosteroid
Oxosteroid
3-oxosteroid
3-oxo-delta-4-steroid
Delta-4-steroid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	7.01	ChemAxon
pKa (Strongest Acidic)	19.65	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Rotatable Bond Count	5	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

92093

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101934

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tayade AB, Dhar P, Kumar J, Sharma M, Chauhan RS, Chaurasia OP, Srivastava RB: Chemometric profile of root extracts of Rhodiola imbricata Edgew. with hyphenated gas chromatography mass spectrometric technique. PLoS One. 2013;8(1):e52797. doi: 10.1371/journal.pone.0052797. Epub 2013 Jan 10. [PubMed:23326358 ]
Sali VK, Mani S, Meenaloshani G, Velmurugan Ilavarasi A, Vasanthi HR: Type 5 17-hydroxysteroid dehydrogenase/prostaglandin F synthase (AKR1C3) inhibition and potential anti-proliferative activity of cholest-4-ene-3,6-dione in MCF-7 breast cancer cells. Steroids. 2020 Jul;159:108638. doi: 10.1016/j.steroids.2020.108638. Epub 2020 Mar 21. [PubMed:32209376 ]
Geng X, Mague JT, Pascal RA: Synthesis and chiroptical properties of arylimines of cholest-4-ene-3,6-dione. J Org Chem. 2012 Dec 7;77(23):10920-4. doi: 10.1021/jo301591g. Epub 2012 Nov 12. [PubMed:23121678 ]
Chompoo J, Upadhyay A, Gima S, Fukuta M, Tawata S: Antiatherogenic properties of acetone extract of Alpinia zerumbet seeds. Molecules. 2012 May 25;17(6):6237-48. doi: 10.3390/molecules17066237. [PubMed:22634836 ]
Hamdy AH, Aboutabl EA, Sameer S, Hussein AA, Diaz-Marrero AR, Darias J, Cueto M: 3-Keto-22-epi-28-nor-cathasterone, a brassinosteroid-related metabolite from Cystoseira myrica. Steroids. 2009 Nov;74(12):927-30. doi: 10.1016/j.steroids.2009.06.008. Epub 2009 Jul 2. [PubMed:19576917 ]
LOTUS database [Link]

Showing NP-Card for cholest-4-ene-3,6-dione (NP0311885)

MOL for NP0311885 (cholest-4-ene-3,6-dione)

3D MOL for NP0311885 (cholest-4-ene-3,6-dione)

3D SDF for NP0311885 (cholest-4-ene-3,6-dione)

3D-SDF for NP0311885 (cholest-4-ene-3,6-dione)

PDB for NP0311885 (cholest-4-ene-3,6-dione)

3D PDB for NP0311885 (cholest-4-ene-3,6-dione)

SMILES for NP0311885 (cholest-4-ene-3,6-dione)

INCHI for NP0311885 (cholest-4-ene-3,6-dione)

Structure for NP0311885 (cholest-4-ene-3,6-dione)

3D Structure for NP0311885 (cholest-4-ene-3,6-dione)