NP-MRD: Showing NP-Card for Cholesta-4,6-dien-3-one (NP0086966)

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Record Information

Version

2.0

Created at

2022-05-11 16:35:57 UTC

Updated at

2022-05-11 16:35:57 UTC

NP-MRD ID

NP0086966

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cholesta-4,6-dien-3-one

Description

Cholesta-4,6-dien-3-one belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, cholesta-4,6-dien-3-one is considered to be a sterol lipid molecule. Cholesta-4,6-dien-3-one was first documented in 1987 (PMID: 3676336). Cholesta-4,6-dien-3-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 3557306) (PMID: 16757819).

Structure

MOL 3D MOL SDF PDB SMILES InChI

Untitled Document-11
  Mrv0541 02231219312D          

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M  END

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M  END

Untitled Document-11
  Mrv0541 02231219312D          

 31 34  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0086966

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,17-19,22-25H,6-8,11-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
XIWMRKFKSRYSIJ-GYKMGIIDSA-N

> <FORMULA>
C27H42O

> <MOLECULAR_WEIGHT>
382.6218

> <EXACT_MASS>
382.323565966

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
49.21199077135376

> <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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-5-one

> <ALOGPS_LOGP>
6.31

> <JCHEM_LOGP>
7.318213321999998

> <ALOGPS_LOGS>
-7.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.938628620851844

> <JCHEM_PKA_STRONGEST_BASIC>
-4.773828935718656

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
120.68169999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.22e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cholesta-4,6-dien-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-11                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.373  -3.300   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.373  -4.840   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.039  -5.610   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.706  -4.840   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.706  -3.300   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.039  -2.530   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.372  -5.610   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.038  -4.840   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.038  -3.300   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.372  -2.530   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.295  -2.530   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.295  -0.990   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.038  -0.220   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.372  -0.990   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.760  -3.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.665  -1.760   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.760  -0.514   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.236   0.951   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.742   1.271   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.218   2.736   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.725   3.056   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.200   4.521   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.707   4.841   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.111   5.610   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.706  -1.760   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.456   0.542   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       0.051  -4.389   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.038  -1.760   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.694  -4.017   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0       1.147   2.040   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -7.707  -5.610   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   25                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   27                                             
CONECT   10    9    5   14   28                                             
CONECT   11    9   12   15   29                                             
CONECT   12   11   13   17   26                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19   30                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    5                                                            
CONECT   26   12                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   11                                                            
CONECT   30   18                                                            
CONECT   31    2                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
4,6-Cholestadien-3-one	HMDB
4,6-Cholestadiene-3-one	HMDB
Cholest-4,6-dien-3-one	HMDB
Cholesta-4,6-diene-3-one	HMDB

Chemical Formula

C₂₇H₄₂O

Average Mass

382.6218 Da

Monoisotopic Mass

382.32357 Da

IUPAC Name

(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-5-one

Traditional Name

cholesta-4,6-dien-3-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,17-19,22-25H,6-8,11-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

XIWMRKFKSRYSIJ-GYKMGIIDSA-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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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
Oxosteroid
3-oxosteroid
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

Cholesterol and derivatives (LMST01010059 )

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	6.31	ALOGPS
logP	7.32	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	19.94	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.68 m³·mol⁻¹	ChemAxon
Polarizability	49.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0002394

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022993

KNApSAcK ID

Not Available

Chemspider ID

2299095

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6663

PubChem Compound

3034666

PDB ID

Not Available

ChEBI ID

205734

Good Scents ID

Not Available

References

General References

Buchmann MS, Bjorkhem I, Skrede S: Metabolism of the cholestanol precursor cholesta-4,6-dien-3-one in different tissues. Biochim Biophys Acta. 1987 Nov 21;922(2):111-7. doi: 10.1016/0005-2760(87)90144-5. [PubMed:3676336 ]
Bjorkhem I, Skrede S, Buchmann MS, East C, Grundy S: Accumulation of 7 alpha-hydroxy-4-cholesten-3-one and cholesta-4,6-dien-3-one in patients with cerebrotendinous xanthomatosis: effect of treatment with chenodeoxycholic acid. Hepatology. 1987 Mar-Apr;7(2):266-71. doi: 10.1002/hep.1840070210. [PubMed:3557306 ]
Liu ZQ, Shan HY: Cholesterol, not polyunsaturated fatty acids, is target molecule in oxidation induced by reactive oxygen species in membrane of human erythrocytes. Cell Biochem Biophys. 2006;45(2):185-93. doi: 10.1385/CBB:45:2:185. [PubMed:16757819 ]

Showing NP-Card for Cholesta-4,6-dien-3-one (NP0086966)

MOL for NP0086966 (Cholesta-4,6-dien-3-one)

3D MOL for NP0086966 (Cholesta-4,6-dien-3-one)

3D SDF for NP0086966 (Cholesta-4,6-dien-3-one)

3D-SDF for NP0086966 (Cholesta-4,6-dien-3-one)

PDB for NP0086966 (Cholesta-4,6-dien-3-one)

3D PDB for NP0086966 (Cholesta-4,6-dien-3-one)

SMILES for NP0086966 (Cholesta-4,6-dien-3-one)

INCHI for NP0086966 (Cholesta-4,6-dien-3-one)

Structure for NP0086966 (Cholesta-4,6-dien-3-one)

3D Structure for NP0086966 (Cholesta-4,6-dien-3-one)