NP-MRD: Showing NP-Card for 5alpha-Campestan-3-one (NP0044315)

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Record Information

Version

2.0

Created at

2022-02-14 20:48:31 UTC

Updated at

2022-03-10 22:17:42 UTC

NP-MRD ID

NP0044315

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5alpha-Campestan-3-one

Description

5Alpha-campestan-3-one, also known as 3-dehydro-campestanol or methylcholestanone, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, 5alpha-campestan-3-one is considered to be a sterol lipid molecule. 5Alpha-campestan-3-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5Alpha-Campestan-3-one is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042000342D          

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M  END

     RDKit          3D

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M  END


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 14 15  1  6  0  0  0
 16 17  1  1  0  0  0
 18 21  1  6  0  0  0
 19 20  1  1  0  0  0
 22 23  1  0  0  0  0
 22 29  1  0  0  0  0
 23 28  1  0  0  0  0
 28 31  1  0  0  0  0
 24 29  1  0  0  0  0
 26 24  1  0  0  0  0
 24 25  1  0  0  0  0
 28 27  1  6  0  0  0
 29 30  1  1  0  0  0
 31 32  1  6  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0044315

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h18-21,23-26H,7-17H2,1-6H3/t19-,20-,21+,23+,24-,25+,26+,27+,28-/m1/s1

> <INCHI_KEY>
DDJMOMHMVFXEQF-JBQSTXLYSA-N

> <FORMULA>
C28H48O

> <MOLECULAR_WEIGHT>
400.691

> <EXACT_MASS>
400.370516166

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
52.02003789689965

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,7S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one

> <ALOGPS_LOGP>
6.41

> <JCHEM_LOGP>
8.01298841

> <ALOGPS_LOGS>
-7.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.352808751885236

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
123.28699999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.22e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,7S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -3.179   0.404   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.512  -0.366   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.179  -2.676   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.845  -1.906   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.511  -2.676   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.822  -1.906   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.845  -0.366   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.511   1.944   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.822   2.714   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.621  -0.071   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.526   1.174   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.845   1.174   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      -1.845  -3.446   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0      -0.511   0.404   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0      -0.511  -1.136   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       0.822  -0.366   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       0.822   1.174   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0       2.156   0.404   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.156   1.944   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.156   3.484   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       2.156  -1.136   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0       6.288   3.960   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.954   4.730   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.956   3.960   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.956   2.420   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.289   4.730   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.287   4.730   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.621   3.960   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.622   4.730   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.622   6.270   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.621   2.420   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0       4.954   3.190   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0      -4.512  -1.906   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.846  -2.676   0.000  0.00  0.00           O+0
CONECT    1    7    2                                                       
CONECT    2    1   33                                                       
CONECT    3    4   33                                                       
CONECT    4    7    3    5   13                                             
CONECT    5    6    4                                                       
CONECT    6   16    5                                                       
CONECT    7   14    4   12    1                                             
CONECT    8   14    9                                                       
CONECT    9   19    8                                                       
CONECT   10   18   11                                                       
CONECT   11   31   10                                                       
CONECT   12    7                                                            
CONECT   13    4                                                            
CONECT   14    8    7   16   15                                             
CONECT   15   14                                                            
CONECT   16   18   14    6   17                                             
CONECT   17   16                                                            
CONECT   18   19   16   10   21                                             
CONECT   19   18   31    9   20                                             
CONECT   20   19                                                            
CONECT   21   18                                                            
CONECT   22   23   29                                                       
CONECT   23   22   28                                                       
CONECT   24   29   26   25                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   28                                                            
CONECT   28   23   31   27                                                  
CONECT   29   22   24   30                                                  
CONECT   30   29                                                            
CONECT   31   19   11   28   32                                             
CONECT   32   31                                                            
CONECT   33    3    2   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
(24R)-24-Methyl-5alpha-cholestan-3-one	ChEBI
(24R)-5alpha-Ergostan-3-one	ChEBI
3-Dehydro-campestanol	ChEBI
Campestan-3-one	ChEBI
Methylcholestanone	ChEBI
(24R)-24-Methyl-5a-cholestan-3-one	Generator
(24R)-24-Methyl-5α-cholestan-3-one	Generator
(24R)-5a-Ergostan-3-one	Generator
(24R)-5Α-ergostan-3-one	Generator
5a-Campestan-3-one	Generator
5Α-campestan-3-one	Generator
(5alpha)-Campestan-3-one	HMDB
(5alpha,24R)-Ergostan-3-one	HMDB
(5α)-Campestan-3-one	HMDB
(5α,24R)-Ergostan-3-one	HMDB
5alpha-Campestan-3-one	HMDB
Ostreastanone	HMDB

Chemical Formula

C₂₈H₄₈O

Average Mass

400.6910 Da

Monoisotopic Mass

400.37052 Da

IUPAC Name

(1S,2S,7S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one

Traditional Name

(1S,2S,7S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one

CAS Registry Number

27212-88-0

SMILES

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

InChI Identifier

InChI=1S/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h18-21,23-26H,7-17H2,1-6H3/t19-,20-,21+,23+,24-,25+,26+,27+,28-/m1/s1

InChI Key

DDJMOMHMVFXEQF-JBQSTXLYSA-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
Arabidopsis thaliana	Plant	KNApSAcK
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
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 ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergosterols and derivatives

Alternative Parents

Substituents

Ergosterol-skeleton
3-oxo-5-alpha-steroid
Oxosteroid
3-oxosteroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:18533 )
brassinosteroid (CHEBI:18533 )
Ergosterols and C24-methyl derivatives (LMST01030123 )

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	6.41	ALOGPS
logP	8.01	ChemAxon
logS	-7.5	ALOGPS
pKa (Strongest Basic)	-7.4	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	123.29 m³·mol⁻¹	ChemAxon
Polarizability	52.02 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

HMDB0012116

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028780

KNApSAcK ID

Not Available

Chemspider ID

17221007

KEGG Compound ID

C15786

BioCyc ID

CPD-709

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16061343

PDB ID

Not Available

ChEBI ID

18533

Good Scents ID

Not Available

References

General References

Kyselka J, Honzikova T, Vachalova T, Jiraskova T, Alishevich K, Rottnerova Z, Brychova V, Bercikova M, Hradkova I, Filip V: Formation of 5alpha-Sitostan-3-one, 5alpha-Campestan-3-one, and Steroidal Hydrocarbons in Edible Oils during Catalytic Hydrogenation. J Agric Food Chem. 2019 Sep 4;67(35):9916-9925. doi: 10.1021/acs.jafc.9b03054. Epub 2019 Aug 22. [PubMed:31398025 ]
Nomura T, Jager CE, Kitasaka Y, Takeuchi K, Fukami M, Yoneyama K, Matsushita Y, Nyunoya H, Takatsuto S, Fujioka S, Smith JJ, Kerckhoffs LH, Reid JB, Yokota T: Brassinosteroid deficiency due to truncated steroid 5alpha-reductase causes dwarfism in the lk mutant of pea. Plant Physiol. 2004 Aug;135(4):2220-9. doi: 10.1104/pp.104.043786. Epub 2004 Jul 30. [PubMed:15286289 ]

Showing NP-Card for 5alpha-Campestan-3-one (NP0044315)

MOL for NP0044315 (5alpha-Campestan-3-one)

3D MOL for NP0044315 (5alpha-Campestan-3-one)

3D SDF for NP0044315 (5alpha-Campestan-3-one)

3D-SDF for NP0044315 (5alpha-Campestan-3-one)

PDB for NP0044315 (5alpha-Campestan-3-one)

3D PDB for NP0044315 (5alpha-Campestan-3-one)

SMILES for NP0044315 (5alpha-Campestan-3-one)

INCHI for NP0044315 (5alpha-Campestan-3-one)

Structure for NP0044315 (5alpha-Campestan-3-one)

3D Structure for NP0044315 (5alpha-Campestan-3-one)