MiMeDB: Showing metabocard for Cholest-5-en-3-one (MMDBc0057116)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-10-17 17:54:06 UTC

Update Date

2022-10-17 17:54:06 UTC

Metabolite ID

MMDBc0057116

Metabolite Identification

Common Name

Cholest-5-en-3-one

Description

5-Cholesten-3-one, also known as cholesterone or oxidized cholesterol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 5-cholesten-3-one is considered to be a sterol. Based on a literature review very few articles have been published on 5-Cholesten-3-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652310172219542D          

 32 35  0  0  1  0            999 V2000
    4.2348   -2.0294    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780   -1.2055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5243   -1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9722   -0.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3847   -0.2135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9368    0.3996    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1298    0.5711    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5778   -0.0420    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3228    0.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0679    1.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6199    2.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3650    2.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9170    3.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6621    4.3227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240    3.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9789    2.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4269    1.9688    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2339    1.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6818    1.1842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8749    1.3557    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4888    1.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7437    0.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -0.3850    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9763   -0.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -1.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9924   -2.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7069   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4214   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1358   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8503   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5648   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8503   -2.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
  2 25  1  1  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  END


  Mrv1652310172219542D          

 32 35  0  0  1  0            999 V2000
    4.2348   -2.0294    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780   -1.2055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5243   -1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9722   -0.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3847   -0.2135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9368    0.3996    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1298    0.5711    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5778   -0.0420    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3228    0.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0679    1.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6199    2.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3650    2.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9170    3.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6621    4.3227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240    3.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9789    2.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4269    1.9688    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2339    1.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6818    1.1842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8749    1.3557    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4888    1.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7437    0.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -0.3850    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9763   -0.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -1.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9924   -2.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7069   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4214   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1358   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8503   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5648   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8503   -2.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
  2 25  1  1  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0057116

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O/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/h9,18-19,22-25H,6-8,10-17H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
GGCLNOIGPMGLDB-GYKMGIIDSA-N

> <FORMULA>
C27H44O

> <MOLECULAR_WEIGHT>
384.648

> <EXACT_MASS>
384.339216037

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
49.75715748024587

> <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-7-en-5-one

> <ALOGPS_LOGP>
6.85

> <JCHEM_LOGP>
7.320389832333332

> <ALOGPS_LOGS>
-7.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.227856548613076

> <JCHEM_PKA_STRONGEST_BASIC>
-7.429976128468029

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
119.58839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.64e-05 g/l

> <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-7-en-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 17-OCT-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-OCT-22         0                                  
HETATM    1  H   UNK     0       7.905  -3.788   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       7.986  -2.250   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.579  -2.877   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.548  -1.732   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.318  -0.399   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       7.349   0.746   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       5.842   1.066   0.000  0.00  0.00           C+0
HETATM    8  H   UNK     0       4.812  -0.078   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0       4.336   1.386   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.860   2.851   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.891   3.995   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.415   5.460   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.445   6.604   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.969   8.069   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.951   6.284   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.427   4.820   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.397   3.675   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.903   3.355   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.873   2.211   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       5.366   2.531   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       8.379   1.890   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.855   0.426   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.825  -0.719   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.289  -1.195   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.319  -3.020   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.319  -4.560   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.653  -2.250   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.987  -3.020   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.320  -2.250   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.654  -3.020   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.988  -2.250   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.654  -4.560   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23   25                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   23                                             
CONECT    6    5                                                            
CONECT    7    5    8    9   19                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   11   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    7   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    2    5   24                                             
CONECT   24   23                                                            
CONECT   25    2   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

Synonyms

Value	Source
Cholestenone	ChEBI
Cholesterone	ChEBI
Delta(5)-Cholestenone	ChEBI
Oxidized cholesterol	ChEBI
Δ(5)-cholestenone	Generator
Cholest-5-en-3-one	MeSH

Molecular Formula

C₂₇H₄₄O

Average Mass

384.648

Monoisotopic Mass

384.339216037

IUPAC Name

(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-7-en-5-one

Traditional Name

(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-7-en-5-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C27H44O/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/h9,18-19,22-25H,6-8,10-17H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

GGCLNOIGPMGLDB-GYKMGIIDSA-N

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
3-oxo-delta-5-steroid
Delta-5-steroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cholestanoid (CHEBI:63906 )
3-oxo Delta(5)-steroid (CHEBI:63906 )
Cholesterol and derivatives (LMST01010248 )

Functional Ontology

Not Available

Physical Properties

State

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.6e-05 g/L	ALOGPS
logP	6.85	ALOGPS
logP	7.32	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	16.23	ChemAxon
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	119.59 m³·mol⁻¹	ChemAxon
Polarizability	49.76 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

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00062390

Chemspider ID

8083759

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9908107

PDB ID

Not Available

ChEBI ID

63906

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Cholest-5-en-3-one (MMDBc0057116)

MOL for #<Metabolite:0x00007fed1423b280>

3D MOL for #<Metabolite:0x00007fed1423b280>

3D SDF for #<Metabolite:0x00007fed1423b280>

3D-SDF for #<Metabolite:0x00007fed1423b280>

PDB for #<Metabolite:0x00007fed1423b280>

3D PDB for #<Metabolite:0x00007fed1423b280>

SMILES for #<Metabolite:0x00007fed1423b280>

INCHI for #<Metabolite:0x00007fed1423b280>

Structure for #<Metabolite:0x00007fed1423b280>

3D Structure for #<Metabolite:0x00007fed1423b280>