MiMeDB: Showing metabocard for Episterol (MMDBc0008962)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 01:37:35 UTC

Update Date

2022-12-15 22:51:44 UTC

Metabolite ID

MMDBc0008962

Metabolite Identification

Common Name

Episterol

Description

(1R,2S,5S,7R,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol 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. Based on a literature review very few articles have been published on (1R,2S,5S,7R,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol.

Structure

MOL SDF PDB SMILES InChI

Episterol
  Mrv1652309242002242D          

 29 32  0  0  0  0            999 V2000
    2.8611   -4.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896   -3.8975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3027   -3.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0873   -3.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7004   -3.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4850   -3.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5289   -2.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1420   -1.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7443   -1.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9049   -3.6425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2375   -4.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5701   -3.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.8579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6500   -2.8579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4290    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4705   -2.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  1  0  0  0
 22 28  1  1  0  0  0
 14 29  1  1  0  0  0
 14 10  1  0  0  0  0
 18 13  1  0  0  0  0
 22 17  1  0  0  0  0
 26 21  1  0  0  0  0
M  END

Episterol
  Mrv1652309242002242D          

 29 32  0  0  0  0            999 V2000
    2.8611   -4.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896   -3.8975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3027   -3.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0873   -3.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7004   -3.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4850   -3.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5289   -2.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1420   -1.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7443   -1.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9049   -3.6425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2375   -4.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5701   -3.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.8579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6500   -2.8579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4290    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4705   -2.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  1  0  0  0
 22 28  1  1  0  0  0
 14 29  1  1  0  0  0
 14 10  1  0  0  0  0
 18 13  1  0  0  0  0
 22 17  1  0  0  0  0
 26 21  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0008962

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O/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/h10,18,20-22,24-26,29H,3,7-9,11-17H2,1-2,4-6H3/t20-,21-,22+,24-,25+,26+,27+,28-/m1/s1

> <INCHI_KEY>
BTCAEOLDEYPGGE-XLOMHNBOSA-N

> <FORMULA>
C28H46O

> <MOLECULAR_WEIGHT>
398.675

> <EXACT_MASS>
398.354866101

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.4589917081864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5S,7R,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

> <ALOGPS_LOGP>
7.16

> <JCHEM_LOGP>
7.052262316

> <ALOGPS_LOGS>
-6.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.361777845540015

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3283583703607977

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
124.94259999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.24e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,7R,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Episterol                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-SEP-20         0                                  
HETATM    1  C   UNK     0       5.341  -8.782   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.021  -7.275   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.165  -6.245   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.630  -6.721   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.774  -5.690   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.239  -6.166   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.454  -4.184   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.598  -3.153   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.989  -3.708   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.556  -6.799   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.310  -7.705   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.064  -6.799   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.540  -5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -5.335   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.850  -4.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080  -2.667   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.770  -4.001   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.770  -4.001   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.540  -2.667   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.540   2.667   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.612  -5.496   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    2   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   29   10                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   13                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   28   17                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25                                                            
CONECT   28   22                                                            
CONECT   29   14                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

Synonyms

Not Available

Molecular Formula

C₂₈H₄₆O

Average Mass

398.675

Monoisotopic Mass

398.354866101

IUPAC Name

(1R,2S,5S,7R,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

Traditional Name

(1R,2S,5S,7R,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

CAS Registry Number

Not Available

SMILES

CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C28H46O/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/h10,18,20-22,24-26,29H,3,7-9,11-17H2,1-2,4-6H3/t20-,21-,22+,24-,25+,26+,27+,28-/m1/s1

InChI Key

BTCAEOLDEYPGGE-XLOMHNBOSA-N

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-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Delta-7-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00022 g/L	ALOGPS
logP	7.16	ALOGPS
logP	7.05	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	18.36	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	124.94 m³·mol⁻¹	ChemAxon
Polarizability	51.46 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

Extracellular
Membrane

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
Eukaryota/Fungi	Ascomycota	7	Human feces; Human saliva	Metabolic reconstruction; Unknown

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

Not Available

Chemspider ID

78442030

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585457

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
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 Episterol (MMDBc0008962)

MOL for #<Metabolite:0x00007fecddc17d80>

3D MOL for #<Metabolite:0x00007fecddc17d80>

3D SDF for #<Metabolite:0x00007fecddc17d80>

3D-SDF for #<Metabolite:0x00007fecddc17d80>

PDB for #<Metabolite:0x00007fecddc17d80>

3D PDB for #<Metabolite:0x00007fecddc17d80>

SMILES for #<Metabolite:0x00007fecddc17d80>

INCHI for #<Metabolite:0x00007fecddc17d80>

Structure for #<Metabolite:0x00007fecddc17d80>

3D Structure for #<Metabolite:0x00007fecddc17d80>