NP-MRD: Showing NP-Card for 5,9-Epidioxy-3-hydroxyergost-7-en-6-one (NP0047428)

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Record Information

Version

2.0

Created at

2022-03-17 20:40:02 UTC

Updated at

2022-03-17 20:40:02 UTC

NP-MRD ID

NP0047428

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,9-Epidioxy-3-hydroxyergost-7-en-6-one

Description

5,9-Epidioxy-3-hydroxyergost-7-en-6-one belongs to the class of organic compounds known as ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position. 5,9-Epidioxy-3-hydroxyergost-7-en-6-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5,9-epidioxy-3-hydroxyergost-7-en-6-one has been detected, but not quantified in, mushrooms. This could make 5,9-epidioxy-3-hydroxyergost-7-en-6-one a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241207582D          

 32 36  0  0  0  0            999 V2000
   -3.7067   -0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7067   -1.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9924   -1.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -1.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9924    0.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653   -1.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525   -1.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525   -0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    0.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1410    0.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1410    0.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525    1.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    0.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6391   -0.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1195    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6391    1.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4223   -1.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -2.0607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653   -0.8236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1410    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8951    1.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432    2.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029    2.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2548    1.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0626    1.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6144    0.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3185    2.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3584    0.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4223    1.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653   -2.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 20  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 19  1  0  0  0  0
  7  8  1  0  0  0  0
  7 32  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 10 21  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 22  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 23  1  0  0  0  0
 20 21  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  END


  Mrv0541 02241207582D          

 32 36  0  0  0  0            999 V2000
   -3.7067   -0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7067   -1.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9924   -1.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -1.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9924    0.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653   -1.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525   -1.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525   -0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    0.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1410    0.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1410    0.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525    1.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    0.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6391   -0.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1195    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6391    1.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4223   -1.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -2.0607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653   -0.8236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1410    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8951    1.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432    2.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029    2.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2548    1.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0626    1.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6144    0.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3185    2.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3584    0.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4223    1.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653   -2.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 20  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 19  1  0  0  0  0
  7  8  1  0  0  0  0
  7 32  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 10 21  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 22  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 23  1  0  0  0  0
 20 21  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047428

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(C)CCC(C)C1CCC2C3=CC(=O)C45CC(O)CCC4(C)C3(CCC12C)OO5

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O4/c1-17(2)18(3)7-8-19(4)21-9-10-22-23-15-24(30)28-16-20(29)11-12-26(28,6)27(23,31-32-28)14-13-25(21,22)5/h15,17-22,29H,7-14,16H2,1-6H3

> <INCHI_KEY>
FZOPHVRKJMCTDV-UHFFFAOYSA-N

> <FORMULA>
C28H44O4

> <MOLECULAR_WEIGHT>
444.6466

> <EXACT_MASS>
444.323959896

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
53.084681533925824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-(5,6-dimethylheptan-2-yl)-16-hydroxy-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-3-en-2-one

> <ALOGPS_LOGP>
5.84

> <JCHEM_LOGP>
6.358664464666665

> <ALOGPS_LOGS>
-6.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.692149151173975

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.141281551841924

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7369499112751123

> <JCHEM_POLAR_SURFACE_AREA>
55.76

> <JCHEM_REFRACTIVITY>
126.11079999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.08e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(5,6-dimethylheptan-2-yl)-16-hydroxy-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.919  -0.764   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.919  -2.306   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.586  -3.076   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.255  -2.306   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.255  -0.764   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.586   0.004   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.922  -3.076   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.591  -2.306   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.591  -0.764   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.922   0.004   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.263   0.004   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.263   1.537   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.591   2.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.922   1.537   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.193  -0.469   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.090   0.772   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.193   2.007   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -8.255  -3.076   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.255   0.772   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.255  -3.847   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.922  -1.537   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.263   3.079   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.671   3.472   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.641   4.617   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.179   3.790   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.209   2.645   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.717   2.963   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.747   1.817   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.195   4.427   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.269   0.353   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.255   2.136   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.922  -4.617   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   20                                             
CONECT    5    4    6   10   19                                             
CONECT    6    1    5                                                       
CONECT    7    4    8   32                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14   21                                             
CONECT   11    9   12   15                                                  
CONECT   12   11   13   17   22                                             
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16   23                                                  
CONECT   18    2                                                            
CONECT   19    5                                                            
CONECT   20    4   21                                                       
CONECT   21   10   20                                                       
CONECT   22   12                                                            
CONECT   23   17   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27   30   31                                                  
CONECT   29   27                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32    7                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
5,9-Epidioxy-3-hydroxy-24-methylcholest-7-en-6-one	HMDB

Chemical Formula

C₂₈H₄₄O₄

Average Mass

444.6466 Da

Monoisotopic Mass

444.32396 Da

IUPAC Name

8-(5,6-dimethylheptan-2-yl)-16-hydroxy-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-3-en-2-one

Traditional Name

8-(5,6-dimethylheptan-2-yl)-16-hydroxy-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-3-en-2-one

CAS Registry Number

211486-17-8

SMILES

CC(C)C(C)CCC(C)C1CCC2C3=CC(=O)C45CC(O)CCC4(C)C3(CCC12C)OO5

InChI Identifier

InChI=1S/C28H44O4/c1-17(2)18(3)7-8-19(4)21-9-10-22-23-15-24(30)28-16-20(29)11-12-26(28,6)27(23,31-32-28)14-13-25(21,22)5/h15,17-22,29H,7-14,16H2,1-6H3

InChI Key

FZOPHVRKJMCTDV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergostane steroids

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic 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	5.84	ALOGPS
logP	6.36	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	15.14	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.11 m³·mol⁻¹	ChemAxon
Polarizability	53.08 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0032667

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010620

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85218115

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 5,9-Epidioxy-3-hydroxyergost-7-en-6-one (NP0047428)

MOL for NP0047428 (5,9-Epidioxy-3-hydroxyergost-7-en-6-one)

3D MOL for NP0047428 (5,9-Epidioxy-3-hydroxyergost-7-en-6-one)

3D SDF for NP0047428 (5,9-Epidioxy-3-hydroxyergost-7-en-6-one)

3D-SDF for NP0047428 (5,9-Epidioxy-3-hydroxyergost-7-en-6-one)

PDB for NP0047428 (5,9-Epidioxy-3-hydroxyergost-7-en-6-one)

3D PDB for NP0047428 (5,9-Epidioxy-3-hydroxyergost-7-en-6-one)

SMILES for NP0047428 (5,9-Epidioxy-3-hydroxyergost-7-en-6-one)

INCHI for NP0047428 (5,9-Epidioxy-3-hydroxyergost-7-en-6-one)

Structure for NP0047428 (5,9-Epidioxy-3-hydroxyergost-7-en-6-one)

3D Structure for NP0047428 (5,9-Epidioxy-3-hydroxyergost-7-en-6-one)