NP-MRD: Showing NP-Card for Ergosterol peroxide (NP0048945)

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Record Information

Version

2.0

Created at

2022-03-17 21:04:40 UTC

Updated at

2022-03-17 21:04:40 UTC

NP-MRD ID

NP0048945

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ergosterol peroxide

Description

Ergosterol peroxide, also known as 5a,8a-peroxyergosterol, 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. Ergosterol peroxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, ergosterol peroxide has been detected, but not quantified in, fruits and pineapples. This could make ergosterol peroxide a potential biomarker for the consumption of these foods. Ergosterol peroxide is found in Andrographis paniculata, Aspergillus fumigatus, Aspergillus ochraceus, Benincasa hispida, Bombyx mori, Breynia fruticosa, Catathelasma ventricosa, Catathelasma ventricosum, Cetraria islandica, Cetraria richardsonii, Chaetomium cochliodes, Chaetomium elatum, Chlorella vulgaris, Cladosporium sp., Cordyceps tenuipes, Daedalea quercina, Daedaleopsis confragosa var.tricolor, Daedaleopsis quercina, Degelia gayana, Diaporthe convolvuli, Duranta erecta, Duranta repens, Emericellopsis minima, Etlingera elatior , Ficus nervosa, Fomes fomentarius, Fomitopsis fomentarius, Ganoderma applanatum , Ganoderma australe, Ganoderma carnosum, Ganoderma lucidum , Ganoderma pfeifferi, Ganoderma sinense, Ganoderma tsugae, Grifola frondosa, Gynura japonica, Haloxylon salicornicum, Hericium erinaceus, Huperzia serrata, Hypholoma fasciculare, Hypholoma lateritium, Inonotus obliquus, Inula anatolica, Junceella fragilis, Lactarius hatsudake, Lactarius uvidus, Lactarius volemus, Laetiporus sulphureus , Lethariella cladonioides, Leucaena leucocephala, Leucoagaricus americanus, Lichtheimia corymbifera, Melia azedarach, Melilotus messanensis, Microporus affinis, Morchella esculenta, Nigrospora oryzae, Ochrolechia parella, Ophiocordyceps sinensis, Ovatospora brasiliensis, Panellus eryngii (DC.:FR.) QUEL., Pellia epiphylla, Penicillium chrysogenum, Penicillium commune, Penicillium oxalicum, Phaeolepiota aurea, Fuscoporia torulosa, Pisolithus arhizus, Pisolithus tinctorius , Pisonia aculeata, Pleurotus eryngii, Podostictina encoensis, Polyporus tuberaster, Polyporus umbellatus, Porodaedalea pini, Psilocybe argentipes, Pulicaria canariensis, Ramalina hierrensis, Ramaria botrytis, Ramaria botrytis (Pers.) Ricken , Rhizoplaca melanophthalma, Rhizopus oryzae, Rhynchosia minima, Russula subnigricans, Sarcodon aspratus, Sarcodon scabrosus, Saussurea hieracioides, Scleroderma polyrhizum, Scolochloa festucacea, Sinacalia tangutica, Sinularia flexibilis, Spiranthes sinensis, Chaetomium longicolleum, Stereocaulon azoreum, Stereum hirsutum, Sticta weigelii, Taiwanofungus camphoratus, Teucrium heterophyllum, Thamnolia subuliformis, Thamnolia subuniformis, Cortinarius vibratilis, Mallotus nudiflorus, Tricholoma matsutake, Tuber indicum, Typha latifolia, Usnea articulata, Verbena officinalis, Xanthium strumarium and Zantedeschia aethiopica. Ergosterol peroxide was first documented in 2007 (PMID: 17357175). Ergosterol peroxide (5α,8α-epidioxy-22E-ergosta-6,22-dien-3β-ol) is a steroid derivative (PMID: 19475991).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241214502D          

 31 35  0  0  0  0            999 V2000
   -3.7070   -0.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7070   -1.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9928   -2.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2799   -1.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2799   -0.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9928   -0.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5656   -2.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525   -1.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525   -0.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5656   -0.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1412   -0.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1412    0.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525    0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5656    0.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392   -0.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1195    0.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392    0.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4227   -2.0610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2799    0.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8670   -0.9324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2834   -1.5160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1412    1.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8952    1.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432    2.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7030    1.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2550    1.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0629    1.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6149    0.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3189    1.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3589   -0.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4227    0.7315    0.0000 C   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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 21  1  0  0  0  0
 10 14  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  2  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 02241214502D          

 31 35  0  0  0  0            999 V2000
   -3.7070   -0.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7070   -1.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9928   -2.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2799   -1.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2799   -0.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9928   -0.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5656   -2.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525   -1.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525   -0.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5656   -0.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1412   -0.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1412    0.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525    0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5656    0.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392   -0.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1195    0.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392    0.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4227   -2.0610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2799    0.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8670   -0.9324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2834   -1.5160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1412    1.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8952    1.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432    2.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7030    1.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2550    1.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0629    1.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6149    0.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3189    1.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3589   -0.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4227    0.7315    0.0000 C   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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 21  1  0  0  0  0
 10 14  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  2  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>
NP0048945

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(C)\C=C\C(C)C1CCC2C1(C)CCC1C3(C)CCC(O)CC33OOC21C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,15-16,18-24,29H,9-14,17H2,1-6H3/b8-7+

> <INCHI_KEY>
VXOZCESVZIRHCJ-BQYQJAHWSA-N

> <FORMULA>
C28H44O3

> <MOLECULAR_WEIGHT>
428.6472

> <EXACT_MASS>
428.329045274

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
51.74645865646431

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(3E)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol

> <ALOGPS_LOGP>
6.27

> <JCHEM_LOGP>
6.347938847666668

> <ALOGPS_LOGS>
-7.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.1490254826832

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7336162538743682

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
126.82409999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.01e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(3E)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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      -6.920  -1.535   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.920  -3.076   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.587  -3.847   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.256  -3.076   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.256  -1.535   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.587  -0.767   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.922  -3.847   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.591  -3.076   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.591  -1.535   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.922  -0.767   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.264  -0.767   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.264   0.767   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.591   1.532   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.922   0.767   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.193  -1.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.090   0.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.193   1.237   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -8.256  -3.847   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.256   0.006   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.485  -1.740   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.396  -2.830   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.264   2.309   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.671   2.701   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.641   3.847   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.179   3.020   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.209   1.874   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.717   2.193   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.748   1.047   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.195   3.657   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.270  -0.417   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.256   1.365   0.000  0.00  0.00           C+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                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   21                                             
CONECT   10    5    9   14                                                  
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    9   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                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
(-)-5alpha,8alpha-Epidioxyergosta-6,22-dien-3beta-ol	HMDB
5a,8a-Peroxyergosterol	HMDB
5alpha,8alpha-Epidioxyergosta-6,22-dien-3beta-ol	HMDB
Ergosterol 5alpha ,8alpha -epidioxide	HMDB
Ergosterol endoperoxide	HMDB
ERGOSTEROL-5,8-peroxide	HMDB
O-(Trifluoromethyl)cinnamic acid	HMDB
Peroxyergosterol	HMDB
3-Hydroxy-5,7-epidioxyergosta-6,22-diene	MeSH
Ergosterol peroxide	MeSH
5,8-Epidioxyergosta-6,22-dien-3-ol	MeSH

Chemical Formula

C₂₈H₄₄O₃

Average Mass

428.6472 Da

Monoisotopic Mass

428.32905 Da

IUPAC Name

5-[(3E)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol

Traditional Name

5-[(3E)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol

CAS Registry Number

2061-64-5

SMILES

CC(C)C(C)\C=C\C(C)C1CCC2C1(C)CCC1C3(C)CCC(O)CC33OOC21C=C3

InChI Identifier

InChI=1S/C28H44O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,15-16,18-24,29H,9-14,17H2,1-6H3/b8-7+

InChI Key

VXOZCESVZIRHCJ-BQYQJAHWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ananas comosus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Andrographis paniculata	LOTUS Database	35616633
Aspergillus fumigatus	LOTUS Database	35616633
Aspergillus ochraceus	LOTUS Database	35616633
Benincasa hispida	LOTUS Database	35616633
Bombyx mori	LOTUS Database	35616633
Breynia fruticosa	LOTUS Database	35616633
Catathelasma ventricosa	Fungi	KNApSAcK
Catathelasma ventricosum	LOTUS Database	35616633
Cetraria islandica	LOTUS Database	35616633
Cetraria richardsonii	-	KNApSAcK
Chaetomium cochliodes	LOTUS Database	35616633
Chaetomium elatum	LOTUS Database	35616633
Chlorella vulgaris	LOTUS Database	35616633
Cladosporium sp.	Fungi	KNApSAcK
Cordyceps tenuipes	LOTUS Database	35616633
Daedalea quercina	LOTUS Database	35616633
Daedaleopsis confragosa var.tricolor	Fungi	KNApSAcK
Daedaleopsis quercina	Fungi	KNApSAcK
Degelia gayana	LOTUS Database	35616633
Diaporthe convolvuli	LOTUS Database	35616633
Duranta erecta	LOTUS Database	35616633
Duranta repens	Plant	KNApSAcK
Emericellopsis minima	LOTUS Database	35616633
Etlingera elatior	Plant	KNApSAcK
Ficus nervosa	LOTUS Database	35616633
Fomes fomentarius	LOTUS Database	35616633
Fomitopsis fomentarius	Fungi	KNApSAcK
Ganoderma applanatum	Fungi	KNApSAcK
Ganoderma australe	LOTUS Database	35616633
Ganoderma carnosum	Fungi	KNApSAcK
Ganoderma lucidum	Fungi	KNApSAcK
Ganoderma pfeifferi	LOTUS Database	35616633
Ganoderma sinense	LOTUS Database	35616633
Ganoderma tsugae	LOTUS Database	35616633
Grifola frondosa	LOTUS Database	35616633
Gynura japonica	LOTUS Database	35616633
Haloxylon salicornicum	LOTUS Database	35616633
Hericium erinaceus	LOTUS Database	35616633
Huperzia serrata	LOTUS Database	35616633
Hypholoma fasciculare	LOTUS Database	35616633
Hypholoma lateritium	LOTUS Database	35616633
Inonotus obliquus	LOTUS Database	35616633
Inula anatolica	LOTUS Database	35616633
Junceella fragilis	-	KNApSAcK
Lactarius hatsudake	LOTUS Database	35616633
Lactarius uvidus	LOTUS Database	35616633
Lactarius volemus	LOTUS Database	35616633
Laetiporus sulphureus	Fungi	KNApSAcK
Lethariella Lethariella cladonioides	LOTUS Database	35616633
Leucaena glauca	LOTUS Database	35616633
Leucoagaricus americanus	LOTUS Database	35616633
Lichtheimia corymbifera	LOTUS Database	35616633
Melia azedarach	LOTUS Database	35616633
Melilotus messanensis	LOTUS Database	35616633
Microporus affinis	LOTUS Database	35616633
Morchella esculenta	LOTUS Database	35616633
Nigrospora oryzae	LOTUS Database	35616633
Ochrolechia parella	-	KNApSAcK
Ophiocordyceps sinensis	LOTUS Database	35616633
Ovatospora brasiliensis	LOTUS Database	35616633
Panellus eryngii (DC.:FR.) QUEL.	Fungi	KNApSAcK
Pellia epiphylla	LOTUS Database	35616633
Penicillium chrysogenum	LOTUS Database	35616633
Penicillium commune	LOTUS Database	35616633
Penicillium oxalicum	LOTUS Database	35616633
Phaeolepiota aurea	LOTUS Database	35616633
Phellinus torulosus	LOTUS Database	35616633
Pisolithus arhizus	LOTUS Database	35616633
Pisolithus tinctorius	Fungi	KNApSAcK
Pisonia aculeata	LOTUS Database	35616633
Pleurotus eryngii	LOTUS Database	35616633
Podostictina encoensis	LOTUS Database	35616633
Polyporus tuberaster	LOTUS Database	35616633
Polyporus umbellatus	LOTUS Database	35616633
Porodaedalea pini	LOTUS Database	35616633
Psilocybe argentipes	LOTUS Database	35616633
Pulicaria canariensis	Plant	KNApSAcK
Ramalina hierrensis	LOTUS Database	35616633
Ramaria botrytis	LOTUS Database	35616633
Ramaria botrytis (Pers.) Ricken	Fungi	KNApSAcK
Rhizoplaca melanophthalma	LOTUS Database	35616633
Rhizopus oryzae	LOTUS Database	35616633
Rhynchosia minima	LOTUS Database	35616633
Russula subnigricans	LOTUS Database	35616633
Sarcodon aspratus	LOTUS Database	35616633
Sarcodon scabrosus	LOTUS Database	35616633
Saussurea hieracioides	LOTUS Database	35616633
Scleroderma polyrhizum	LOTUS Database	35616633
Scolochloa festucacea	LOTUS Database	35616633
Sinacalia tangutica	LOTUS Database	35616633
Sinularia flexibilis	LOTUS Database	35616633
Spiranthes sinensis	LOTUS Database	35616633
Staphylotrichum longicolle	LOTUS Database	35616633
Stereocaulon azoreum	LOTUS Database	35616633
Stereum hirsutum	LOTUS Database	35616633
Sticta weigelii	LOTUS Database	35616633
Taiwanofungus camphoratus	LOTUS Database	35616633
Teucrium heterophyllum	LOTUS Database	35616633
Thamnolia subuliformis	LOTUS Database	35616633
Thamnolia subuniformis	-	KNApSAcK
Thaxterogaster vibratilis	LOTUS Database	35616633
Trewia nudiflora	LOTUS Database	35616633
Tricholoma matsutake	LOTUS Database	35616633
Tuber indicum	LOTUS Database	35616633
Typha latifolia	LOTUS Database	35616633
Usnea articulata	LOTUS Database	35616633
Verbena officinalis	LOTUS Database	35616633
Xanthium strumarium	LOTUS Database	35616633
Zantedeschia aethiopica	LOTUS Database	35616633

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

Substituents

Ergostane-skeleton
Ortho-dioxane
Cyclic alcohol
Dialkyl peroxide
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

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	6.27	ALOGPS
logP	6.35	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	15.15	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	126.82 m³·mol⁻¹	ChemAxon
Polarizability	51.75 Å³	ChemAxon
Number of Rings	5	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

HMDB0037941

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017110

KNApSAcK ID

C00030200

Chemspider ID

4528211

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ergosterol peroxide

METLIN ID

Not Available

PubChem Compound

5379713

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dias DA, Urban S: HPLC and NMR studies of phenoxazone alkaloids from Pycnoporus cinnabarinus. Nat Prod Commun. 2009 Apr;4(4):489-98. [PubMed:19475991 ]
Duarte N, Ferreira MJ, Martins M, Viveiros M, Amaral L: Antibacterial activity of ergosterol peroxide against Mycobacterium tuberculosis: dependence upon system and medium employed. Phytother Res. 2007 Jul;21(7):601-4. doi: 10.1002/ptr.2119. [PubMed:17357175 ]

Showing NP-Card for Ergosterol peroxide (NP0048945)

MOL for NP0048945 (Ergosterol peroxide)

3D MOL for NP0048945 (Ergosterol peroxide)

3D SDF for NP0048945 (Ergosterol peroxide)

3D-SDF for NP0048945 (Ergosterol peroxide)

PDB for NP0048945 (Ergosterol peroxide)

3D PDB for NP0048945 (Ergosterol peroxide)

SMILES for NP0048945 (Ergosterol peroxide)

INCHI for NP0048945 (Ergosterol peroxide)

Structure for NP0048945 (Ergosterol peroxide)

3D Structure for NP0048945 (Ergosterol peroxide)