NP-MRD: Showing NP-Card for 5,8-Epidioxyergosta-6,9(11),22-trien-3-ol (NP0137944)

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Record Information

Version

2.0

Created at

2022-05-31 16:40:12 UTC

Updated at

2022-05-31 16:40:13 UTC

NP-MRD ID

NP0137944

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,8-Epidioxyergosta-6,9(11),22-trien-3-ol

Description

9,11-Dehydroergosterol peroxide, also known as 5,8-edeto, 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. Thus, 9,11-dehydroergosterol peroxide is considered to be a sterol. 5,8-Epidioxyergosta-6,9(11),22-trien-3-ol is found in Duranta erecta, Ganoderma applanatum, Ganoderma tsugae, Grifola frondosa, Haloxylon salicornicum, Ophiocordyceps sinensis, Pellia epiphylla, Sinularia flexibilis, Stereum hirsutum, Mallotus nudiflorus and Typha capensis. 5,8-Epidioxyergosta-6,9(11),22-trien-3-ol was first documented in 2017 (PMID: 28315853). Based on a literature review a small amount of articles have been published on 9,11-dehydroergosterol peroxide (PMID: 30149516) (PMID: 30092384) (PMID: 30560887) (PMID: 29845223).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312218402D          

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  Mrv1652305312218402D          

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   -5.2625    1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535    2.9911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  1  0  0  0
  8  5  1  6  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 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
 23 24  1  1  0  0  0
 23 25  1  6  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 30 29  1  1  0  0  0
 12 30  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  6  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137944

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])[C@@]([H])(C)[C@@]1([H])CC[C@]2([H])[C@]1(C)CC=C1[C@@]3(C)CC[C@]([H])(O)C[C@@]33OO[C@@]21C=C3)[C@]([H])(C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O3/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/h7-8,12,15-16,18-23,29H,9-11,13-14,17H2,1-6H3/b8-7+/t19-,20+,21-,22+,23+,25+,26+,27+,28-/m0/s1

> <INCHI_KEY>
FWPYIYVSYQRISA-LEOBWYFPSA-N

> <FORMULA>
C28H42O3

> <MOLECULAR_WEIGHT>
426.641

> <EXACT_MASS>
426.313395212

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
51.87553218384816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5R,6R,10R,13S,15S)-5-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0^{1,9}.0^{2,6}.0^{10,15}]nonadeca-8,18-dien-13-ol

> <JCHEM_LOGP>
6.020313096333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.14787838866792

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7341179927966524

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
127.59709999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5R,6R,10R,13S,15S)-5-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0^{1,9}.0^{2,6}.0^{10,15}]nonadeca-8,18-dien-13-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  H   UNK     0      -5.362   4.897   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -5.759   3.409   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.668   2.321   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0      -5.065   0.833   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0      -3.181   2.722   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0      -4.272   3.809   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0      -2.785   4.210   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.091   1.634   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0      -3.555   1.156   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0      -2.330   0.113   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.957  -0.584   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.131   0.506   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       1.115   1.691   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0      -0.570   1.878   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.360   3.200   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.386   3.130   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.915   2.841   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.577   1.394   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.155   1.012   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.768   2.503   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.330   2.097   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.887   1.905   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.346   0.404   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       7.608  -1.113   0.000  0.00  0.00           H+0
HETATM   25  O   UNK     0       8.812  -0.067   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.089  -0.556   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.478  -0.606   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.076  -1.753   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.506  -1.527   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.670   0.051   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.126  -0.640   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.202  -2.031   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -7.246   3.008   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0      -6.155   1.920   0.000  0.00  0.00           H+0
HETATM   35  C   UNK     0      -7.642   1.520   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -8.336   4.095   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -9.823   3.695   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -7.940   5.583   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9   10   14                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   30                                             
CONECT   13   12                                                            
CONECT   14   12    8   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   30                                                  
CONECT   19   18   20   21   27                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27                                                       
CONECT   27   26   19   28   32                                             
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   12   18   31                                             
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33    2   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
5,8-EDETO	MeSH

Chemical Formula

C₂₈H₄₂O₃

Average Mass

426.6410 Da

Monoisotopic Mass

426.31340 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

86363-50-0

SMILES

[H]\C(=C(\[H])[C@@]([H])(C)[C@@]1([H])CC[C@]2([H])[C@]1(C)CC=C1[C@@]3(C)CC[C@]([H])(O)C[C@@]33OO[C@@]21C=C3)[C@]([H])(C)C(C)C

InChI Identifier

InChI=1S/C28H42O3/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/h7-8,12,15-16,18-23,29H,9-11,13-14,17H2,1-6H3/b8-7+/t19-,20+,21-,22+,23+,25+,26+,27+,28-/m0/s1

InChI Key

FWPYIYVSYQRISA-LEOBWYFPSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Duranta erecta	LOTUS Database	35616633
Ganoderma applanatum	LOTUS Database	35616633
Ganoderma tsugae	LOTUS Database	35616633
Grifola frondosa	LOTUS Database	35616633
Haloxylon salicornicum	LOTUS Database	35616633
Ophiocordyceps sinensis	LOTUS Database	35616633
Pellia epiphylla	LOTUS Database	35616633
Sinularia flexibilis	LOTUS Database	35616633
Stereum hirsutum	LOTUS Database	35616633
Trewia nudiflora	LOTUS Database	35616633
Typha capensis	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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9287871

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11112737

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lee S, Lee S, Roh HS, Song SS, Ryoo R, Pang C, Baek KH, Kim KH: Cytotoxic Constituents from the Sclerotia of Poria cocos against Human Lung Adenocarcinoma Cells by Inducing Mitochondrial Apoptosis. Cells. 2018 Aug 24;7(9). pii: cells7090116. doi: 10.3390/cells7090116. [PubMed:30149516 ]
Lee S, Choi E, Yang SM, Ryoo R, Moon E, Kim SH, Kim KH: Bioactive compounds from sclerotia extract of Poria cocos that control adipocyte and osteoblast differentiation. Bioorg Chem. 2018 Dec;81:27-34. doi: 10.1016/j.bioorg.2018.07.031. Epub 2018 Jul 31. [PubMed:30092384 ]
Wu HY, Yang FL, Li LH, Rao YK, Ju TC, Wong WT, Hsieh CY, Pivkin MV, Hua KF, Wu SH: Ergosterol peroxide from marine fungus Phoma sp. induces ROS-dependent apoptosis and autophagy in human lung adenocarcinoma cells. Sci Rep. 2018 Dec 18;8(1):17956. doi: 10.1038/s41598-018-36411-2. [PubMed:30560887 ]
Zheng L, Wong YS, Shao M, Huang S, Wang F, Chen J: Apoptosis induced by 9,11dehydroergosterol peroxide from Ganoderma Lucidum mycelium in human malignant melanoma cells is Mcl1 dependent. Mol Med Rep. 2018 Jul;18(1):938-944. doi: 10.3892/mmr.2018.9035. Epub 2018 May 17. [PubMed:29845223 ]
Merdivan S, Jenett-Siems K, Siems K, Niedermeyer THJ, Schultze N, Steinborn C, Grundemann C, Lindequist U: Effects of extracts and compounds from Tricholoma populinum Lange on degranulation and IL-2/IL-8 secretion of immune cells. Z Naturforsch C J Biosci. 2017 Jul 14;72(7-8):277-283. doi: 10.1515/znc-2016-0247. [PubMed:28315853 ]

Showing NP-Card for 5,8-Epidioxyergosta-6,9(11),22-trien-3-ol (NP0137944)

MOL for NP0137944 (5,8-Epidioxyergosta-6,9(11),22-trien-3-ol)

3D MOL for NP0137944 (5,8-Epidioxyergosta-6,9(11),22-trien-3-ol)

3D SDF for NP0137944 (5,8-Epidioxyergosta-6,9(11),22-trien-3-ol)

3D-SDF for NP0137944 (5,8-Epidioxyergosta-6,9(11),22-trien-3-ol)

PDB for NP0137944 (5,8-Epidioxyergosta-6,9(11),22-trien-3-ol)

3D PDB for NP0137944 (5,8-Epidioxyergosta-6,9(11),22-trien-3-ol)

SMILES for NP0137944 (5,8-Epidioxyergosta-6,9(11),22-trien-3-ol)

INCHI for NP0137944 (5,8-Epidioxyergosta-6,9(11),22-trien-3-ol)

Structure for NP0137944 (5,8-Epidioxyergosta-6,9(11),22-trien-3-ol)

3D Structure for NP0137944 (5,8-Epidioxyergosta-6,9(11),22-trien-3-ol)