NP-MRD: Showing NP-Card for 6-O-Methylcerevisterol (NP0137945)

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Record Information

Version

2.0

Created at

2022-05-31 16:40:15 UTC

Updated at

2022-05-31 16:40:15 UTC

NP-MRD ID

NP0137945

Secondary Accession Numbers

NP0086477

Natural Product Identification

Common Name

6-O-Methylcerevisterol

Description

Blazein 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. Thus, blazein is considered to be a sterol. 6-O-Methylcerevisterol was first documented in 2008 (PMID: 19020714). Based on a literature review very few articles have been published on blazein (PMID: 21428374).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208462D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292208462D          

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  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  1  0  0  0
 15 20  1  6  0  0  0
 14 21  1  1  0  0  0
 11 22  1  1  0  0  0
  9 23  1  6  0  0  0
  8 24  1  1  0  0  0
 24 25  1  0  0  0  0
  5 26  1  6  0  0  0
  2 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 27 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0137945

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O3/c1-18(2)19(3)8-9-20(4)23-10-11-24-22-16-26(32-7)29(31)17-21(30)12-15-28(29,6)25(22)13-14-27(23,24)5/h8-9,16,18-21,23-26,30-31H,10-15,17H2,1-7H3/b9-8+/t19-,20+,21-,23+,24-,25-,26+,27+,28+,29-/m0/s1

> <INCHI_KEY>
GQVCGTRDXSDAHC-KNXFMRPFSA-N

> <FORMULA>
C29H48O3

> <MOLECULAR_WEIGHT>
444.7

> <EXACT_MASS>
444.360345406

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
53.95964990836865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,7R,8R,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-8-methoxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-ene-5,7-diol

> <ALOGPS_LOGP>
5.58

> <JCHEM_LOGP>
5.530023056000003

> <ALOGPS_LOGS>
-5.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.268732293331936

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.298521775273628

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7283110472323617

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
133.7249

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.72e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,7R,8R,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-8-methoxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-ene-5,7-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  H   UNK     0       4.215  -4.357   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      10.822  -2.707   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      12.861  -0.987   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      13.384   0.461   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0       8.783  -4.426   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.417  -8.505   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.998  -9.932   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.523 -10.142   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.053 -11.147   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.633 -12.574   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.527 -10.937   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18   27                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   18   26                                             
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8   10   14   23                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15   21                                             
CONECT   15   14    6   16   20                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    5    2   19                                             
CONECT   19   18                                                            
CONECT   20   15                                                            
CONECT   21   14                                                            
CONECT   22   11                                                            
CONECT   23    9                                                            
CONECT   24    8   25                                                       
CONECT   25   24                                                            
CONECT   26    5                                                            
CONECT   27    2   28   35                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   27                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₈O₃

Average Mass

444.7000 Da

Monoisotopic Mass

444.36035 Da

IUPAC Name

(1S,2R,5S,7R,8R,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-8-methoxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-ene-5,7-diol

Traditional Name

(1S,2R,5S,7R,8R,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-8-methoxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-ene-5,7-diol

CAS Registry Number

126060-09-1

SMILES

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

InChI Identifier

InChI=1S/C29H48O3/c1-18(2)19(3)8-9-20(4)23-10-11-24-22-16-26(32-7)29(31)17-21(30)12-15-28(29,6)25(22)13-14-27(23,24)5/h8-9,16,18-21,23-26,30-31H,10-15,17H2,1-7H3/b9-8+/t19-,20+,21-,23+,24-,25-,26+,27+,28+,29-/m0/s1

InChI Key

GQVCGTRDXSDAHC-KNXFMRPFSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:70337 )
ether (CHEBI:70337 )
5alpha-hydroxy steroid (CHEBI:70337 )
ergostanoid (CHEBI:70337 )

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	5.58	ALOGPS
logP	5.53	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	13.3	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	133.72 m³·mol⁻¹	ChemAxon
Polarizability	53.96 Å³	ChemAxon
Number of Rings	4	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00056761

Chemspider ID

29215786

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Blazein

METLIN ID

Not Available

PubChem Compound

14159790

PDB ID

Not Available

ChEBI ID

68081

Good Scents ID

Not Available

References

General References

Wu W, Dai H, Bao L, Ren B, Lu J, Luo Y, Guo L, Zhang L, Liu H: Isolation and structural elucidation of proline-containing cyclopentapeptides from an endolichenic Xylaria sp. J Nat Prod. 2011 May 27;74(5):1303-8. doi: 10.1021/np100909y. Epub 2011 Mar 23. [PubMed:21428374 ]
Itoh H, Ito H, Hibasami H: Blazein of a new steroid isolated from Agaricus blazei Murrill (himematsutake) induces cell death and morphological change indicative of apoptotic chromatin condensation in human lung cancer LU99 and stomach cancer KATO III cells. Oncol Rep. 2008 Dec;20(6):1359-61. [PubMed:19020714 ]

Showing NP-Card for 6-O-Methylcerevisterol (NP0137945)

MOL for NP0137945 (6-O-Methylcerevisterol)

3D MOL for NP0137945 (6-O-Methylcerevisterol)

3D SDF for NP0137945 (6-O-Methylcerevisterol)

3D-SDF for NP0137945 (6-O-Methylcerevisterol)

PDB for NP0137945 (6-O-Methylcerevisterol)

3D PDB for NP0137945 (6-O-Methylcerevisterol)

SMILES for NP0137945 (6-O-Methylcerevisterol)

INCHI for NP0137945 (6-O-Methylcerevisterol)

Structure for NP0137945 (6-O-Methylcerevisterol)

3D Structure for NP0137945 (6-O-Methylcerevisterol)