NP-MRD: Showing NP-Card for Stellasterol (NP0046638)

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Record Information

Version

2.0

Created at

2022-03-17 20:10:26 UTC

Updated at

2022-03-17 20:10:26 UTC

NP-MRD ID

NP0046638

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Stellasterol

Description

Stellasterol 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. Stellasterol is found in Acremonium coenophialum, Amelaria mellea, Aspergillus fennelliae, Aspergillus oryzae, Boletus luridus , Boletus spp. , Candida albicans, Candida sp., Candida tropicalis, Candida utilis, Coriolus pargamenus, Cryptoderma citrinum, Daedalea quercina, Flammulina velutipes , Fomes annosus, Fomes fomentarius, Piptoporus betulinus, Fomitopsis cytisina, Phellinus gilvus , Ganoderma amboinense, Ganoderma applanatum , Ganoderma australe, Ganoderma carnosum, Ganoderma lipsiense, Ganoderma lucidum , Ganoderma pfeifferi, Ganoderma sugae, Gloephyllum sepiarium, Hymenomycetes sp., Leccinum aurantiacum , Leccinum spp., Leptoshaeria maculans, Leptosphaeria typhae, Mikania micrantha , Neurospora crassa, Pholiota aegerita , Phycomyces blakesleeanus, Rhizopus arrhizus, Saccharomyces cerevisiae , Suillus bovinus , Suillus variegatus , Torulopsis glabrata, Coriolus versicolor , Tylopilus plumbeoviolaceus and Xanthoria parietina. Stellasterol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241223392D          

 29 32  0  0  0  0            999 V2000
    2.6865    0.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9477    1.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4006    1.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5923    1.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1064   -2.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6138   -3.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368   -2.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0418   -3.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7663   -2.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7663   -1.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403   -1.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368   -1.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3312    0.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8782    0.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6157   -0.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0954   -1.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6047   -1.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8211   -1.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1064   -1.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6125   -1.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6125   -0.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1121   -0.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8211   -0.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9230    0.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1160    3.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6618    2.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4700    2.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4700   -3.2109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 27  1  0  0  0  0
  5  6  1  0  0  0  0
  5 20  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 29  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
 12 21  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 24  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 24  1  0  0  0  0
 20 21  1  0  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
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END


  Mrv0541 02241223392D          

 29 32  0  0  0  0            999 V2000
    2.6865    0.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9477    1.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4006    1.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5923    1.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1064   -2.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6138   -3.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368   -2.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0418   -3.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7663   -2.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7663   -1.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403   -1.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368   -1.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3312    0.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8782    0.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6157   -0.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0954   -1.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6047   -1.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8211   -1.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1064   -1.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6125   -1.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6125   -0.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1121   -0.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8211   -0.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9230    0.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1160    3.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6618    2.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4700    2.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4700   -3.2109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 27  1  0  0  0  0
  5  6  1  0  0  0  0
  5 20  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 29  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
 12 21  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 24  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 24  1  0  0  0  0
 20 21  1  0  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
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046638

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(C)\C=C/C(C)C1CCC2C3=CCC4CC(O)CCC4(C)C3CCC12C

> <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/h7-8,10,18-22,24-26,29H,9,11-17H2,1-6H3/b8-7-

> <INCHI_KEY>
QOXPZVASXWSKKU-FPLPWBNLSA-N

> <FORMULA>
C28H46O

> <MOLECULAR_WEIGHT>
398.6642

> <EXACT_MASS>
398.354866094

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
50.33956519407704

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-[(3Z)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

> <ALOGPS_LOGP>
7.13

> <JCHEM_LOGP>
7.037986470333335

> <ALOGPS_LOGS>
-6.95

> <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>
126.28169999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.44e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-[(3Z)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-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       5.015   0.811   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.502   2.271   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.481   3.423   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.972   3.115   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.199  -5.257   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.146  -6.035   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.495  -5.255   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.811  -6.014   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.164  -5.234   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.164  -3.672   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.809  -2.892   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.495  -3.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.495  -2.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.485   1.655   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.506   0.503   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.016  -0.957   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.911  -2.209   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.995  -3.448   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.533  -2.953   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.199  -3.723   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.143  -2.915   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.143  -1.398   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.209  -0.616   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.533  -1.419   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.723   0.110   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.950   6.035   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.969   4.883   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.477   5.190   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -6.477  -5.994   0.000  0.00  0.00           O+0
CONECT    1    2   15                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3                                                            
CONECT    5    6   20                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   29                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    7   11   13   21                                             
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15    1   14   16                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20    5   19   21                                                  
CONECT   21   12   20   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   16   19   23   25                                             
CONECT   25   24                                                            
CONECT   26   27                                                            
CONECT   27    3   26   28                                                  
CONECT   28   27                                                            
CONECT   29    9                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₆O

Average Mass

398.6642 Da

Monoisotopic Mass

398.35487 Da

IUPAC Name

14-[(3Z)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

Traditional Name

14-[(3Z)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

CAS Registry Number

Not Available

SMILES

CC(C)C(C)\C=C/C(C)C1CCC2C3=CCC4CC(O)CCC4(C)C3CCC12C

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/h7-8,10,18-22,24-26,29H,9,11-17H2,1-6H3/b8-7-

InChI Key

QOXPZVASXWSKKU-FPLPWBNLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acremonium coenophialum	Fungi	KNApSAcK
Amelaria mellea	-	KNApSAcK
Aspergillus fennelliae	Fungi	KNApSAcK
Aspergillus oryzae	Fungi	KNApSAcK
Boletus luridus	Fungi	KNApSAcK
Boletus spp.	Fungi	KNApSAcK
Candida albicans	Fungi	KNApSAcK
Candida sp.	Fungi	KNApSAcK
Candida tropicalis	Fungi	KNApSAcK
Candida utilis	Fungi	KNApSAcK
Coriolus pargamenus	Fungi	KNApSAcK
Cryptoderma citrinum	-	KNApSAcK
Cucumis sativus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daedalea quercina	Fungi	KNApSAcK
Flammulina velutipes	Fungi	KNApSAcK
Fomes annosus	Fungi	KNApSAcK
Fomes fomentarius	Fungi	KNApSAcK
Fomitopsis betulina	Fungi	KNApSAcK
Fomitopsis cytisina	Fungi	KNApSAcK
Fuscoporia gilva	Fungi	KNApSAcK
Ganoderma amboinense	Fungi	KNApSAcK
Ganoderma applanatum	Fungi	KNApSAcK
Ganoderma australe	Fungi	KNApSAcK
Ganoderma carnosum	Fungi	KNApSAcK
Ganoderma lipsiense	Fungi	KNApSAcK
Ganoderma lucidum	Fungi	KNApSAcK
Ganoderma pfeifferi	Fungi	KNApSAcK
Ganoderma sugae	Fungi	KNApSAcK
Gloephyllum sepiarium	-	KNApSAcK
Hymenomycetes sp.	-	KNApSAcK
Leccinum aurantiacum	Fungi	KNApSAcK
Leccinum spp.	Fungi	KNApSAcK
Leptoshaeria maculans	-	KNApSAcK
Leptosphaeria typhae	Fungi	KNApSAcK
Mikania micrantha	Plant	KNApSAcK
Neurospora crassa	Fungi	KNApSAcK
Pholiota aegerita	Fungi	KNApSAcK
Phycomyces blakesleeanus	Fungi	KNApSAcK
Rhizopus oryzae	Fungi	KNApSAcK
Saccharomyces cerevisiae	Fungi	KNApSAcK
Suillus bovinus	Fungi	KNApSAcK
Suillus variegatus	Fungi	KNApSAcK
Torulopsis glabrata	Fungi	KNApSAcK
Trametes Versicolor	Fungi	KNApSAcK
Tylopilus plumbeoviolaceus	Fungi	KNApSAcK
Xanthoria parietina	Fungi	KNApSAcK

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
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

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	7.13	ALOGPS
logP	7.04	ChemAxon
logS	-7	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	4	ChemAxon
Refractivity	126.28 m³·mol⁻¹	ChemAxon
Polarizability	50.34 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB005294

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

5358162

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Stellasterol (NP0046638)

MOL for NP0046638 (Stellasterol)

3D MOL for NP0046638 (Stellasterol)

3D SDF for NP0046638 (Stellasterol)

3D-SDF for NP0046638 (Stellasterol)

PDB for NP0046638 (Stellasterol)

3D PDB for NP0046638 (Stellasterol)

SMILES for NP0046638 (Stellasterol)

INCHI for NP0046638 (Stellasterol)

Structure for NP0046638 (Stellasterol)

3D Structure for NP0046638 (Stellasterol)