NP-MRD: Showing NP-Card for (3beta,5alpha,6beta,7alpha,22E,24R)-Ergosta-8,22-diene-3,5,6,7-tetrol (NP0047369)

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Record Information

Version

2.0

Created at

2022-03-17 20:39:04 UTC

Updated at

2022-03-17 20:39:04 UTC

NP-MRD ID

NP0047369

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3beta,5alpha,6beta,7alpha,22E,24R)-Ergosta-8,22-diene-3,5,6,7-tetrol

Description

(3Beta,5alpha,6beta,7alpha,22E,24R)-Ergosta-8,22-diene-3,5,6,7-tetrol 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 (3beta,5alpha,6beta,7alpha,22E,24R)-Ergosta-8,22-diene-3,5,6,7-tetrol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (3beta,5alpha,6beta,7alpha,22E,24R)-ergosta-8,22-diene-3,5,6,7-tetrol has been detected, but not quantified in, mushrooms. This could make (3beta,5alpha,6beta,7alpha,22E,24R)-ergosta-8,22-diene-3,5,6,7-tetrol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306222D          

 32 35  0  0  0  0            999 V2000
    8.0438   -0.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9157   -1.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0311    0.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685   -0.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083    0.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924    0.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9030   -0.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3966    0.5575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024    1.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6195    2.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5318    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9045    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167    0.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2266   -0.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7202    0.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5794    0.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8121    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0730    1.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682    1.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242    1.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1561    1.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8758    2.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636    2.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2485    1.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8121    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5318    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242    1.9404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4076    3.3969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7833    3.6873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515    3.0566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0  0  0  0
 10  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 17  3  1  0  0  0  0
 17  7  1  0  0  0  0
 17 16  1  0  0  0  0
 18  4  1  0  0  0  0
 18  8  1  0  0  0  0
 19 11  1  0  0  0  0
 19 15  1  0  0  0  0
 20  9  1  0  0  0  0
 20 18  1  0  0  0  0
 21 10  1  0  0  0  0
 22 12  1  0  0  0  0
 23 21  1  0  0  0  0
 23 22  2  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26  5  1  0  0  0  0
 26 13  1  0  0  0  0
 26 20  1  0  0  0  0
 26 21  1  0  0  0  0
 27  6  1  0  0  0  0
 27 14  1  0  0  0  0
 27 22  1  0  0  0  0
 28 15  1  0  0  0  0
 28 25  1  0  0  0  0
 28 27  1  0  0  0  0
 29 19  1  0  0  0  0
 30 24  1  0  0  0  0
 31 25  1  0  0  0  0
 32 28  1  0  0  0  0
M  END


  Mrv0541 05061306222D          

 32 35  0  0  0  0            999 V2000
    8.0438   -0.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9157   -1.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0311    0.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685   -0.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083    0.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924    0.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9030   -0.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3966    0.5575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024    1.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6195    2.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5318    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9045    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167    0.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2266   -0.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7202    0.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5794    0.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8121    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0730    1.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682    1.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242    1.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1561    1.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8758    2.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636    2.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2485    1.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8121    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5318    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242    1.9404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4076    3.3969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7833    3.6873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515    3.0566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0  0  0  0
 10  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 17  3  1  0  0  0  0
 17  7  1  0  0  0  0
 17 16  1  0  0  0  0
 18  4  1  0  0  0  0
 18  8  1  0  0  0  0
 19 11  1  0  0  0  0
 19 15  1  0  0  0  0
 20  9  1  0  0  0  0
 20 18  1  0  0  0  0
 21 10  1  0  0  0  0
 22 12  1  0  0  0  0
 23 21  1  0  0  0  0
 23 22  2  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26  5  1  0  0  0  0
 26 13  1  0  0  0  0
 26 20  1  0  0  0  0
 26 21  1  0  0  0  0
 27  6  1  0  0  0  0
 27 14  1  0  0  0  0
 27 22  1  0  0  0  0
 28 15  1  0  0  0  0
 28 25  1  0  0  0  0
 28 27  1  0  0  0  0
 29 19  1  0  0  0  0
 30 24  1  0  0  0  0
 31 25  1  0  0  0  0
 32 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047369

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(C)\C=C\C(C)C1CCC2C3=C(CCC12C)C1(C)CCC(O)CC1(O)C(O)C3O

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O4/c1-16(2)17(3)7-8-18(4)20-9-10-21-23-22(12-13-26(20,21)5)27(6)14-11-19(29)15-28(27,32)25(31)24(23)30/h7-8,16-21,24-25,29-32H,9-15H2,1-6H3/b8-7+

> <INCHI_KEY>
JYZONTNDJOOGSM-BQYQJAHWSA-N

> <FORMULA>
C28H46O4

> <MOLECULAR_WEIGHT>
446.6624

> <EXACT_MASS>
446.33960996

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
53.29463381944042

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-[(3E)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-5,7,8,9-tetrol

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
3.768335120666666

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.806829066324521

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.707035850316412

> <JCHEM_PKA_STRONGEST_BASIC>
-2.728591227683218

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
130.06859999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-[(3E)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-5,7,8,9-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      15.015  -0.970   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.909  -2.607   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.125   1.462   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.968  -0.597   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.735   0.610   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.039   1.361   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.019  -0.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.074   1.041   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.031   3.525   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.756   4.389   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.993   1.903   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.555   1.089   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.071   0.818   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.523   1.632   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.523   4.528   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.490  -1.180   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.544   0.035   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.548   0.830   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.516   3.351   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.603   2.046   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.541   3.444   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.032   2.538   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.025   3.715   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.501   5.164   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.985   5.435   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.064   1.996   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.516   2.809   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.993   4.257   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.032   3.622   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.494   6.341   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.462   6.883   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.469   5.706   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5   26                                                            
CONECT    6   27                                                            
CONECT    7    8   17                                                       
CONECT    8    7   18                                                       
CONECT    9   10   20                                                       
CONECT   10    9   21                                                       
CONECT   11   14   19                                                       
CONECT   12   13   22                                                       
CONECT   13   12   26                                                       
CONECT   14   11   27                                                       
CONECT   15   19   28                                                       
CONECT   16    1    2   17                                                  
CONECT   17    3    7   16                                                  
CONECT   18    4    8   20                                                  
CONECT   19   11   15   29                                                  
CONECT   20    9   18   26                                                  
CONECT   21   10   23   26                                                  
CONECT   22   12   23   27                                                  
CONECT   23   21   22   24                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   28   31                                                  
CONECT   26    5   13   20   21                                             
CONECT   27    6   14   22   28                                             
CONECT   28   15   25   27   32                                             
CONECT   29   19                                                            
CONECT   30   24                                                            
CONECT   31   25                                                            
CONECT   32   28                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(3b,5a,6b,7a,22E,24R)-Ergosta-8,22-diene-3,5,6,7-tetrol	Generator
(3Β,5α,6β,7α,22E,24R)-ergosta-8,22-diene-3,5,6,7-tetrol	Generator

Chemical Formula

C₂₈H₄₆O₄

Average Mass

446.6624 Da

Monoisotopic Mass

446.33961 Da

IUPAC Name

14-[(3E)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-5,7,8,9-tetrol

Traditional Name

14-[(3E)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-5,7,8,9-tetrol

CAS Registry Number

200942-15-0

SMILES

CC(C)C(C)\C=C\C(C)C1CCC2C3=C(CCC12C)C1(C)CCC(O)CC1(O)C(O)C3O

InChI Identifier

InChI=1S/C28H46O4/c1-16(2)17(3)7-8-18(4)20-9-10-21-23-22(12-13-26(20,21)5)27(6)14-11-19(29)15-28(27,32)25(31)24(23)30/h7-8,16-21,24-25,29-32H,9-15H2,1-6H3/b8-7+

InChI Key

JYZONTNDJOOGSM-BQYQJAHWSA-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 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

Not Available

Substituents

Not Available

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	3.84	ALOGPS
logP	3.77	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	12.71	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	130.07 m³·mol⁻¹	ChemAxon
Polarizability	53.29 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0032107

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008828

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

131751259

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (3beta,5alpha,6beta,7alpha,22E,24R)-Ergosta-8,22-diene-3,5,6,7-tetrol (NP0047369)

MOL for NP0047369 ((3beta,5alpha,6beta,7alpha,22E,24R)-Ergosta-8,22-diene-3,5,6,7-tetrol)

3D MOL for NP0047369 ((3beta,5alpha,6beta,7alpha,22E,24R)-Ergosta-8,22-diene-3,5,6,7-tetrol)

3D SDF for NP0047369 ((3beta,5alpha,6beta,7alpha,22E,24R)-Ergosta-8,22-diene-3,5,6,7-tetrol)

3D-SDF for NP0047369 ((3beta,5alpha,6beta,7alpha,22E,24R)-Ergosta-8,22-diene-3,5,6,7-tetrol)

PDB for NP0047369 ((3beta,5alpha,6beta,7alpha,22E,24R)-Ergosta-8,22-diene-3,5,6,7-tetrol)

3D PDB for NP0047369 ((3beta,5alpha,6beta,7alpha,22E,24R)-Ergosta-8,22-diene-3,5,6,7-tetrol)

SMILES for NP0047369 ((3beta,5alpha,6beta,7alpha,22E,24R)-Ergosta-8,22-diene-3,5,6,7-tetrol)

INCHI for NP0047369 ((3beta,5alpha,6beta,7alpha,22E,24R)-Ergosta-8,22-diene-3,5,6,7-tetrol)

Structure for NP0047369 ((3beta,5alpha,6beta,7alpha,22E,24R)-Ergosta-8,22-diene-3,5,6,7-tetrol)

3D Structure for NP0047369 ((3beta,5alpha,6beta,7alpha,22E,24R)-Ergosta-8,22-diene-3,5,6,7-tetrol)