NP-MRD: Showing NP-Card for (3beta,5alpha,6beta,9alpha,22E,24R)-5,9-Epidioxyergosta-7,22-diene-3,6-diol (NP0335797)

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Record Information

Version

2.0

Created at

2024-09-11 03:16:55 UTC

Updated at

2024-09-11 03:16:56 UTC

NP-MRD ID

NP0335797

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3beta,5alpha,6beta,9alpha,22E,24R)-5,9-Epidioxyergosta-7,22-diene-3,6-diol

Description

(3Beta,5alpha,6beta,9alpha,22E,24R)-5,9-Epidioxyergosta-7,22-diene-3,6-diol 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. Based on a literature review very few articles have been published on (3beta,5alpha,6beta,9alpha,22E,24R)-5,9-Epidioxyergosta-7,22-diene-3,6-diol.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262305492D          

 32 36  0  0  0  0            999 V2000
   -3.6039   -0.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6039   -1.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8897   -1.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1769   -1.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1769   -0.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8897   -0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628   -1.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7498   -1.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7498   -0.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628   -0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0386   -0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0386    0.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7498    0.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628    0.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7415   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2218    0.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7415    0.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1769    0.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1769   -2.3936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628   -1.1565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628   -2.8064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3194   -1.9808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0386    1.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7415    1.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0261    1.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4571    1.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1726    1.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8883    1.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6039    1.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8883    2.8064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3194    1.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6039    0.7422    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 22  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 19  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 18  1  0  0  0  0
  7  8  1  0  0  0  0
  7 21  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 10 20  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 23  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 24  1  0  0  0  0
 19 20  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
M  END


  Mrv2104 05262305492D          

 32 36  0  0  0  0            999 V2000
   -3.6039   -0.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6039   -1.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8897   -1.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1769   -1.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1769   -0.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8897   -0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628   -1.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7498   -1.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7498   -0.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628   -0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0386   -0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0386    0.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7498    0.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628    0.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7415   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2218    0.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7415    0.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1769    0.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1769   -2.3936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628   -1.1565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4628   -2.8064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3194   -1.9808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0386    1.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7415    1.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0261    1.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4571    1.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1726    1.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8883    1.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6039    1.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8883    2.8064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3194    1.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6039    0.7422    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 22  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 19  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 18  1  0  0  0  0
  7  8  1  0  0  0  0
  7 21  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 10 20  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 23  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 24  1  0  0  0  0
 19 20  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335797

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(C)\C=C\C(C)C1CCC2C3=CC(O)C45CC(O)CCC4(C)C3(CCC12C)OO5

> <INCHI_IDENTIFIER>
InChI=1/C28H44O4/c1-17(2)18(3)7-8-19(4)21-9-10-22-23-15-24(30)28-16-20(29)11-12-26(28,6)27(23,31-32-28)14-13-25(21,22)5/h7-8,15,17-22,24,29-30H,9-14,16H2,1-6H3/b8-7+

> <INCHI_KEY>
XCRHWCBOUDKLGM-BQYQJAHWNA-N

> <FORMULA>
C28H44O4

> <MOLECULAR_WEIGHT>
444.656

> <EXACT_MASS>
444.323959897

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
52.455617060809494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-[(3E)-5,6-dimethylhept-3-en-2-yl]-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0^{1,13}.0^{4,12}.0^{5,9}]nonadec-3-ene-2,16-diol

> <JCHEM_LOGP>
5.229377415999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.169677950727518

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.453051305092183

> <JCHEM_PKA_STRONGEST_BASIC>
-2.731290462382888

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
127.91899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
8-[(3E)-5,6-dimethylhept-3-en-2-yl]-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0^{1,13}.0^{4,12}.0^{5,9}]nonadec-3-ene-2,16-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -6.727  -1.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.727  -2.927   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.394  -3.697   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.064  -2.927   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.064  -1.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.394  -0.618   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.731  -3.697   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.400  -2.927   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.400  -1.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.731  -0.618   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.072  -0.618   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.072   0.916   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.400   1.681   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.731   0.916   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.384  -1.090   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.281   0.150   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.384   1.385   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.064   0.155   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.064  -4.468   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.731  -2.159   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.731  -5.239   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -8.063  -3.697   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.072   2.457   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.384   2.927   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.049   3.697   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.720   3.697   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.056   2.927   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.391   3.697   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.727   2.927   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.391   5.239   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.063   3.697   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.727   1.385   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   19                                             
CONECT    5    4    6   10   18                                             
CONECT    6    1    5                                                       
CONECT    7    4    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14   20                                             
CONECT   11    9   12   15                                                  
CONECT   12   11   13   17   23                                             
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16   24                                                  
CONECT   18    5                                                            
CONECT   19    4   20                                                       
CONECT   20   10   19                                                       
CONECT   21    7                                                            
CONECT   22    2                                                            
CONECT   23   12                                                            
CONECT   24   17   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28   31   32                                                  
CONECT   30   28                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
(3b,5a,6b,9a,22E,24R)-5,9-Epidioxyergosta-7,22-diene-3,6-diol	Generator
(3Β,5α,6β,9α,22E,24R)-5,9-epidioxyergosta-7,22-diene-3,6-diol	Generator

Chemical Formula

C₂₈H₄₄O₄

Average Mass

444.6560 Da

Monoisotopic Mass

444.32396 Da

IUPAC Name

8-[(3E)-5,6-dimethylhept-3-en-2-yl]-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0^{1,13}.0^{4,12}.0^{5,9}]nonadec-3-ene-2,16-diol

Traditional Name

8-[(3E)-5,6-dimethylhept-3-en-2-yl]-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0^{1,13}.0^{4,12}.0^{5,9}]nonadec-3-ene-2,16-diol

CAS Registry Number

Not Available

SMILES

CC(C)C(C)\C=C\C(C)C1CCC2C3=CC(O)C45CC(O)CCC4(C)C3(CCC12C)OO5

InChI Identifier

InChI=1/C28H44O4/c1-17(2)18(3)7-8-19(4)21-9-10-22-23-15-24(30)28-16-20(29)11-12-26(28,6)27(23,31-32-28)14-13-25(21,22)5/h7-8,15,17-22,24,29-30H,9-14,16H2,1-6H3/b8-7+

InChI Key

XCRHWCBOUDKLGM-BQYQJAHWNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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
Cyclic alcohol
Ortho-dioxolane
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	5.23	ChemAxon
pKa (Strongest Acidic)	13.45	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	127.92 m³·mol⁻¹	ChemAxon
Polarizability	52.46 Å³	ChemAxon
Number of Rings	5	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

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References

General References

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Showing NP-Card for (3beta,5alpha,6beta,9alpha,22E,24R)-5,9-Epidioxyergosta-7,22-diene-3,6-diol (NP0335797)

MOL for NP0335797 ((3beta,5alpha,6beta,9alpha,22E,24R)-5,9-Epidioxyergosta-7,22-diene-3,6-diol)

3D MOL for NP0335797 ((3beta,5alpha,6beta,9alpha,22E,24R)-5,9-Epidioxyergosta-7,22-diene-3,6-diol)

3D SDF for NP0335797 ((3beta,5alpha,6beta,9alpha,22E,24R)-5,9-Epidioxyergosta-7,22-diene-3,6-diol)

3D-SDF for NP0335797 ((3beta,5alpha,6beta,9alpha,22E,24R)-5,9-Epidioxyergosta-7,22-diene-3,6-diol)

PDB for NP0335797 ((3beta,5alpha,6beta,9alpha,22E,24R)-5,9-Epidioxyergosta-7,22-diene-3,6-diol)

3D PDB for NP0335797 ((3beta,5alpha,6beta,9alpha,22E,24R)-5,9-Epidioxyergosta-7,22-diene-3,6-diol)

SMILES for NP0335797 ((3beta,5alpha,6beta,9alpha,22E,24R)-5,9-Epidioxyergosta-7,22-diene-3,6-diol)

INCHI for NP0335797 ((3beta,5alpha,6beta,9alpha,22E,24R)-5,9-Epidioxyergosta-7,22-diene-3,6-diol)

Structure for NP0335797 ((3beta,5alpha,6beta,9alpha,22E,24R)-5,9-Epidioxyergosta-7,22-diene-3,6-diol)

3D Structure for NP0335797 ((3beta,5alpha,6beta,9alpha,22E,24R)-5,9-Epidioxyergosta-7,22-diene-3,6-diol)