NP-MRD: Showing NP-Card for Ergosta-5,7,22,24(28)-tetraen-3beta-ol (NP0066359)

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Record Information

Version

2.0

Created at

2022-04-28 10:38:14 UTC

Updated at

2022-04-28 10:38:14 UTC

NP-MRD ID

NP0066359

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ergosta-5,7,22,24(28)-tetraen-3beta-ol

Description

Ergosta-5,7,22,24(28)-tetraen-3-β-ol, also known as 5,7,22,24(28)-ergostatetraenol, 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, ergosta-5,7,22,24(28)-tetraen-3-β-ol is considered to be a sterol lipid molecule. Ergosta-5,7,22,24(28)-tetraen-3beta-ol is found in Aspergillus oryzae, Candida albicans, Candida utilis, Cyanidium caldarium, Gibberella fujikuroi and Saccharomyces cerevisiae . Ergosta-5,7,22,24(28)-tetraen-3-β-ol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

ChEBI
  Mrv0541 02241222272D          

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M  END

     RDKit          3D

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M  END

ChEBI
  Mrv0541 02241222272D          

 32 35  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0066359

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=C)\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O/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/h7-10,18,20,22,24-26,29H,3,11-17H2,1-2,4-6H3/b8-7+/t20-,22+,24-,25+,26+,27+,28-/m1/s1

> <INCHI_KEY>
SQFQJKZSFOZDJY-CVGLIYDESA-N

> <FORMULA>
C28H42O

> <MOLECULAR_WEIGHT>
394.6325

> <EXACT_MASS>
394.323565966

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
50.40834530020503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R,3E)-6-methyl-5-methylidenehept-3-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol

> <ALOGPS_LOGP>
7.48

> <JCHEM_LOGP>
6.284761178000001

> <ALOGPS_LOGS>
-5.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.270805421445605

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3681497086596925

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
126.90919999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.28e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7,22,24(28)-ergostatetraenol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ChEBI                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      13.026 -15.353   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.675 -16.089   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.675 -17.645   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.026 -18.415   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.343 -17.645   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.677 -18.415   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.028 -17.645   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.028 -16.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.677 -15.353   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.343 -16.089   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.677 -13.831   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.028 -13.045   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.345 -13.831   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.345 -15.353   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.816 -15.815   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.688 -14.601   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.816 -13.369   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.345 -12.258   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.343 -14.584   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.816 -11.779   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.396 -10.818   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.167 -10.975   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.483 -11.728   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.817 -10.924   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      25.151 -11.676   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      25.151 -13.233   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      26.468 -10.873   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      23.783  -9.385   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      18.345 -16.892   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      15.677 -16.892   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      21.149 -12.600   0.000  0.00  0.00           H+0
HETATM   32  O   UNK     0      10.432 -18.278   0.000  0.00  0.00           O+0
CONECT    1   10    2                                                       
CONECT    2    1    3                                                       
CONECT    3    4    2   32                                                  
CONECT    4    5    3                                                       
CONECT    5   10    4    6                                                  
CONECT    6    7    5                                                       
CONECT    7    8    6                                                       
CONECT    8   14    9    7                                                  
CONECT    9   11   10    8   30                                             
CONECT   10    9    5   19    1                                             
CONECT   11    9   12                                                       
CONECT   12   13   11                                                       
CONECT   13   14   17   12   18                                             
CONECT   14   13    8   15   29                                             
CONECT   15   14   16                                                       
CONECT   16   17   15                                                       
CONECT   17   13   16   20   31                                             
CONECT   18   13                                                            
CONECT   19   10                                                            
CONECT   20   17   22   21                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   24                                                            
CONECT   29   14                                                            
CONECT   30    9                                                            
CONECT   31   17                                                            
CONECT   32    3                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(22E)-24-Methylcholesta-5,7,22,24(24(1))-tetraen-3beta-ol	ChEBI
5,7,22,24(28)-Ergostatetraenol	ChEBI
Ergosta-5,7,22,24(24(1))-tetraen-3beta-ol	ChEBI
Ergosta-5,7,22,24(241)-tetraen-3beta-ol	ChEBI
(22E)-24-Methylcholesta-5,7,22,24(24(1))-tetraen-3b-ol	Generator
(22E)-24-Methylcholesta-5,7,22,24(24(1))-tetraen-3β-ol	Generator
Ergosta-5,7,22,24(24(1))-tetraen-3b-ol	Generator
Ergosta-5,7,22,24(24(1))-tetraen-3β-ol	Generator
Ergosta-5,7,22,24(241)-tetraen-3b-ol	Generator
Ergosta-5,7,22,24(241)-tetraen-3β-ol	Generator
Ergosta-5,7,22,24(28)-tetraen-3b-ol	Generator
Ergosta-5,7,22,24(28)-tetraen-3β-ol	Generator

Chemical Formula

C₂₈H₄₂O

Average Mass

394.6325 Da

Monoisotopic Mass

394.32357 Da

IUPAC Name

(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R,3E)-6-methyl-5-methylidenehept-3-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol

Traditional Name

5,7,22,24(28)-ergostatetraenol

CAS Registry Number

Not Available

SMILES

CC(C)C(=C)\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C

InChI Identifier

InChI=1S/C28H42O/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/h7-10,18,20,22,24-26,29H,3,11-17H2,1-2,4-6H3/b8-7+/t20-,22+,24-,25+,26+,27+,28-/m1/s1

InChI Key

SQFQJKZSFOZDJY-CVGLIYDESA-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

Species Name	Source	Reference
Aspergillus oryzae	Fungi	KNApSAcK
Candida albicans	Fungi	KNApSAcK
Candida utilis	Fungi	KNApSAcK
Cyanidium caldarium	LOTUS Database	35616633
Fusarium fujikuroi	Fungi	KNApSAcK
Saccharomyces cerevisiae	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
3-hydroxy-delta-5-steroid
3-hydroxy-delta-7-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
Delta-7-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-sterol (CHEBI:18249 )
Ergosterols and C24-methyl derivatives (LMST01031015 )

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	7.48	ALOGPS
logP	6.28	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	18.27	ChemAxon
pKa (Strongest Basic)	-1.4	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	126.91 m³·mol⁻¹	ChemAxon
Polarizability	50.41 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

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

11090531

PDB ID

Not Available

ChEBI ID

18249

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ergosta-5,7,22,24(28)-tetraen-3beta-ol (NP0066359)

MOL for NP0066359 (Ergosta-5,7,22,24(28)-tetraen-3beta-ol)

3D MOL for NP0066359 (Ergosta-5,7,22,24(28)-tetraen-3beta-ol)

3D SDF for NP0066359 (Ergosta-5,7,22,24(28)-tetraen-3beta-ol)

3D-SDF for NP0066359 (Ergosta-5,7,22,24(28)-tetraen-3beta-ol)

PDB for NP0066359 (Ergosta-5,7,22,24(28)-tetraen-3beta-ol)

3D PDB for NP0066359 (Ergosta-5,7,22,24(28)-tetraen-3beta-ol)

SMILES for NP0066359 (Ergosta-5,7,22,24(28)-tetraen-3beta-ol)

INCHI for NP0066359 (Ergosta-5,7,22,24(28)-tetraen-3beta-ol)

Structure for NP0066359 (Ergosta-5,7,22,24(28)-tetraen-3beta-ol)

3D Structure for NP0066359 (Ergosta-5,7,22,24(28)-tetraen-3beta-ol)