NP-MRD: Showing NP-Card for 5α-ergosta-7,22-dien-3β-ol (NP0256638)

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Record Information

Version

2.0

Created at

2022-09-07 21:31:58 UTC

Updated at

2022-09-07 21:31:58 UTC

NP-MRD ID

NP0256638

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5α-ergosta-7,22-dien-3β-ol

Description

5Alpha-ergosta-7,22-dien-3beta-ol, also known as 5-dihydroergosterol, 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, 5alpha-ergosta-7,22-dien-3beta-ol is considered to be a sterol. 5α-ergosta-7,22-dien-3β-ol is found in Acanthaster planci, Alstroemeria aurea, Astraeus hygrometricus, Axinella cannabina, Clerodendrum fragrans, Conium maculatum, Cucumis sativus, Epichloe festucae, Eutypa lata, Fomitopsis officinalis, Fomitopsis pinicola, Galdieria sulphuraria, Ganoderma annulare, Ganoderma applanatum, Ganoderma australe, Ganoderma carnosum, Ganoderma pfeifferi, Ganoderma sinense, Ganoderma tsugae, Hypholoma fasciculare, Inonotus obliquus, Lentinula edodes, Leptosphaeria maculans, Ligularia nanchuanica, Mikania micrantha, Morchella esculenta, Petrosia ficiformis, Phallusia nigra, Polyporus umbellatus, Rhizophora apiculata, Sarcodon scabrosus, Trametes versicolor, Tylopilus neofelleus, Tylopilus plumbeoviolaceus and Viburnum cylindricum. 5α-ergosta-7,22-dien-3β-ol was first documented in 2003 (PMID: 12781809). Based on a literature review a small amount of articles have been published on 5alpha-ergosta-7,22-dien-3beta-ol (PMID: 34591394) (PMID: 26382563) (PMID: 24740357).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072223312D          

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M  END

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  Mrv1652309072223312D          

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M  END
> <DATABASE_ID>
NP0256638

> <DATABASE_NAME>
NP-MRD

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

> <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+/t19-,20+,21-,22-,24+,25-,26-,27-,28+/m0/s1

> <INCHI_KEY>
QOXPZVASXWSKKU-UEIWAABPSA-N

> <FORMULA>
C28H46O

> <MOLECULAR_WEIGHT>
398.675

> <EXACT_MASS>
398.354866101

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.67016073707687

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
7.037986470333335

> <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

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.955  -2.378   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.571  -2.589   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.516  -1.373   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.206  -5.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.676  -4.226   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   28                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   14   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   13   10   29                                             
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
5-Dihydroergosterol	ChEBI
5a-Ergosta-7,22-dien-3b-ol	Generator
5Α-ergosta-7,22-dien-3β-ol	Generator

Chemical Formula

C₂₈H₄₆O

Average Mass

398.6750 Da

Monoisotopic Mass

398.35487 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

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+/t19-,20+,21-,22-,24+,25-,26-,27-,28+/m0/s1

InChI Key

QOXPZVASXWSKKU-UEIWAABPSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Acanthaster planci	LOTUS Database	35616633
Alstroemeria aurantiaca	LOTUS Database	35616633
Astraeus hygrometricus	LOTUS Database	35616633
Axinella cannabina	LOTUS Database	35616633
Clerodendrum fragrans	LOTUS Database	35616633
Conium maculatum	LOTUS Database	35616633
Cucumis sativus	LOTUS Database	35616633
Epichloe festucae	LOTUS Database	35616633
Eutypa lata	LOTUS Database	35616633
Fomitopsis officinalis	LOTUS Database	35616633
Fomitopsis pinicola	LOTUS Database	35616633
Galdieria sulphuraria	LOTUS Database	35616633
Ganoderma annulare	LOTUS Database	35616633
Ganoderma applanatum	LOTUS Database	35616633
Ganoderma australe	LOTUS Database	35616633
Ganoderma carnosum	LOTUS Database	35616633
Ganoderma pfeifferi	LOTUS Database	35616633
Ganoderma sinense	LOTUS Database	35616633
Ganoderma tsugae	LOTUS Database	35616633
Hypholoma fasciculare	LOTUS Database	35616633
Inonotus obliquus	LOTUS Database	35616633
Lentinus edodes	LOTUS Database	35616633
Leptosphaeria maculans	LOTUS Database	35616633
Ligularia nanchuanica	LOTUS Database	35616633
Mikania micrantha	LOTUS Database	35616633
Morchella esculenta	LOTUS Database	35616633
Petrosia ficiformis	LOTUS Database	35616633
Phallusia nigra	LOTUS Database	35616633
Polyporus umbellatus	LOTUS Database	35616633
Rhizophora apiculata	LOTUS Database	35616633
Sarcodon scabrosus	LOTUS Database	35616633
Trametes Versicolor	LOTUS Database	35616633
Tylopilus neofelleus	LOTUS Database	35616633
Tylopilus plumbeoviolaceus	LOTUS Database	35616633
Viburnum cylindricum	LOTUS Database	35616633

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-beta-hydroxysteroid
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

3beta-sterol (CHEBI:20651 )
Ergosterols and C24-methyl derivatives (LMST01030094 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00035913

Chemspider ID

4446722

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283628

PDB ID

Not Available

ChEBI ID

20651

Good Scents ID

Not Available

References

General References

Lagunes-Castro MS, Aguila S, Herrera-Covarrubias D, Hernandez-Aguilar ME, Trigos A, Vidal-Limon A, Suarez-Medellin J: Structure-Based Virtual Screening of Sterols and Triterpenoids Isolated from Ganoderma (Agaricomycetes) Medicinal Mushrooms Shows Differences in Their Affinity for Human Glucocorticoid and Mineralocorticoid Receptors. Int J Med Mushrooms. 2021;23(9):1-13. doi: 10.1615/IntJMedMushrooms.2021039290. [PubMed:34591394 ]
Gao J, Wang LW, Zheng HC, Damirin A, Ma CM: Cytotoxic constituents of Lasiosphaera fenzlii on different cell lines and the synergistic effects with paclitaxel. Nat Prod Res. 2016 Aug;30(16):1862-5. doi: 10.1080/14786419.2015.1075526. Epub 2015 Sep 18. [PubMed:26382563 ]
Rani MP, Raghu KG, Nair MS, Padmakumari KP: Isolation and identification of alpha-glucosidase and protein glycation inhibitors from Stereospermum colais. Appl Biochem Biotechnol. 2014 Jun;173(4):946-56. doi: 10.1007/s12010-014-0898-y. Epub 2014 Apr 17. [PubMed:24740357 ]
Smania EF, Delle Monache F, Smania A Jr, Yunes RA, Cuneo RS: Antifungal activity of sterols and triterpenes isolated from Ganoderma annulare. Fitoterapia. 2003 Jun;74(4):375-7. doi: 10.1016/s0367-326x(03)00064-9. [PubMed:12781809 ]
LOTUS database [Link]

Showing NP-Card for 5α-ergosta-7,22-dien-3β-ol (NP0256638)

MOL for NP0256638 (5α-ergosta-7,22-dien-3β-ol)

3D MOL for NP0256638 (5α-ergosta-7,22-dien-3β-ol)

3D SDF for NP0256638 (5α-ergosta-7,22-dien-3β-ol)

3D-SDF for NP0256638 (5α-ergosta-7,22-dien-3β-ol)

PDB for NP0256638 (5α-ergosta-7,22-dien-3β-ol)

3D PDB for NP0256638 (5α-ergosta-7,22-dien-3β-ol)

SMILES for NP0256638 (5α-ergosta-7,22-dien-3β-ol)

INCHI for NP0256638 (5α-ergosta-7,22-dien-3β-ol)

Structure for NP0256638 (5α-ergosta-7,22-dien-3β-ol)

3D Structure for NP0256638 (5α-ergosta-7,22-dien-3β-ol)