NP-MRD: Showing NP-Card for Ergosta-7,22-dien-3-one (NP0140753)

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Record Information

Version

2.0

Created at

2022-06-29 21:50:14 UTC

Updated at

2022-06-29 21:50:14 UTC

NP-MRD ID

NP0140753

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ergosta-7,22-dien-3-one

Description

Ergosta-7,22-dien-3-one 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. Ergosta-7,22-dien-3-one was first documented in 2017 (PMID: 28605335). Based on a literature review a small amount of articles have been published on Ergosta-7,22-dien-3-one (PMID: 34591394) (PMID: 34121543) (PMID: 32375510).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292223502D          

 29 32  0  0  1  0            999 V2000
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    8.7583   -1.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6302   -2.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306292223502D          

 29 32  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0140753

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H](C)C=C[C@@H](C)[C@H]1CC[C@H]2C3=CCC4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O/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/h7-8,10,18-21,24-26H,9,11-17H2,1-6H3/t19-,20+,21?,24+,25-,26-,27-,28+/m0/s1

> <INCHI_KEY>
AHWOEMBXZXGDBQ-AQGSFBQWSA-N

> <FORMULA>
C28H44O

> <MOLECULAR_WEIGHT>
396.659

> <EXACT_MASS>
396.339216037

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
50.531620266818386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.86

> <JCHEM_LOGP>
7.245487272

> <ALOGPS_LOGS>
-6.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.353012991872513

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
125.25359999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.32e-05 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.353  -2.485   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.878  -2.275   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.458  -0.848   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.823  -3.490   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.349  -3.280   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.243  -4.917   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    2   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   10   15   29                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   17   23   28                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   21                                                       
CONECT   28   22                                                            
CONECT   29   14                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
5alpha-Ergosta-7,22-dien-3-one	MeSH

Chemical Formula

C₂₈H₄₄O

Average Mass

396.6590 Da

Monoisotopic Mass

396.33922 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H](C)C=C[C@@H](C)[C@H]1CC[C@H]2C3=CCC4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C28H44O/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/h7-8,10,18-21,24-26H,9,11-17H2,1-6H3/t19-,20+,21?,24+,25-,26-,27-,28+/m0/s1

InChI Key

AHWOEMBXZXGDBQ-AQGSFBQWSA-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

Not Available

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
Oxosteroid
3-oxosteroid
3-oxo-delta-7-steroid
Delta-7-steroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	6.86	ALOGPS
logP	7.25	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	125.25 m³·mol⁻¹	ChemAxon
Polarizability	50.53 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

C00023765

Chemspider ID

58107310

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

99511

PDB ID

Not Available

ChEBI ID

Not Available

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 ]
Zeng Q, Singh R, Ye Y, Cheng S, Fan C, Zeng Q: Calvatia Lilacina Extracts Exert Anti-Breast-Cancer Bioactivity through the Apoptosis Induction Dependent on Mitochondrial Reactive Oxygen Species and Caspase Activation. Nutr Cancer. 2022;74(3):1058-1070. doi: 10.1080/01635581.2021.1936576. Epub 2021 Jun 12. [PubMed:34121543 ]
Al-Rabia MW, Mohamed GA, Ibrahim SRM, Asfour HZ: Anti-inflammatory ergosterol derivatives from the endophytic fungus Fusarium chlamydosporum. Nat Prod Res. 2021 Dec;35(23):5011-5020. doi: 10.1080/14786419.2020.1762185. Epub 2020 May 6. [PubMed:32375510 ]
Ramos-Ligonio A, Lopez-Monteon A, Lagunes-Castro MS, Suarez-Medellin J, Espinoza C, Mendoza G, Trigos A: In Vitro Expression of Toll-Like Receptors and Proinflammatory Molecules Induced by Ergosta- 7,22-Dien-3-One Isolated from a Wild Mexican Strain of Ganoderma oerstedii (Agaricomycetes). Int J Med Mushrooms. 2017;19(3):203-211. doi: 10.1615/IntJMedMushrooms.v19.i3.20. [PubMed:28605335 ]

Showing NP-Card for Ergosta-7,22-dien-3-one (NP0140753)

MOL for NP0140753 (Ergosta-7,22-dien-3-one)

3D MOL for NP0140753 (Ergosta-7,22-dien-3-one)

3D SDF for NP0140753 (Ergosta-7,22-dien-3-one)

3D-SDF for NP0140753 (Ergosta-7,22-dien-3-one)

PDB for NP0140753 (Ergosta-7,22-dien-3-one)

3D PDB for NP0140753 (Ergosta-7,22-dien-3-one)

SMILES for NP0140753 (Ergosta-7,22-dien-3-one)

INCHI for NP0140753 (Ergosta-7,22-dien-3-one)

Structure for NP0140753 (Ergosta-7,22-dien-3-one)

3D Structure for NP0140753 (Ergosta-7,22-dien-3-one)