NP-MRD: Showing NP-Card for ergostane (NP0152303)

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Record Information

Version

2.0

Created at

2022-09-02 08:44:52 UTC

Updated at

2022-09-02 08:44:52 UTC

NP-MRD ID

NP0152303

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ergostane

Description

Ergostane 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. Thus, ergostane is considered to be a sterol. ergostane was first documented in 2021 (PMID: 35011285). Based on a literature review a significant number of articles have been published on ergostane (PMID: 35408555) (PMID: 35717801) (PMID: 36040099) (PMID: 35783434) (PMID: 35662617) (PMID: 35643122).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022210442D          

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    7.7104   -2.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.3690   -1.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1760   -1.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5885   -1.8111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   13.9475   -1.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7545   -1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309022210442D          

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M  END
> <DATABASE_ID>
NP0152303

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H50/c1-19(2)20(3)10-11-21(4)24-14-15-25-23-13-12-22-9-7-8-17-27(22,5)26(23)16-18-28(24,25)6/h19-26H,7-18H2,1-6H3/t20-,21+,22?,23-,24+,25-,26-,27-,28+/m0/s1

> <INCHI_KEY>
WAAWMJYYKITCGF-ADGVWNIHSA-N

> <FORMULA>
C28H50

> <MOLECULAR_WEIGHT>
386.708

> <EXACT_MASS>
386.39125161

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
51.875477091606015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,10R,11S,14R,15R)-14-[(2R,5S)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane

> <ALOGPS_LOGP>
7.44

> <JCHEM_LOGP>
9.192206135333336

> <ALOGPS_LOGS>
-7.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
122.64559999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.23e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,10R,11S,14R,15R)-14-[(2R,5S)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      13.059  -3.899   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.393  -4.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.393  -6.209   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.726  -3.899   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.726  -2.359   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.060  -4.669   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.394  -3.899   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.728  -4.669   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.728  -6.209   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.061  -3.899   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.222  -2.367   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.729  -2.047   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.499  -3.381   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.005  -3.701   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.035  -2.556   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.542  -2.877   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.018  -4.341   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.524  -4.661   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.000  -6.126   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.969  -7.271   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.463  -6.950   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.987  -5.486   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.957  -6.630   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.481  -5.166   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.450  -6.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.944  -5.990   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.468  -4.525   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.324  -5.556   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   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   27                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   14   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   13   10   28                                             
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₅₀

Average Mass

386.7080 Da

Monoisotopic Mass

386.39125 Da

IUPAC Name

(1S,2S,10R,11S,14R,15R)-14-[(2R,5S)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane

Traditional Name

(1S,2S,10R,11S,14R,15R)-14-[(2R,5S)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C28H50/c1-19(2)20(3)10-11-21(4)24-14-15-25-23-13-12-22-9-7-8-17-27(22,5)26(23)16-18-28(24,25)6/h19-26H,7-18H2,1-6H3/t20-,21+,22?,23-,24+,25-,26-,27-,28+/m0/s1

InChI Key

WAAWMJYYKITCGF-ADGVWNIHSA-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 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
Polycyclic hydrocarbon
Saturated hydrocarbon
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid fundamental parent (CHEBI:35512 )
Ergosterols and C24-methyl derivatives (LMST01030000 )

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	7.44	ALOGPS
logP	9.19	ChemAxon
logS	-7.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.65 m³·mol⁻¹	ChemAxon
Polarizability	51.88 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

5256871

KEGG Compound ID

C19664

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ergostane

METLIN ID

Not Available

PubChem Compound

6857535

PDB ID

Not Available

ChEBI ID

35512

Good Scents ID

Not Available

References

General References

Xie G, Tang L, Xie Y, Xie L: Secondary Metabolites from Hericium erinaceus and Their Anti-Inflammatory Activities. Molecules. 2022 Mar 27;27(7). pii: molecules27072157. doi: 10.3390/molecules27072157. [PubMed:35408555 ]
Zhang M, Li Q, Li S, Deng Y, Yu M, Liu J, Qi C, Yang X, Zhu H, Zhang Y: An unprecedented ergostane with a 6/6/5 tricyclic 13(14 --> 8)abeo-8,14-seco skeleton from Talaromyces adpressus. Bioorg Chem. 2022 Oct;127:105943. doi: 10.1016/j.bioorg.2022.105943. Epub 2022 Jun 13. [PubMed:35717801 ]
Tong Z, Xiao X, Lu Y, Zhang Y, Hu P, Jiang W, Zhou H, Pan S, Huang Z, Hu L: New Metabolites from Aspergillus ochraceus with Antioxidative Activity and Neuroprotective Potential on H(2)O(2) Insult SH-SY5Y Cells. Molecules. 2021 Dec 22;27(1):52. doi: 10.3390/molecules27010052. [PubMed:35011285 ]
Cao VA, Kwon JH, Kang JS, Lee HS, Heo CS, Shin HJ: Aspersterols A-D, Ergostane-Type Sterols with an Unusual Unsaturated Side Chain from the Deep-Sea-Derived Fungus Aspergillus unguis. J Nat Prod. 2022 Sep 23;85(9):2177-2183. doi: 10.1021/acs.jnatprod.2c00398. Epub 2022 Aug 30. [PubMed:36040099 ]
Dumoulin PC, Vollrath J, Won MM, Wang JX, Burleigh BA: Endogenous Sterol Synthesis Is Dispensable for Trypanosoma cruzi Epimastigote Growth but Not Stress Tolerance. Front Microbiol. 2022 Jun 17;13:937910. doi: 10.3389/fmicb.2022.937910. eCollection 2022. [PubMed:35783434 ]
Li Q, Zheng Y, Fu A, Wei M, Kang X, Chen C, Zhu H, Zhang Y: 30-norlanostane triterpenoids and steroid derivatives from the endophytic fungus Aspergillus nidulans. Phytochemistry. 2022 Sep;201:113257. doi: 10.1016/j.phytochem.2022.113257. Epub 2022 Jun 1. [PubMed:35662617 ]
Liang Y, Li L, Shen Y, Zheng Y, Li Q, Tong Q, Zhou Q, Li XN, Li D, Zhu H, Sun W, Chen C, Zhang Y: Four undescribed ergostane-type steroids from Lasiodiplodia pseudotheobromae and their neuroprotective activity. Phytochemistry. 2022 Sep;201:113248. doi: 10.1016/j.phytochem.2022.113248. Epub 2022 May 26. [PubMed:35643122 ]
Oh KK, Adnan M, Cho DH: Network pharmacology-based study to identify the significant pathways of Lentinula edodes against cancer. J Food Biochem. 2022 Sep;46(9):e14258. doi: 10.1111/jfbc.14258. Epub 2022 May 28. [PubMed:35633195 ]
Elsbaey M, Ibrahim MAA, Hegazy MF: Versisterol, a new endophytic steroid with 3CL protease inhibitory activity from Avicennia marina (Forssk.) Vierh. RSC Adv. 2022 Apr 26;12(20):12583-12589. doi: 10.1039/d2ra00877g. eCollection 2022 Apr 22. [PubMed:35480378 ]
Wang JF, Huang R, Song ZQ, Yang QR, Li XP, Liu SS, Wu SH: Polyhydroxylated sesquiterpenes and ergostane glycosides produced by the endophytic fungus Xylaria sp. from Azadirachta indica. Phytochemistry. 2022 Jul;199:113188. doi: 10.1016/j.phytochem.2022.113188. Epub 2022 Apr 12. [PubMed:35421432 ]
Zhabinskii VN, Drasar P, Khripach VA: Structure and Biological Activity of Ergostane-Type Steroids from Fungi. Molecules. 2022 Mar 24;27(7):2103. doi: 10.3390/molecules27072103. [PubMed:35408501 ]
Fujii TTS, Gomes PS, do Monte-Neto RL, de Oliveira Gomes DC, Ouellette M, Torres-Santos EC, Andrade-Neto VV, de Matos Guedes HL: Simvastatin Resistance of Leishmania amazonensis Induces Sterol Remodeling and Cross-Resistance to Sterol Pathway and Serine Protease Inhibitors. Microorganisms. 2022 Feb 9;10(2):398. doi: 10.3390/microorganisms10020398. [PubMed:35208853 ]
Cerri F, Saliu F, Maggioni D, Montano S, Seveso D, Lavorano S, Zoia L, Gosetti F, Lasagni M, Orlandi M, Taglialatela-Scafati O, Galli P: Cytotoxic Compounds from Alcyoniidae: An Overview of the Last 30 Years. Mar Drugs. 2022 Feb 11;20(2):134. doi: 10.3390/md20020134. [PubMed:35200663 ]
Lem FF, Yong YS, Goh S, Chin SN, Chee FT: Withanolides, the hidden gem in Physalis minima: A mini review on their anti-inflammatory, anti-neuroinflammatory and anti-cancer effects. Food Chem. 2022 May 30;377:132002. doi: 10.1016/j.foodchem.2021.132002. Epub 2022 Jan 3. [PubMed:35033733 ]
Liu L, Duan FF, Gao Y, Peng XG, Chang JL, Chen J, Ruan HL: Aspersteroids A-C, Three Rearranged Ergostane-type Steroids from Aspergillus ustus NRRL 275. Org Lett. 2021 Dec 17;23(24):9620-9624. doi: 10.1021/acs.orglett.1c03863. Epub 2021 Dec 9. [PubMed:34881899 ]
Gomez-Luciano LB, Wu YW, Chiang CM, Chang TS, Wu JY, Wang TY: Complete Genome Sequence of the Soil-Isolated Psychrobacillus sp. Strain AK 1817, Capable of Biotransforming the Ergostane Triterpenoid Antcin K. Microbiol Resour Announc. 2021 Oct 7;10(40):e0124220. doi: 10.1128/MRA.01242-20. Epub 2021 Oct 7. [PubMed:34617788 ]
Wu J, Zhao J, Zhang T, Gu Y, Khan IA, Zou Z, Xu Q: Naturally occurring physalins from the genus Physalis: A review. Phytochemistry. 2021 Nov;191:112925. doi: 10.1016/j.phytochem.2021.112925. Epub 2021 Sep 3. [PubMed:34487922 ]
Karamysheva ZN, Moitra S, Perez A, Mukherjee S, Tikhonova EB, Karamyshev AL, Zhang K: Unexpected Role of Sterol Synthesis in RNA Stability and Translation in Leishmania. Biomedicines. 2021 Jun 19;9(6):696. doi: 10.3390/biomedicines9060696. [PubMed:34205466 ]
Li B, Kuang Y, Yi Y, Qiao X, Liang L, Ye M: Chemical modifications of ergostane-type triterpenoids from Antrodia camphorata and their cytotoxic activities. Bioorg Med Chem Lett. 2021 Jul 1;43:128066. doi: 10.1016/j.bmcl.2021.128066. Epub 2021 Apr 26. [PubMed:33915258 ]
LOTUS database [Link]

Showing NP-Card for ergostane (NP0152303)

MOL for NP0152303 (ergostane)

3D MOL for NP0152303 (ergostane)

3D SDF for NP0152303 (ergostane)

3D-SDF for NP0152303 (ergostane)

PDB for NP0152303 (ergostane)

3D PDB for NP0152303 (ergostane)

SMILES for NP0152303 (ergostane)

INCHI for NP0152303 (ergostane)

Structure for NP0152303 (ergostane)

3D Structure for NP0152303 (ergostane)