NP-MRD: Showing NP-Card for shidasterone (NP0172057)

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Record Information

Version

2.0

Created at

2022-09-03 08:50:44 UTC

Updated at

2022-09-03 08:50:45 UTC

NP-MRD ID

NP0172057

Secondary Accession Numbers

None

Natural Product Identification

Common Name

shidasterone

Description

Shidasterone belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, shidasterone is considered to be a sterol. shidasterone is found in Vitex canescens. shidasterone was first documented in 2004 (PMID: 15189602). Based on a literature review a small amount of articles have been published on shidasterone (PMID: 22645442) (PMID: 23150078) (PMID: 21922904) (PMID: 17698156).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309032210502D          

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M  END
> <DATABASE_ID>
NP0172057

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@](O)(C1CCC(C)(C)O1)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O6/c1-23(2)9-8-22(33-23)26(5,31)21-7-11-27(32)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-32H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22?,24+,25+,26+,27+/m0/s1

> <INCHI_KEY>
JWXMXJQGIRXWDG-SASGHFKCSA-N

> <FORMULA>
C27H42O6

> <MOLECULAR_WEIGHT>
462.627

> <EXACT_MASS>
462.298139072

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.34047011972514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,5R,7R,11S,14S,15R)-14-[(1R)-1-(5,5-dimethyloxolan-2-yl)-1-hydroxyethyl]-4,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
1.7715657770000006

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.822587617847361

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.34480134531946

> <JCHEM_PKA_STRONGEST_BASIC>
-3.153288443303487

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
125.36569999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,5R,7R,11S,14S,15R)-14-[(1R)-1-(5,5-dimethyloxolan-2-yl)-1-hydroxyethyl]-4,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       1.923 -10.533   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.990  -9.422   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.983 -10.600   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.775  -8.477   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.298  -7.029   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.837  -7.079   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.998  -6.808   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.566  -4.918   0.000  0.00  0.00           O+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  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.265  -8.558   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   33                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   31                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   31                                             
CONECT   14   13                                                            
CONECT   15   13   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   19   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   15   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   10   13   32                                             
CONECT   32   31                                                            
CONECT   33    6    2                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
22,25-Oxido-5beta-cholest-7-en-6-one-2beta,3beta,14alpha,20-tetrol	ChEBI
22,25-Oxido-5b-cholest-7-en-6-one-2b,3b,14a,20-tetrol	Generator
22,25-Oxido-5β-cholest-7-en-6-one-2β,3β,14α,20-tetrol	Generator
22,25-Oxido-5 beta-cholest-7-en-6-one-2 beta,3 beta,14 alpha,20-tetrol	MeSH

Chemical Formula

C₂₇H₄₂O₆

Average Mass

462.6270 Da

Monoisotopic Mass

462.29814 Da

IUPAC Name

(1R,2R,4S,5R,7R,11S,14S,15R)-14-[(1R)-1-(5,5-dimethyloxolan-2-yl)-1-hydroxyethyl]-4,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

Traditional Name

(1R,2R,4S,5R,7R,11S,14S,15R)-14-[(1R)-1-(5,5-dimethyloxolan-2-yl)-1-hydroxyethyl]-4,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

CAS Registry Number

Not Available

SMILES

C[C@](O)(C1CCC(C)(C)O1)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C27H42O6/c1-23(2)9-8-22(33-23)26(5,31)21-7-11-27(32)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-32H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22?,24+,25+,26+,27+/m0/s1

InChI Key

JWXMXJQGIRXWDG-SASGHFKCSA-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
Vitex canescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
Ecdysteroid
20-hydroxysteroid
3-hydroxy-delta-7-steroid
3-hydroxysteroid
2-hydroxysteroid
14-hydroxysteroid
6-oxosteroid
3-beta-hydroxysteroid
Hydroxysteroid
Oxosteroid
Delta-7-steroid
Cyclohexenone
Tertiary alcohol
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
Organoheterocyclic compound
Dialkyl ether
Ether
Oxacycle
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:26661 )
20-hydroxy steroid (CHEBI:26661 )
6-oxo steroid (CHEBI:26661 )
2beta-hydroxy steroid (CHEBI:26661 )
14alpha-hydroxy steroid (CHEBI:26661 )
phytoecdysteroid (CHEBI:26661 )
Cholesterol and derivatives (LMST01010193 )

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	2.03	ALOGPS
logP	1.77	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	13.34	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	125.37 m³·mol⁻¹	ChemAxon
Polarizability	52.34 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

20056508

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15227299

PDB ID

Not Available

ChEBI ID

26661

Good Scents ID

Not Available

References

General References

Vanyolos A, Beni Z, Dekany M, Simon A, Bathori M: Novel ecdysteroids from Serratula wolffii. ScientificWorldJournal. 2012;2012:651275. doi: 10.1100/2012/651275. Epub 2012 May 2. [PubMed:22645442 ]
Ochieng CO, Ishola IO, Opiyo SA, Manguro LA, Owuor PO, Wong KC: Phytoecdysteroids from the stem bark of Vitex doniana and their anti-inflammatory effects. Planta Med. 2013 Jan;79(1):52-9. doi: 10.1055/s-0032-1327880. Epub 2012 Nov 13. [PubMed:23150078 ]
Hincapie CA, Monsalve Z, Parada K, Lamilla C, Alarcon J, Cespedes CL, Seigler D: Insect growth regulatory activity of Blechnum chilense. Nat Prod Commun. 2011 Aug;6(8):1085-8. [PubMed:21922904 ]
Simon A, Toth G, Liktor-Busa E, Kele Z, Takacs M, Gergely A, Bathori M: Three new steroids from the roots of Serratula wolffii. Steroids. 2007 Oct;72(11-12):751-5. doi: 10.1016/j.steroids.2007.06.004. Epub 2007 Jul 6. [PubMed:17698156 ]
Bathori M, Pongracz Z, Omacht R, Mathe I: Preparative scale purification of shidasterone, 2-deoxy-polypodine b and 9a,20-dihydroxyecdysone from Silene italica ssp. nemoralis. J Chromatogr Sci. 2004 May-Jun;42(5):275-9. doi: 10.1093/chromsci/42.5.275. [PubMed:15189602 ]
LOTUS database [Link]

Showing NP-Card for shidasterone (NP0172057)

MOL for NP0172057 (shidasterone)

3D MOL for NP0172057 (shidasterone)

3D SDF for NP0172057 (shidasterone)

3D-SDF for NP0172057 (shidasterone)

PDB for NP0172057 (shidasterone)

3D PDB for NP0172057 (shidasterone)

SMILES for NP0172057 (shidasterone)

INCHI for NP0172057 (shidasterone)

Structure for NP0172057 (shidasterone)

3D Structure for NP0172057 (shidasterone)