NP-MRD: Showing NP-Card for 5,20,26-Trihydroxyecdysone 20,22-acetonide (NP0076065)

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Record Information

Version

2.0

Created at

2022-04-28 21:14:44 UTC

Updated at

2022-04-28 21:14:45 UTC

NP-MRD ID

NP0076065

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,20,26-Trihydroxyecdysone 20,22-acetonide

Description

(1R,2R,4S,5R,7S,11S,14S,15R)-14-[(4R,5R)-5-[(3S)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-4,5,7,11-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-8-one belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. 5,20,26-Trihydroxyecdysone 20,22-acetonide is found in Silene viridiflora. Based on a literature review very few articles have been published on (1R,2R,4S,5R,7S,11S,14S,15R)-14-[(4R,5R)-5-[(3S)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-4,5,7,11-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-8-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223142D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282223142D          

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    0.0962    0.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    2.7283    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2236    3.4707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0408    3.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1861    2.5457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586    2.1567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3457    1.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9970    0.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8842    0.0158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7713   -0.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4227   -1.3078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7014   -0.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0669    0.1287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2469    4.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8309    3.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1630    3.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073    2.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    0.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    2.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4641    0.1163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7793    2.7844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 16 19  1  6  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  1  0  0  0
 26 30  1  1  0  0  0
 21 31  1  0  0  0  0
 21 32  1  0  0  0  0
 19 33  1  1  0  0  0
 13 34  1  6  0  0  0
 12 35  1  1  0  0  0
  5 36  1  6  0  0  0
  4 37  1  6  0  0  0
  2 38  1  6  0  0  0
  1 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0076065

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O9/c1-24(2)38-23(9-10-25(3,35)16-31)28(6,39-24)21-8-12-29(36)18-13-22(34)30(37)15-20(33)19(32)14-27(30,5)17(18)7-11-26(21,29)4/h13,17,19-21,23,31-33,35-37H,7-12,14-16H2,1-6H3/t17-,19-,20+,21-,23+,25-,26+,27+,28+,29+,30+/m0/s1

> <INCHI_KEY>
ZJNBRMJTFYQDIR-REYDSHAQSA-N

> <FORMULA>
C30H48O9

> <MOLECULAR_WEIGHT>
552.705

> <EXACT_MASS>
552.329833126

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
61.07502259370368

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,5R,7S,11S,14S,15R)-14-[(4R,5R)-5-[(3S)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-4,5,7,11-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
0.4451577246666643

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.452274945195342

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.514742516978753

> <JCHEM_PKA_STRONGEST_BASIC>
-3.067804031649163

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
143.98290000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,5R,7S,11S,14S,15R)-14-[(4R,5R)-5-[(3S)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-4,5,7,11-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.943   1.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.474  -0.960   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.179   1.534   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.284   6.479   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.810   6.268   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.081   4.752   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.723   4.026   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.512   2.500   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.728   1.555   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.517   0.030   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.306  -1.496   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.522  -2.441   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.043  -0.181   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.992   0.240   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.194   7.759   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.284   6.711   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.304   5.906   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.200   5.313   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.764   0.984   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.897   4.562   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       6.466   0.217   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       9.968   2.301   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       8.921   5.197   0.000  0.00  0.00           O+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10   37                                             
CONECT    5    4    6    7   36                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   18   35                                             
CONECT   13   12   14   16   34                                             
CONECT   14   13   15                                                       
CONECT   15   14    7                                                       
CONECT   16   13   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   12                                                       
CONECT   19   16   20   23   33                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   31   32                                             
CONECT   22   21   23                                                       
CONECT   23   22   19   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   29   30                                             
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26                                                            
CONECT   30   26                                                            
CONECT   31   21                                                            
CONECT   32   21                                                            
CONECT   33   19                                                            
CONECT   34   13                                                            
CONECT   35   12                                                            
CONECT   36    5                                                            
CONECT   37    4                                                            
CONECT   38    2                                                            
CONECT   39    1                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₉

Average Mass

552.7050 Da

Monoisotopic Mass

552.32983 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H48O9/c1-24(2)38-23(9-10-25(3,35)16-31)28(6,39-24)21-8-12-29(36)18-13-22(34)30(37)15-20(33)19(32)14-27(30,5)17(18)7-11-26(21,29)4/h13,17,19-21,23,31-33,35-37H,7-12,14-16H2,1-6H3/t17-,19-,20+,21-,23+,25-,26+,27+,28+,29+,30+/m0/s1

InChI Key

ZJNBRMJTFYQDIR-REYDSHAQSA-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
Silene viridiflora	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Tetrahydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Tetrahydroxy bile acid, alcohol, or derivatives
6-oxosteroid
3-beta-hydroxysteroid
Oxosteroid
Hydroxysteroid
5-hydroxysteroid
14-hydroxysteroid
2-hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Delta-7-steroid
Ketal
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Meta-dioxolane
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	1.34	ALOGPS
logP	0.45	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.51	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	143.98 m³·mol⁻¹	ChemAxon
Polarizability	61.08 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

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

163044241

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 5,20,26-Trihydroxyecdysone 20,22-acetonide (NP0076065)

MOL for NP0076065 (5,20,26-Trihydroxyecdysone 20,22-acetonide)

3D MOL for NP0076065 (5,20,26-Trihydroxyecdysone 20,22-acetonide)

3D SDF for NP0076065 (5,20,26-Trihydroxyecdysone 20,22-acetonide)

3D-SDF for NP0076065 (5,20,26-Trihydroxyecdysone 20,22-acetonide)

PDB for NP0076065 (5,20,26-Trihydroxyecdysone 20,22-acetonide)

3D PDB for NP0076065 (5,20,26-Trihydroxyecdysone 20,22-acetonide)

SMILES for NP0076065 (5,20,26-Trihydroxyecdysone 20,22-acetonide)

INCHI for NP0076065 (5,20,26-Trihydroxyecdysone 20,22-acetonide)

Structure for NP0076065 (5,20,26-Trihydroxyecdysone 20,22-acetonide)

3D Structure for NP0076065 (5,20,26-Trihydroxyecdysone 20,22-acetonide)