NP-MRD: Showing NP-Card for 20,26-dihydroxyecdysone (NP0181617)

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Record Information

Version

2.0

Created at

2022-09-03 20:09:57 UTC

Updated at

2022-09-03 20:09:57 UTC

NP-MRD ID

NP0181617

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20,26-dihydroxyecdysone

Description

20,26-Dihydroxyecdysone belongs to the class of organic compounds known as hydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing at least hydroxyl group. Thus, 20,26-dihydroxyecdysone is considered to be a sterol lipid molecule. 20,26-dihydroxyecdysone is found in Cyanotis arachnoidea. 20,26-Dihydroxyecdysone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv1652301251922052D          

 37 40  0  0  1  0            999 V2000
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M  END

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  Mrv1652301251922052D          

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   24.5544  -22.3042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   31.7692  -17.9285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2752  -21.0108    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  6  0  0  0
  2  6  1  0  0  0  0
  2  7  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  1  0  0  0
  4 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  1  0  0  0  0
  8 15  1  1  0  0  0
 12 16  1  0  0  0  0
 12 17  1  0  0  0  0
 12 18  1  1  0  0  0
 14 19  2  0  0  0  0
 15 20  1  0  0  0  0
 15 21  1  6  0  0  0
 15 22  1  0  0  0  0
 16 23  1  0  0  0  0
 17 24  1  0  0  0  0
 20 25  1  0  0  0  0
 20 26  1  6  0  0  0
 23 27  1  0  0  0  0
 24 28  1  1  0  0  0
 25 29  1  0  0  0  0
 27 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
  8 11  1  0  0  0  0
  9 13  1  0  0  0  0
 14 16  1  0  0  0  0
 24 27  1  0  0  0  0
 16 35  1  1  0  0  0
 32 36  1  0  0  0  0
  6 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0181617

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC[C@]3(C)[C@H](CC[C@@]3(O)C1=CC(=O)[C@]1([H])C[C@@H](O)[C@@H](O)C[C@]21C)[C@@](C)(O)[C@H](O)CCC(C)(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O8/c1-23(33,14-28)8-7-22(32)26(4,34)21-6-10-27(35)16-11-18(29)17-12-19(30)20(31)13-24(17,2)15(16)5-9-25(21,27)3/h11,15,17,19-22,28,30-35H,5-10,12-14H2,1-4H3/t15-,17-,19+,20-,21-,22+,23?,24+,25+,26+,27+/m0/s1

> <INCHI_KEY>
RRCGNPRHZQPOOT-FFBSXHGNSA-N

> <FORMULA>
C27H44O8

> <MOLECULAR_WEIGHT>
496.641

> <EXACT_MASS>
496.303618377

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
54.72364813188276

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3R)-2,3,6,7-tetrahydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <ALOGPS_LOGP>
0.79

> <JCHEM_LOGP>
-0.4370477619999996

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.630607894872764

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.193286361778153

> <JCHEM_PKA_STRONGEST_BASIC>
-3.067803944313658

> <JCHEM_POLAR_SURFACE_AREA>
158.68

> <JCHEM_REFRACTIVITY>
130.4195

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3R)-2,3,6,7-tetrahydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-JAN-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JAN-19         0                                  
HETATM    1  C   UNK     0      49.865 -37.642   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      48.519 -38.430   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      49.872 -36.088   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      52.563 -37.621   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      49.865 -39.077   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      47.180 -37.656   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      48.498 -39.894   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      51.217 -35.314   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      48.512 -35.321   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      49.823 -34.617   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      52.563 -36.102   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      45.856 -38.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      47.166 -36.108   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      47.194 -40.738   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      51.224 -33.801   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      45.856 -39.971   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      44.524 -37.677   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      45.852 -36.846   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      47.166 -42.167   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      52.542 -33.041   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      48.819 -32.877   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      50.911 -32.125   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      44.524 -40.745   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      43.207 -38.437   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      53.853 -33.808   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      52.471 -30.981   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      43.207 -39.971   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      41.896 -37.677   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      55.170 -33.055   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      41.896 -40.724   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      56.474 -33.815   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      57.792 -33.062   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      56.474 -35.413   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      57.856 -34.497   0.000  0.00  0.00           O+0
HETATM   35  H   UNK     0      45.835 -41.634   0.000  0.00  0.00           H+0
HETATM   36  O   UNK     0      59.302 -33.466   0.000  0.00  0.00           O+0
HETATM   37  H   UNK     0      47.180 -39.220   0.000  0.00  0.00           H+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6    7                                                  
CONECT    3    1    8    9   10                                             
CONECT    4    1   11                                                       
CONECT    5    1                                                            
CONECT    6    2   12   13   37                                             
CONECT    7    2   14                                                       
CONECT    8    3   15   11                                                  
CONECT    9    3   13                                                       
CONECT   10    3                                                            
CONECT   11    4    8                                                       
CONECT   12    6   16   17   18                                             
CONECT   13    6    9                                                       
CONECT   14    7   19   16                                                  
CONECT   15    8   20   21   22                                             
CONECT   16   12   23   14   35                                             
CONECT   17   12   24                                                       
CONECT   18   12                                                            
CONECT   19   14                                                            
CONECT   20   15   25   26                                                  
CONECT   21   15                                                            
CONECT   22   15                                                            
CONECT   23   16   27                                                       
CONECT   24   17   28   27                                                  
CONECT   25   20   29                                                       
CONECT   26   20                                                            
CONECT   27   23   30   24                                                  
CONECT   28   24                                                            
CONECT   29   25   31                                                       
CONECT   30   27                                                            
CONECT   31   29   32   33   34                                             
CONECT   32   31   36                                                       
CONECT   33   31                                                            
CONECT   34   31                                                            
CONECT   35   16                                                            
CONECT   36   32                                                            
CONECT   37    6                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₄O₈

Average Mass

496.6410 Da

Monoisotopic Mass

496.30362 Da

IUPAC Name

(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3R)-2,3,6,7-tetrahydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

Traditional Name

(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2R,3R)-2,3,6,7-tetrahydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

CAS Registry Number

Not Available

SMILES

[H][C@]12CC[C@]3(C)[C@H](CC[C@@]3(O)C1=CC(=O)[C@]1([H])C[C@@H](O)[C@@H](O)C[C@]21C)[C@@](C)(O)[C@H](O)CCC(C)(O)CO

InChI Identifier

InChI=1S/C27H44O8/c1-23(33,14-28)8-7-22(32)26(4,34)21-6-10-27(35)16-11-18(29)17-12-19(30)20(31)13-24(17,2)15(16)5-9-25(21,27)3/h11,15,17,19-22,28,30-35H,5-10,12-14H2,1-4H3/t15-,17-,19+,20-,21-,22+,23?,24+,25+,26+,27+/m0/s1

InChI Key

RRCGNPRHZQPOOT-FFBSXHGNSA-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
Cyanotis arachnoidea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing at least hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Hydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Hexahydroxy bile acid, alcohol, or derivatives
26-hydroxysteroid
Ecdysteroid
25-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
20-hydroxysteroid
3-hydroxy-delta-7-steroid
3-hydroxysteroid
2-hydroxysteroid
14-hydroxysteroid
6-oxosteroid
Hydroxysteroid
Oxosteroid
3-beta-hydroxysteroid
Delta-7-steroid
Fatty alcohol
Cyclohexenone
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Ketone
Polyol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

26-hydroxy steroid (CHEBI:19793 )
20-hydroxy steroid (CHEBI:19793 )
Cholesterol and derivatives (LMST01010184 )

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	0.79	ALOGPS
logP	-0.44	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	13.19	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	158.68 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	130.42 m³·mol⁻¹	ChemAxon
Polarizability	54.72 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

C16500

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21123946

PDB ID

Not Available

ChEBI ID

19793

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 20,26-dihydroxyecdysone (NP0181617)

MOL for NP0181617 (20,26-dihydroxyecdysone)

3D MOL for NP0181617 (20,26-dihydroxyecdysone)

3D SDF for NP0181617 (20,26-dihydroxyecdysone)

3D-SDF for NP0181617 (20,26-dihydroxyecdysone)

PDB for NP0181617 (20,26-dihydroxyecdysone)

3D PDB for NP0181617 (20,26-dihydroxyecdysone)

SMILES for NP0181617 (20,26-dihydroxyecdysone)

INCHI for NP0181617 (20,26-dihydroxyecdysone)

Structure for NP0181617 (20,26-dihydroxyecdysone)

3D Structure for NP0181617 (20,26-dihydroxyecdysone)