NP-MRD: Showing NP-Card for 3-dehydro-2-deoxyecdysone (NP0299453)

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Record Information

Version

2.0

Created at

2022-09-10 11:17:00 UTC

Updated at

2022-09-10 11:17:01 UTC

NP-MRD ID

NP0299453

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-dehydro-2-deoxyecdysone

Description

(1R,2R,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-ene-5,8-dione belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. 3-dehydro-2-deoxyecdysone is found in Locusta migratoria. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups (1R,2R,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-ene-5,8-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv1652301251922262D          

 34 37  0  0  1  0            999 V2000
   22.5756  -20.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5756  -21.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2900  -21.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0046  -21.2619    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.0046  -20.4369    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.2900  -20.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7190  -21.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4334  -21.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4334  -20.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7190  -20.0244    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.1479  -20.0244    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.1479  -19.1994    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.4334  -18.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7190  -19.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5768  -20.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5768  -19.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8624  -18.7870    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.8624  -17.9620    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.0046  -19.6120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0046  -22.0869    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.8612  -21.6744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1479  -18.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5792  -17.5481    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.1502  -17.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2849  -17.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9839  -17.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6862  -17.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3869  -17.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6862  -18.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4006  -18.3701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1479  -20.8494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7190  -22.4994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5792  -16.7246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7190  -20.8494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  4  5  1  0  0  0  0
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  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
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  8  9  2  0  0  0  0
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  5 10  1  0  0  0  0
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 16 17  1  0  0  0  0
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 17 18  1  1  0  0  0
  5 19  1  1  0  0  0
  4 20  1  1  0  0  0
  2 21  2  0  0  0  0
 12 22  1  1  0  0  0
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 27 30  1  0  0  0  0
 11 31  1  6  0  0  0
  7 32  2  0  0  0  0
 23 33  1  6  0  0  0
 10 34  1  6  0  0  0
M  END

     RDKit          3D

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M  END

 
  Mrv1652301251922262D          

 34 37  0  0  1  0            999 V2000
   22.5756  -20.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 21  2  0  0  0  0
 12 22  1  1  0  0  0
 18 23  1  0  0  0  0
 18 24  1  6  0  0  0
 23 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
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 11 31  1  6  0  0  0
  7 32  2  0  0  0  0
 23 33  1  6  0  0  0
 10 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0299453

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O5/c1-16(22(29)9-10-24(2,3)31)18-8-13-27(32)20-15-23(30)21-14-17(28)6-11-25(21,4)19(20)7-12-26(18,27)5/h15-16,18-19,21-22,29,31-32H,6-14H2,1-5H3/t16-,18+,19-,21-,22+,25+,26+,27+/m0/s1

> <INCHI_KEY>
PDQPHVPWJVSDEA-IHTFJKPZSA-N

> <FORMULA>
C27H42O5

> <MOLECULAR_WEIGHT>
446.628

> <EXACT_MASS>
446.303224452

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
51.107020685999835

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-ene-5,8-dione

> <ALOGPS_LOGP>
3.25

> <JCHEM_LOGP>
2.973612648333334

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.843175794078498

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.742916076888552

> <JCHEM_PKA_STRONGEST_BASIC>
-2.627362688414686

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
125.03509999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-ene-5,8-dione

> <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      42.141 -38.149   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      42.141 -39.689   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      43.475 -40.459   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      44.809 -39.689   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      44.809 -38.149   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      43.475 -37.379   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      46.142 -40.459   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      47.476 -39.689   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      47.476 -38.149   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      46.142 -37.379   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      48.809 -37.379   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      48.809 -35.839   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      47.476 -35.069   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      46.142 -35.839   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      51.477 -37.379   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      51.477 -35.839   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      50.143 -35.069   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      50.143 -33.529   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      44.809 -36.609   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      44.809 -41.229   0.000  0.00  0.00           H+0
HETATM   21  O   UNK     0      40.808 -40.459   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      48.809 -34.299   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      51.481 -32.756   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      48.814 -32.761   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      52.798 -33.517   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      54.103 -32.764   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      55.414 -33.521   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      56.722 -32.766   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      55.414 -35.069   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      56.748 -34.291   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      48.809 -38.919   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      46.142 -41.999   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      51.481 -31.219   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0      46.142 -38.919   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   20                                             
CONECT    5    4    6   10   19                                             
CONECT    6    5    1                                                       
CONECT    7    4    8   32                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    5   14   34                                             
CONECT   11    9   12   15   31                                             
CONECT   12   11   13   17   22                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   23   24                                                  
CONECT   19    5                                                            
CONECT   20    4                                                            
CONECT   21    2                                                            
CONECT   22   12                                                            
CONECT   23   18   25   33                                                  
CONECT   24   18                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   11                                                            
CONECT   32    7                                                            
CONECT   33   23                                                            
CONECT   34   10                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₂O₅

Average Mass

446.6280 Da

Monoisotopic Mass

446.30322 Da

IUPAC Name

(1R,2R,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-ene-5,8-dione

Traditional Name

(1R,2R,7R,11S,14R,15R)-14-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-ene-5,8-dione

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H42O5/c1-16(22(29)9-10-24(2,3)31)18-8-13-27(32)20-15-23(30)21-14-17(28)6-11-25(21,4)19(20)7-12-26(18,27)5/h15-16,18-19,21-22,29,31-32H,6-14H2,1-5H3/t16-,18+,19-,21-,22+,25+,26+,27+/m0/s1

InChI Key

PDQPHVPWJVSDEA-IHTFJKPZSA-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
Locusta migratoria	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
Cholestane-skeleton
Ecdysteroid
Trihydroxy bile acid, alcohol, or derivatives
25-hydroxysteroid
22-hydroxysteroid
3-oxo-delta-7-steroid
3-oxosteroid
3-oxo-5-beta-steroid
6-oxosteroid
14-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-7-steroid
Cyclohexenone
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Cyclic ketone
Ketone
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid (CHEBI:80532 )

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	3.25	ALOGPS
logP	2.97	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.74	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	125.04 m³·mol⁻¹	ChemAxon
Polarizability	51.11 Å³	ChemAxon
Number of Rings	4	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

Not Available

KEGG Compound ID

C16497

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15251159

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-dehydro-2-deoxyecdysone (NP0299453)

MOL for NP0299453 (3-dehydro-2-deoxyecdysone)

3D MOL for NP0299453 (3-dehydro-2-deoxyecdysone)

3D SDF for NP0299453 (3-dehydro-2-deoxyecdysone)

3D-SDF for NP0299453 (3-dehydro-2-deoxyecdysone)

PDB for NP0299453 (3-dehydro-2-deoxyecdysone)

3D PDB for NP0299453 (3-dehydro-2-deoxyecdysone)

SMILES for NP0299453 (3-dehydro-2-deoxyecdysone)

INCHI for NP0299453 (3-dehydro-2-deoxyecdysone)

Structure for NP0299453 (3-dehydro-2-deoxyecdysone)

3D Structure for NP0299453 (3-dehydro-2-deoxyecdysone)