NP-MRD: Showing NP-Card for Diaulusterol B (NP0076434)

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Record Information

Version

2.0

Created at

2022-04-28 21:35:31 UTC

Updated at

2022-04-28 21:35:31 UTC

NP-MRD ID

NP0076434

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Diaulusterol B

Description

Diaulusterol B belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Diaulusterol B is found in Diaulula sandiegensis and Synoicum adareanum. Diaulusterol B was first documented in 2007 (PMID: 18039009). Based on a literature review very few articles have been published on diaulusterol B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223352D          

 31 34  0  0  1  0            999 V2000
    4.2475    2.1537    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9323   -0.5144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.0770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5867    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
   -1.6810    2.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873    3.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046    3.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5109    3.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0173    4.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1623    3.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8596    4.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6232    2.4441    0.0000 C   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
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  4  5  1  0  0  0  0
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  7  8  1  6  0  0  0
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  8 12  1  0  0  0  0
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 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  6  0  0  0
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 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
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 23 26  1  0  0  0  0
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 13 28  1  6  0  0  0
  5 29  1  6  0  0  0
  2 30  1  1  0  0  0
  1 31  1  1  0  0  0
M  END

     RDKit          3D

 73 76  0  0  0  0  0  0  0  0999 V2000
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    2.4176    0.4756    0.5183 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -6.3480   -0.8023   -0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2209   -0.1890    0.2297 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2201    0.5047   -0.4649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4814    0.8099    1.0769 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2451    1.9952    1.1981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1622    1.2307    0.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3457   -0.0596    0.2741 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4954   -0.7832    1.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7403    0.8440    1.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0017   -0.0340    0.1831 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3044   -1.3967    0.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1280    2.1728    1.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.4477    1.0591   -0.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0443    1.5013   -0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0648   -2.0582   -1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  1  0
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M  END


  Mrv1652304282223352D          

 31 34  0  0  1  0            999 V2000
    4.2475    2.1537    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9323   -0.5144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 30  1  1  0  0  0
  1 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0076434

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2C3=CC(=O)C4=C[C@H](O)[C@H](O)C[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O4/c1-16(7-6-11-25(2,3)31)18-8-9-19-17-13-22(28)21-14-23(29)24(30)15-27(21,5)20(17)10-12-26(18,19)4/h13-14,16,18-20,23-24,29-31H,6-12,15H2,1-5H3/t16-,18-,19+,20+,23+,24-,26-,27-/m1/s1

> <INCHI_KEY>
NKTPHQGGTBBIOB-LDEZCDJPSA-N

> <FORMULA>
C27H42O4

> <MOLECULAR_WEIGHT>
430.629

> <EXACT_MASS>
430.308309832

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
51.61577890088478

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4R,5S,11R,14R,15R)-4,5-dihydroxy-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,9-dien-8-one

> <ALOGPS_LOGP>
4.29

> <JCHEM_LOGP>
4.009660502333334

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.120349201082085

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.613224268586077

> <JCHEM_PKA_STRONGEST_BASIC>
-1.254436639354736

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
125.17999999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.99e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,5S,11R,14R,15R)-4,5-dihydroxy-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,9-dien-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  C   UNK     0      -3.138   4.882   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.083   6.098   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.609   5.887   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.554   7.103   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -7.499   8.319   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -7.770   6.158   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.338   8.048   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.032   6.519   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.200   5.313   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.897   4.562   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.968   2.301   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.921   5.197   0.000  0.00  0.00           O+0
CONECT    1    2    6   31                                                  
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   29                                             
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                                                  
CONECT   13   12   14   16   28                                             
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   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   19                                                            
CONECT   28   13                                                            
CONECT   29    5                                                            
CONECT   30    2                                                            
CONECT   31    1                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₂O₄

Average Mass

430.6290 Da

Monoisotopic Mass

430.30831 Da

IUPAC Name

(1S,2R,4R,5S,11R,14R,15R)-4,5-dihydroxy-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,9-dien-8-one

Traditional Name

(1S,2R,4R,5S,11R,14R,15R)-4,5-dihydroxy-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,9-dien-8-one

CAS Registry Number

Not Available

SMILES

C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2C3=CC(=O)C4=C[C@H](O)[C@H](O)C[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C27H42O4/c1-16(7-6-11-25(2,3)31)18-8-9-19-17-13-22(28)21-14-23(29)24(30)15-27(21,5)20(17)10-12-26(18,19)4/h13-14,16,18-20,23-24,29-31H,6-12,15H2,1-5H3/t16-,18-,19+,20+,23+,24-,26-,27-/m1/s1

InChI Key

NKTPHQGGTBBIOB-LDEZCDJPSA-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
Diaulula sandiegensis	LOTUS Database	35616633
Synoicum adareanum	-	KNApSAcK

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
25-hydroxysteroid
3-hydroxy-delta-7-steroid
3-hydroxysteroid
6-oxosteroid
3-alpha-hydroxysteroid
Oxosteroid
2-hydroxysteroid
Hydroxysteroid
Delta-7-steroid
Cyclohexenone
Tertiary alcohol
1,2-diol
Secondary alcohol
Ketone
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organooxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	4.29	ALOGPS
logP	4.01	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	125.18 m³·mol⁻¹	ChemAxon
Polarizability	51.62 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

C00039009

Chemspider ID

23311255

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44445498

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Miyata Y, Diyabalanage T, Amsler CD, McClintock JB, Valeriote FA, Baker BJ: Ecdysteroids from the Antarctic tunicate Synoicum adareanum. J Nat Prod. 2007 Dec;70(12):1859-64. doi: 10.1021/np0702739. Epub 2007 Nov 27. [PubMed:18039009 ]

Showing NP-Card for Diaulusterol B (NP0076434)

MOL for NP0076434 (Diaulusterol B)

3D MOL for NP0076434 (Diaulusterol B)

3D SDF for NP0076434 (Diaulusterol B)

3D-SDF for NP0076434 (Diaulusterol B)

PDB for NP0076434 (Diaulusterol B)

3D PDB for NP0076434 (Diaulusterol B)

SMILES for NP0076434 (Diaulusterol B)

INCHI for NP0076434 (Diaulusterol B)

Structure for NP0076434 (Diaulusterol B)

3D Structure for NP0076434 (Diaulusterol B)