NP-MRD: Showing NP-Card for (-)-Danielid (NP0081987)

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Record Information

Version

2.0

Created at

2022-04-29 03:02:36 UTC

Updated at

2022-04-29 03:02:36 UTC

NP-MRD ID

NP0081987

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Danielid

Description

Methyl (2S,3S,5R,11S,17R)-2,17-bis(acetyloxy)-3-hydroxy-3-methyl-7-oxo-11-(prop-1-en-2-yl)-6,16-dioxatricyclo[11.2.1.1⁵,⁸]Heptadeca-1(15),8,13-triene-14-carboxylate belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (-)-Danielid is found in Sinularia asterolobata. Based on a literature review very few articles have been published on methyl (2S,3S,5R,11S,17R)-2,17-bis(acetyloxy)-3-hydroxy-3-methyl-7-oxo-11-(prop-1-en-2-yl)-6,16-dioxatricyclo[11.2.1.1⁵,⁸]Heptadeca-1(15),8,13-triene-14-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205022D          

 35 37  0  0  1  0            999 V2000
    2.5935    0.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1600    0.0038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9240   -0.7867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4905   -1.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2545   -2.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4518   -2.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8853   -1.7680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0827   -1.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5161   -1.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7366   -0.4837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3831    0.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828    0.8283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7069    0.4330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5989    1.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0590    1.1791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8769    1.6464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1154    1.9638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5402    1.4631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0095    2.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3542   -0.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2158   -3.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1732   -0.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9502   -1.1426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9823   -0.0628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1213   -0.9775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548   -0.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7933   -0.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2811    0.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 11 12  1  0  0  0  0
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  1 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  1  0  0  0
 12 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 20  2  0  0  0  0
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  9 21  2  0  0  0  0
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  4 29  1  0  0  0  0
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 33 35  1  0  0  0  0
M  END

     RDKit          3D

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    0.2835   -3.8821   -0.7776 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5607   -2.4663   -4.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  2  3
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 29 28  1  0
  8  7  1  0
 27 57  1  0
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 30 60  1  0
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  1 37  1  0
M  END


  Mrv1652304292205022D          

 35 37  0  0  1  0            999 V2000
    2.5935    0.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1600    0.0038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.4518   -2.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8853   -1.7680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0827   -1.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3542   -0.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2868   -1.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1213   -0.9775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7933   -0.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2811    0.4004    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 20 21  1  0  0  0  0
  9 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
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  7 26  1  1  0  0  0
 26 27  2  0  0  0  0
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  4 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  2 31  1  1  0  0  0
  3 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0081987

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C2C[C@H](C\C=C3/[C@@H](OC(C)=O)[C@@H](C[C@](C)(O)[C@H](OC(C)=O)C(O2)=C1)OC3=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O10/c1-12(2)15-7-8-16-21(32-13(3)26)20(35-24(16)29)11-25(5,30)22(33-14(4)27)19-10-17(23(28)31-6)18(9-15)34-19/h8,10,15,20-22,30H,1,7,9,11H2,2-6H3/b16-8+/t15-,20+,21+,22+,25-/m0/s1

> <INCHI_KEY>
XOPXSSDJKFTOQG-GZOBIPNWSA-N

> <FORMULA>
C25H30O10

> <MOLECULAR_WEIGHT>
490.505

> <EXACT_MASS>
490.183897166

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
49.44657339811992

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,3S,5R,11S,17R)-2,17-bis(acetyloxy)-3-hydroxy-3-methyl-7-oxo-11-(prop-1-en-2-yl)-6,16-dioxatricyclo[11.2.1.1^{5,8}]heptadeca-1(15),8,13-triene-14-carboxylate

> <ALOGPS_LOGP>
2.19

> <JCHEM_LOGP>
2.041231137333333

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.645017838376283

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0757093905482424

> <JCHEM_POLAR_SURFACE_AREA>
138.57000000000002

> <JCHEM_REFRACTIVITY>
121.34479999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,3S,5R,11S,17R)-2,17-bis(acetyloxy)-3-hydroxy-3-methyl-7-oxo-11-(prop-1-en-2-yl)-6,16-dioxatricyclo[11.2.1.1^{5,8}]heptadeca-1(15),8,13-triene-14-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       4.841   1.126   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.899   0.007   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.458  -1.469   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.516  -2.588   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.075  -4.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.577  -4.420   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.519  -3.300   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.021  -3.657   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.963  -2.537   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.375  -0.903   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.715   0.488   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.834   1.546   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.186   0.808   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.985   2.335   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.843   2.201   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.637   3.073   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.215   3.666   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.008   2.731   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.018   5.193   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.661  -0.648   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.535  -2.183   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.703  -3.187   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.417  -4.700   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -3.156  -2.677   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.324  -3.682   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.079  -4.776   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.580  -5.132   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.136  -5.895   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.790  -1.615   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.240  -2.133   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       7.434  -0.117   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       3.960  -1.825   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.902  -0.705   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.481  -0.113   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.391   0.747   0.000  0.00  0.00           C+0
CONECT    1    2   13                                                       
CONECT    2    1    3   31                                                  
CONECT    3    2    4   32                                                  
CONECT    4    3    5   29                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   26                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12    1   14   15                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   11   21                                                       
CONECT   21   20    9   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26    7   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    4   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    2                                                       
CONECT   32    3   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2S,3S,5R,11S,17R)-2,17-bis(acetyloxy)-3-hydroxy-3-methyl-7-oxo-11-(prop-1-en-2-yl)-6,16-dioxatricyclo[11.2.1.1,]heptadeca-1(15),8,13-triene-14-carboxylic acid	Generator

Chemical Formula

C₂₅H₃₀O₁₀

Average Mass

490.5050 Da

Monoisotopic Mass

490.18390 Da

IUPAC Name

methyl (2S,3S,5R,11S,17R)-2,17-bis(acetyloxy)-3-hydroxy-3-methyl-7-oxo-11-(prop-1-en-2-yl)-6,16-dioxatricyclo[11.2.1.1^{5,8}]heptadeca-1(15),8,13-triene-14-carboxylate

Traditional Name

methyl (2S,3S,5R,11S,17R)-2,17-bis(acetyloxy)-3-hydroxy-3-methyl-7-oxo-11-(prop-1-en-2-yl)-6,16-dioxatricyclo[11.2.1.1^{5,8}]heptadeca-1(15),8,13-triene-14-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C2C[C@H](C\C=C3/[C@@H](OC(C)=O)[C@@H](C[C@](C)(O)[C@H](OC(C)=O)C(O2)=C1)OC3=O)C(C)=C

InChI Identifier

InChI=1S/C25H30O10/c1-12(2)15-7-8-16-21(32-13(3)26)20(35-24(16)29)11-25(5,30)22(33-14(4)27)19-10-17(23(28)31-6)18(9-15)34-19/h8,10,15,20-22,30H,1,7,9,11H2,2-6H3/b16-8+/t15-,20+,21+,22+,25-/m0/s1

InChI Key

XOPXSSDJKFTOQG-GZOBIPNWSA-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
Sinularia asterolobata	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Macrolide
Furoic acid ester
Furoic acid or derivatives
Furan-3-carboxylic acid ester
Furan-3-carboxylic acid or derivatives
Gamma butyrolactone
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Furan
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.19	ALOGPS
logP	2.04	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.65	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	138.57 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	121.34 m³·mol⁻¹	ChemAxon
Polarizability	49.45 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163106595

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Danielid (NP0081987)

MOL for NP0081987 ((-)-Danielid)

3D MOL for NP0081987 ((-)-Danielid)

3D SDF for NP0081987 ((-)-Danielid)

3D-SDF for NP0081987 ((-)-Danielid)

PDB for NP0081987 ((-)-Danielid)

3D PDB for NP0081987 ((-)-Danielid)

SMILES for NP0081987 ((-)-Danielid)

INCHI for NP0081987 ((-)-Danielid)

Structure for NP0081987 ((-)-Danielid)

3D Structure for NP0081987 ((-)-Danielid)