NP-MRD: Showing NP-Card for callophycoic acid B (NP0025206)

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Record Information

Version

2.0

Created at

2021-06-19 17:23:33 UTC

Updated at

2021-06-29 23:49:59 UTC

NP-MRD ID

NP0025206

Secondary Accession Numbers

None

Natural Product Identification

Common Name

callophycoic acid B

Provided By

JEOL Database JEOL Logo

Description

Callophycoic acid B is also known as callophycoate b. Callophycoic acid B is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. callophycoic acid B is found in Callophycus serratus. callophycoic acid B was first documented in 2018 (PMID: 30407005). Based on a literature review very few articles have been published on callophycoic acid B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119233D          

 66 68  0  0  0  0            999 V2000
    6.3678   -2.5975    0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3527   -1.8625   -0.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3415   -2.2578   -2.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5028   -0.9282   -0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4464   -0.3745    1.1595 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4023   -1.0507    2.0590 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9461   -0.8430    1.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5098    0.5930    1.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1275   -1.9072    1.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3409   -1.9037    1.2221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7957   -2.9069    0.1472 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 66 68  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306192119233D          

 66 68  0  0  0  0            999 V2000
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    1.5555   -1.1013   -4.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9  7  2  0  0  0  0
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  7  8  1  0  0  0  0
 31 18  1  0  0  0  0
  7  6  1  0  0  0  0
 22 21  2  0  0  0  0
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 18 17  1  0  0  0  0
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  4  2  2  3  0  0  0
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  2  3  1  0  0  0  0
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 13 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025206

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C([H])=C2OC([H])=C3C([H])([H])C([H])([H])[C@]([H])(Br)[C@@](C([H])([H])[H])(C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])[C@]3([H])C([H])([H])C2=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H35BrO3/c1-18(2)7-5-8-19(3)9-6-14-27(4)23-16-22-15-20(26(29)30)10-12-24(22)31-17-21(23)11-13-25(27)28/h7,9-10,12,15,17,23,25H,5-6,8,11,13-14,16H2,1-4H3,(H,29,30)/b19-9+/t23-,25+,27+/m1/s1

> <INCHI_KEY>
QVXPDENFBGGWAY-FXSXARLRSA-N

> <FORMULA>
C27H35BrO3

> <MOLECULAR_WEIGHT>
487.478

> <EXACT_MASS>
486.176958

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
50.709418697708

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,14S,15S)-14-bromo-15-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-15-methyl-9-oxatricyclo[9.4.0.0^{3,8}]pentadeca-3,5,7,10-tetraene-5-carboxylic acid

> <ALOGPS_LOGP>
7.22

> <JCHEM_LOGP>
7.585724953000001

> <ALOGPS_LOGS>
-6.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.307864958605717

> <JCHEM_PKA_STRONGEST_BASIC>
-5.256962127626353

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
132.79139999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.80e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,14S,15S)-14-bromo-15-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-15-methyl-9-oxatricyclo[9.4.0.0^{3,8}]pentadeca-3,5,7,10-tetraene-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 66 68  0  0  0  0  0  0  0  0999 V2000
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 13 53  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       6.368  -2.598   0.124  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.353  -1.863  -0.708  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.341  -2.258  -2.160  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.503  -0.928  -0.239  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.446  -0.375   1.159  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.402  -1.051   2.059  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.946  -0.843   1.667  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.510   0.593   1.542  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.127  -1.907   1.531  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.341  -1.904   1.222  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.796  -2.907   0.147  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.399  -2.657  -1.354  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.281  -3.626  -2.200  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.118  -2.937  -1.613  0.00  0.00           C+0
HETATM   15 Br   UNK     0       1.688  -4.761  -1.149  0.00  0.00          Br+0
HETATM   16  C   UNK     0       1.545  -2.687  -3.060  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.266  -1.246  -3.452  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.178  -0.869  -3.216  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.859  -0.287  -4.223  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.128   0.241  -4.215  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.402   1.127  -3.201  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.688   2.449  -3.539  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.975   3.373  -2.532  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.987   2.966  -1.191  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.279   3.911  -0.086  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.295   3.638   1.100  0.00  0.00           O+0
HETATM   27  O   UNK     0      -3.537   5.158  -0.518  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.720   1.628  -0.864  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.436   0.698  -1.872  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.175  -0.751  -1.565  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.694  -1.153  -1.795  0.00  0.00           C+0
HETATM   32  H   UNK     0       6.272  -2.403   1.194  0.00  0.00           H+0
HETATM   33  H   UNK     0       6.253  -3.678  -0.013  0.00  0.00           H+0
HETATM   34  H   UNK     0       7.381  -2.317  -0.183  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.647  -1.650  -2.749  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.048  -3.307  -2.267  0.00  0.00           H+0
HETATM   37  H   UNK     0       6.338  -2.129  -2.595  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.788  -0.477  -0.926  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.428  -0.454   1.641  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.255   0.704   1.095  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.527  -0.657   3.077  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.635  -2.122   2.125  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.924   1.187   2.364  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.426   0.723   1.584  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.863   1.016   0.596  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.545  -2.901   1.698  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.854  -2.178   2.154  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.709  -0.907   0.974  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.892  -2.940   0.210  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.488  -3.913   0.457  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.347  -3.481  -1.996  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.142  -3.489  -3.276  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.072  -4.675  -1.969  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.733  -2.304  -0.970  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.039  -3.372  -3.751  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.616  -2.883  -3.181  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.901  -0.574  -2.860  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.556  -1.101  -4.500  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.443  -0.150  -5.216  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.678   2.760  -4.580  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.188   4.404  -2.803  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.711   5.661   0.305  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.740   1.314   0.178  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.852  -1.355  -2.180  0.00  0.00           H+0
HETATM   65  H   UNK     0      -2.474  -0.940  -0.529  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.086  -0.501  -1.150  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   35   36   37                                             
CONECT    4    5    2   38                                                  
CONECT    5    6    4   39   40                                             
CONECT    6    7    5   41   42                                             
CONECT    7    9    8    6                                                  
CONECT    8    7   43   44   45                                             
CONECT    9   10    7   46                                                  
CONECT   10   11    9   47   48                                             
CONECT   11   12   10   49   50                                             
CONECT   12   14   31   11   13                                             
CONECT   13   12   51   52   53                                             
CONECT   14   12   16   15   54                                             
CONECT   15   14                                                            
CONECT   16   17   14   55   56                                             
CONECT   17   18   16   57   58                                             
CONECT   18   19   31   17                                                  
CONECT   19   20   18   59                                                  
CONECT   20   21   19                                                       
CONECT   21   20   22   29                                                  
CONECT   22   23   21   60                                                  
CONECT   23   24   22   61                                                  
CONECT   24   25   23   28                                                  
CONECT   25   24   27   26                                                  
CONECT   26   25                                                            
CONECT   27   25   62                                                       
CONECT   28   29   24   63                                                  
CONECT   29   28   21   30                                                  
CONECT   30   31   29   64   65                                             
CONECT   31   12   30   18   66                                             
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42    6                                                            
CONECT   43    8                                                            
CONECT   44    8                                                            
CONECT   45    8                                                            
CONECT   46    9                                                            
CONECT   47   10                                                            
CONECT   48   10                                                            
CONECT   49   11                                                            
CONECT   50   11                                                            
CONECT   51   13                                                            
CONECT   52   13                                                            
CONECT   53   13                                                            
CONECT   54   14                                                            
CONECT   55   16                                                            
CONECT   56   16                                                            
CONECT   57   17                                                            
CONECT   58   17                                                            
CONECT   59   19                                                            
CONECT   60   22                                                            
CONECT   61   23                                                            
CONECT   62   27                                                            
CONECT   63   28                                                            
CONECT   64   30                                                            
CONECT   65   30                                                            
CONECT   66   31                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  136    0
END

RDKit          3D

66 68  0  0  0  0  0  0  0  0999 V2000
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   -0.3990   -2.6572   -1.3544 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.1181   -2.9365   -1.6133 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.4743   -0.9403   -0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0862   -0.5010   -1.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
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 13 51  1  0
 13 52  1  0
 13 53  1  0
M  END

View in JSmol

Synonyms

Value	Source
Callophycoate b	Generator

Chemical Formula

C₂₇H₃₅BrO₃

Average Mass

487.4780 Da

Monoisotopic Mass

486.17696 Da

IUPAC Name

(1R,14S,15S)-14-bromo-15-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-15-methyl-9-oxatricyclo[9.4.0.0^{3,8}]pentadeca-3,5,7,10-tetraene-5-carboxylic acid

Traditional Name

(1R,14S,15S)-14-bromo-15-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-15-methyl-9-oxatricyclo[9.4.0.0^{3,8}]pentadeca-3,5,7,10-tetraene-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C([H])C([H])=C2OC([H])=C3C([H])([H])C([H])([H])[C@]([H])(Br)[C@@](C([H])([H])[H])(C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])[C@]3([H])C([H])([H])C2=C1[H]

InChI Identifier

InChI=1S/C27H35BrO3/c1-18(2)7-5-8-19(3)9-6-14-27(4)23-16-22-15-20(26(29)30)10-12-24(22)31-17-21(23)11-13-25(27)28/h7,9-10,12,15,17,23,25H,5-6,8,11,13-14,16H2,1-4H3,(H,29,30)/b19-9+/t23-,25+,27+/m1/s1

InChI Key

QVXPDENFBGGWAY-FXSXARLRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Callophycus serratus	JEOL database	Lane, A. L., et al, J. Org. Chem. 72, 7343 (2007)

Chemical Taxonomy

Classification

Not classified

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	7.22	ALOGPS
logP	7.59	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	4.31	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	132.79 m³·mol⁻¹	ChemAxon
Polarizability	50.71 Å³	ChemAxon
Number of Rings	3	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

23076454

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

65558

Good Scents ID

Not Available

References

General References

Woolner VH, Gordon RMA, Miller JH, Lein M, Northcote PT, Keyzers RA: Halogenated Meroditerpenoids from a South Pacific Collection of the Red Alga Callophycus serratus. J Nat Prod. 2018 Nov 26;81(11):2446-2454. doi: 10.1021/acs.jnatprod.8b00487. Epub 2018 Nov 8. [PubMed:30407005 ]
Lane, A. L., et al. (2007). Lane, A. L., et al, J. Org. Chem. 72, 7343 (2007). J. Org. Chem..

Showing NP-Card for callophycoic acid B (NP0025206)

MOL for NP0025206 (callophycoic acid B)

3D MOL for NP0025206 (callophycoic acid B)

3D SDF for NP0025206 (callophycoic acid B)

3D-SDF for NP0025206 (callophycoic acid B)

PDB for NP0025206 (callophycoic acid B)

3D PDB for NP0025206 (callophycoic acid B)

SMILES for NP0025206 (callophycoic acid B)

INCHI for NP0025206 (callophycoic acid B)

Structure for NP0025206 (callophycoic acid B)

3D Structure for NP0025206 (callophycoic acid B)