NP-MRD: Showing NP-Card for bromophycolide N (NP0038769)

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Record Information

Version

2.0

Created at

2021-06-20 21:22:30 UTC

Updated at

2021-06-30 00:11:44 UTC

NP-MRD ID

NP0038769

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bromophycolide N

Provided By

JEOL Database JEOL Logo

Description

SCHEMBL12376402 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. bromophycolide N is found in Callophycus serratus. bromophycolide N was first documented in 2009 (Lane, A. L., et al.). Based on a literature review very few articles have been published on SCHEMBL12376402.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123223D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202123223D          

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M  END
> <DATABASE_ID>
NP0038769

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C([H])=C(C([H])=C1[H])C(=O)O[C@]([H])(C(=C([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@@](O[H])(C([H])([H])[H])[C@]([H])(Br)C([H])([H])C([H])([H])[C@]1(C([H])([H])[H])[C@@]([H])(Br)C([H])([H])C([H])=C(C([H])([H])[H])[C@@]1([H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H36Br2O4/c1-16(2)22-10-13-27(5,32)24(29)11-12-26(4)20(17(3)6-9-23(26)28)15-19-14-18(25(31)33-22)7-8-21(19)30/h6-8,14,20,22-24,30,32H,1,9-13,15H2,2-5H3/t20-,22+,23+,24-,26+,27+/m1/s1

> <INCHI_KEY>
YGMMQPFJIJSNBX-LXZFFOPQSA-N

> <FORMULA>
C27H36Br2O4

> <MOLECULAR_WEIGHT>
584.389

> <EXACT_MASS>
582.098036

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
56.03973605441753

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,7S,8S,11R,12S,15S)-7,11-dibromo-12,21-dihydroxy-4,8,12-trimethyl-15-(prop-1-en-2-yl)-16-oxatricyclo[16.3.1.0^{3,8}]docosa-1(21),4,18(22),19-tetraen-17-one

> <ALOGPS_LOGP>
6.49

> <JCHEM_LOGP>
6.953227509333334

> <ALOGPS_LOGS>
-5.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.047599735154048

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.751536284349413

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2153808365771575

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
140.9211

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,7S,8S,11R,12S,15S)-7,11-dibromo-12,21-dihydroxy-4,8,12-trimethyl-15-(prop-1-en-2-yl)-16-oxatricyclo[16.3.1.0^{3,8}]docosa-1(21),4,18(22),19-tetraen-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 69 71  0  0  0  0  0  0  0  0999 V2000
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 15 55  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.456   4.241   4.416  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.929   3.329   3.579  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.516   2.924   3.702  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.765   2.726   2.462  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.567   1.472   2.869  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.723   0.320   3.438  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.437  -1.059   3.507  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.777  -0.891   4.247  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.595  -1.882   4.335  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.574  -1.734   2.097  0.00  0.00           C+0
HETATM   11 Br   UNK     0      -3.623  -3.419   2.291  0.00  0.00          Br+0
HETATM   12  C   UNK     0      -1.221  -2.116   1.444  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.331  -2.645  -0.005  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.018  -3.072  -0.706  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.365  -3.810  -2.025  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.875  -4.005   0.204  0.00  0.00           C+0
HETATM   17 Br   UNK     0      -0.082  -5.610   0.822  0.00  0.00          Br+0
HETATM   18  C   UNK     0       2.169  -4.471  -0.463  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.920  -3.328  -1.063  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.388  -2.115  -1.305  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.290  -1.006  -1.779  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.905  -1.784  -1.049  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.287  -0.941  -2.219  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.399   0.566  -2.077  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.158   1.191  -0.950  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.131   2.585  -0.802  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.449   3.374  -1.798  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.996   2.770  -2.932  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.958   1.380  -3.069  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.458   0.800  -4.199  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.771   3.249   0.363  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.097   4.423   0.383  0.00  0.00           O+0
HETATM   33  O   UNK     0      -0.946   2.337   1.347  0.00  0.00           O+0
HETATM   34  H   UNK     0      -2.489   4.564   4.329  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.866   4.697   5.205  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.075   3.217   2.808  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.616   1.845   3.837  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.001   3.403   4.559  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.503   3.466   2.123  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.327   1.761   3.604  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.098   1.115   1.978  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.410   0.595   4.455  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.786   0.221   2.883  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.171  -1.845   4.614  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.535  -0.418   3.616  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.645  -0.277   5.146  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.011  -2.764   4.386  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.173  -1.115   1.422  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.571  -1.240   1.427  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.727  -2.859   2.077  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.835  -1.879  -0.605  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.006  -3.507  -0.027  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.505  -3.995  -2.662  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.843  -4.775  -1.830  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.084  -3.237  -2.619  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.139  -3.483   1.131  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.809  -4.952   0.288  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.985  -5.224  -1.239  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.972  -3.513  -1.271  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.102  -0.775  -2.830  0.00  0.00           H+0
HETATM   61  H   UNK     0       3.144  -0.106  -1.174  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.349  -1.274  -1.694  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.926  -1.168  -0.142  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.710  -1.278  -3.172  0.00  0.00           H+0
HETATM   65  H   UNK     0      -0.790  -1.122  -2.309  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.647   0.579  -0.196  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.463   4.458  -1.701  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.433   3.399  -3.702  0.00  0.00           H+0
HETATM   69  H   UNK     0       1.784   1.493  -4.797  0.00  0.00           H+0
CONECT    1    2   34   35                                                  
CONECT    2    4    3    1                                                  
CONECT    3    2   36   37   38                                             
CONECT    4   33    5    2   39                                             
CONECT    5    4    6   40   41                                             
CONECT    6    5    7   42   43                                             
CONECT    7    9    6    8   10                                             
CONECT    8    7   44   45   46                                             
CONECT    9    7   47                                                       
CONECT   10   12   11    7   48                                             
CONECT   11   10                                                            
CONECT   12   10   13   49   50                                             
CONECT   13   12   14   51   52                                             
CONECT   14   22   16   13   15                                             
CONECT   15   14   53   54   55                                             
CONECT   16   14   18   17   56                                             
CONECT   17   16                                                            
CONECT   18   19   16   57   58                                             
CONECT   19   20   18   59                                                  
CONECT   20   22   19   21                                                  
CONECT   21   20   60   61   62                                             
CONECT   22   14   20   23   63                                             
CONECT   23   24   22   64   65                                             
CONECT   24   29   23   25                                                  
CONECT   25   26   24   66                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28   67                                                  
CONECT   28   27   29   68                                                  
CONECT   29   24   30   28                                                  
CONECT   30   29   69                                                       
CONECT   31   32   33   26                                                  
CONECT   32   31                                                            
CONECT   33   31    4                                                       
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    3                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    5                                                            
CONECT   42    6                                                            
CONECT   43    6                                                            
CONECT   44    8                                                            
CONECT   45    8                                                            
CONECT   46    8                                                            
CONECT   47    9                                                            
CONECT   48   10                                                            
CONECT   49   12                                                            
CONECT   50   12                                                            
CONECT   51   13                                                            
CONECT   52   13                                                            
CONECT   53   15                                                            
CONECT   54   15                                                            
CONECT   55   15                                                            
CONECT   56   16                                                            
CONECT   57   18                                                            
CONECT   58   18                                                            
CONECT   59   19                                                            
CONECT   60   21                                                            
CONECT   61   21                                                            
CONECT   62   21                                                            
CONECT   63   22                                                            
CONECT   64   23                                                            
CONECT   65   23                                                            
CONECT   66   25                                                            
CONECT   67   27                                                            
CONECT   68   28                                                            
CONECT   69   30                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  142    0
END

RDKit          3D

69 71  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₆Br₂O₄

Average Mass

584.3890 Da

Monoisotopic Mass

582.09804 Da

IUPAC Name

(3R,7S,8S,11R,12S,15S)-7,11-dibromo-12,21-dihydroxy-4,8,12-trimethyl-15-(prop-1-en-2-yl)-16-oxatricyclo[16.3.1.0^{3,8}]docosa-1(21),4,18(22),19-tetraen-17-one

Traditional Name

(3R,7S,8S,11R,12S,15S)-7,11-dibromo-12,21-dihydroxy-4,8,12-trimethyl-15-(prop-1-en-2-yl)-16-oxatricyclo[16.3.1.0^{3,8}]docosa-1(21),4,18(22),19-tetraen-17-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C([H])=C(C([H])=C1[H])C(=O)O[C@]([H])(C(=C([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@@](O[H])(C([H])([H])[H])[C@]([H])(Br)C([H])([H])C([H])([H])[C@]1(C([H])([H])[H])[C@@]([H])(Br)C([H])([H])C([H])=C(C([H])([H])[H])[C@@]1([H])C2([H])[H]

InChI Identifier

InChI=1S/C27H36Br2O4/c1-16(2)22-10-13-27(5,32)24(29)11-12-26(4)20(17(3)6-9-23(26)28)15-19-14-18(25(31)33-22)7-8-21(19)30/h6-8,14,20,22-24,30,32H,1,9-13,15H2,2-5H3/t20-,22+,23+,24-,26+,27+/m1/s1

InChI Key

YGMMQPFJIJSNBX-LXZFFOPQSA-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. 74, 2736 (2009)

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

Macrolide
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Tertiary alcohol
Bromohydrin
Carboxylic acid ester
Halohydrin
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Alkyl halide
Alkyl bromide
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Organohalogen compound
Organobromide
Organooxygen compound
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	6.49	ALOGPS
logP	6.95	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	8.75	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	140.92 m³·mol⁻¹	ChemAxon
Polarizability	56.04 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

27024134

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42599773

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lane, A. L., et al. (2009). Lane, A. L., et al, J. Org. Chem. 74, 2736 (2009). J. Org. Chem..

Showing NP-Card for bromophycolide N (NP0038769)

MOL for NP0038769 (bromophycolide N)

3D MOL for NP0038769 (bromophycolide N)

3D SDF for NP0038769 (bromophycolide N)

3D-SDF for NP0038769 (bromophycolide N)

PDB for NP0038769 (bromophycolide N)

3D PDB for NP0038769 (bromophycolide N)

SMILES for NP0038769 (bromophycolide N)

INCHI for NP0038769 (bromophycolide N)

Structure for NP0038769 (bromophycolide N)

3D Structure for NP0038769 (bromophycolide N)