NP-MRD: Showing NP-Card for MC21-A (NP0004511)

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Record Information

Version

2.0

Created at

2020-12-09 01:58:55 UTC

Updated at

2021-07-15 16:49:23 UTC

NP-MRD ID

NP0004511

Secondary Accession Numbers

None

Natural Product Identification

Common Name

MC21-A

Provided By

NPAtlas

Description

3,3',5,5'-Tetrabromo-[1,1'-biphenyl]-2,2'-diol belongs to the class of organic compounds known as polybrominated biphenyls. These are organic aromatic compounds containing a biphenyl moiety, which is substituted at two or more ring positions by a bromine atom. MC21-A is found in Pseudoalteromonas and Pseudoalteromonas phenolica. MC21-A was first documented in 2003 (PMID: 12543647). Based on a literature review very few articles have been published on 3,3',5,5'-tetrabromo-[1,1'-biphenyl]-2,2'-diol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118073D          

 24 25  0  0  0  0            999 V2000
    0.6122    2.1903   -0.3102 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4067    1.0631   -0.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7668    1.0904   -0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6149    2.7649   -0.4406 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.4997   -0.0647    0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8830   -1.2714    0.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8900   -2.8590    0.6421 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.5100   -1.2855    0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7549   -0.1315    0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6936   -0.2014    0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3900   -0.5176    1.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7660   -0.5723    1.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6860   -1.0101    2.9713 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5032   -0.3135    0.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8299    0.0023   -0.9197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8224    0.3670   -2.5054 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4430    0.0534   -0.9297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7672    0.3693   -2.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0954    3.0660   -0.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5868    0.0185    0.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0059   -2.2398    0.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8030   -0.7217    2.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5943   -0.3588    0.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3277    0.5623   -2.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
  9  2  1  0  0  0  0
 17 10  1  0  0  0  0
  1 19  1  0  0  0  0
  5 20  1  0  0  0  0
  8 21  1  0  0  0  0
 11 22  1  0  0  0  0
 14 23  1  0  0  0  0
 18 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004511

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(Br)C([H])=C(Br)C([H])=C1C1=C([H])C(Br)=C([H])C(Br)=C1O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H6Br4O2/c13-5-1-7(11(17)9(15)3-5)8-2-6(14)4-10(16)12(8)18/h1-4,17-18H

> <INCHI_KEY>
TXODBIOSWNNKJM-UHFFFAOYSA-N

> <FORMULA>
C12H6Br4O2

> <MOLECULAR_WEIGHT>
501.794

> <EXACT_MASS>
497.710131

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
33.98448331334939

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,3',5,5'-tetrabromo-[1,1'-biphenyl]-2,2'-diol

> <ALOGPS_LOGP>
5.96

> <JCHEM_LOGP>
6.088351036

> <ALOGPS_LOGS>
-5.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.7583637191567405

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.904079846942999

> <JCHEM_PKA_STRONGEST_BASIC>
-7.109281340250285

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
85.64720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,3',5,5'-tetrabromo-[1,1'-biphenyl]-2,2'-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0       0.612   2.190  -0.310  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.407   1.063  -0.098  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.767   1.090  -0.112  0.00  0.00           C+0
HETATM    4 Br   UNK     0       3.615   2.765  -0.441  0.00  0.00          Br+0
HETATM    5  C   UNK     0       3.500  -0.065   0.105  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.883  -1.271   0.342  0.00  0.00           C+0
HETATM    7 Br   UNK     0       3.890  -2.859   0.642  0.00  0.00          Br+0
HETATM    8  C   UNK     0       1.510  -1.286   0.354  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.755  -0.132   0.138  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.694  -0.201   0.191  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.390  -0.518   1.349  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.766  -0.572   1.370  0.00  0.00           C+0
HETATM   13 Br   UNK     0      -3.686  -1.010   2.971  0.00  0.00          Br+0
HETATM   14  C   UNK     0      -3.503  -0.314   0.238  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.830   0.002  -0.920  0.00  0.00           C+0
HETATM   16 Br   UNK     0      -3.822   0.367  -2.505  0.00  0.00          Br+0
HETATM   17  C   UNK     0      -1.443   0.053  -0.930  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.767   0.369  -2.096  0.00  0.00           O+0
HETATM   19  H   UNK     0       1.095   3.066  -0.486  0.00  0.00           H+0
HETATM   20  H   UNK     0       4.587   0.019   0.084  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.006  -2.240   0.541  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.803  -0.722   2.237  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.594  -0.359   0.258  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.328   0.562  -2.922  0.00  0.00           H+0
CONECT    1    2   19                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   20                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   21                                                  
CONECT    9    8   10    2                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   23                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   10                                                  
CONECT   18   17   24                                                       
CONECT   19    1                                                            
CONECT   20    5                                                            
CONECT   21    8                                                            
CONECT   22   11                                                            
CONECT   23   14                                                            
CONECT   24   18                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3,3',5,5'-Tetrabromo-2,2'-biphenyldiol	MeSH
MC21-a	MeSH

Chemical Formula

C₁₂H₆Br₄O₂

Average Mass

501.7940 Da

Monoisotopic Mass

497.71013 Da

IUPAC Name

3,3',5,5'-tetrabromo-[1,1'-biphenyl]-2,2'-diol

Traditional Name

3,3',5,5'-tetrabromo-[1,1'-biphenyl]-2,2'-diol

CAS Registry Number

Not Available

SMILES

OC1=C(Br)C=C(Br)C=C1C1=CC(Br)=CC(Br)=C1O

InChI Identifier

InChI=1S/C12H6Br4O2/c13-5-1-7(11(17)9(15)3-5)8-2-6(14)4-10(16)12(8)18/h1-4,17-18H

InChI Key

TXODBIOSWNNKJM-UHFFFAOYSA-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
Pseudoalteromonas	NPAtlas	12543647
Pseudoalteromonas phenolica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as polybrominated biphenyls. These are organic aromatic compounds containing a biphenyl moiety, which is substituted at two or more ring positions by a bromine atom.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Polybrominated biphenyls

Alternative Parents

Substituents

Polybrominated biphenyl
4-halophenol
2-halophenol
2-bromophenol
4-bromophenol
Bromobenzene
Halobenzene
Phenol
Aryl halide
Aryl bromide
Hydrocarbon derivative
Organic oxygen compound
Organohalogen compound
Organobromide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organobromine compound (CHEBI:70620 )
biphenyls (CHEBI:70620 )

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	5.96	ALOGPS
logP	6.09	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	6.9	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.65 m³·mol⁻¹	ChemAxon
Polarizability	33.98 Å³	ChemAxon
Number of Rings	2	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

NPAtlas ID

NPA000964

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28660

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

Not Available

Good Scents ID

Not Available

References

General References

Isnansetyo A, Kamei Y: MC21-A, a bactericidal antibiotic produced by a new marine bacterium, Pseudoalteromonas phenolica sp. nov. O-BC30(T), against methicillin-resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2003 Feb;47(2):480-8. doi: 10.1128/aac.47.2.480-488.2003. [PubMed:12543647 ]

Showing NP-Card for MC21-A (NP0004511)

MOL for NP0004511 (MC21-A)

3D MOL for NP0004511 (MC21-A)

3D SDF for NP0004511 (MC21-A)

3D-SDF for NP0004511 (MC21-A)

PDB for NP0004511 (MC21-A)

3D PDB for NP0004511 (MC21-A)

SMILES for NP0004511 (MC21-A)

INCHI for NP0004511 (MC21-A)

Structure for NP0004511 (MC21-A)

3D Structure for NP0004511 (MC21-A)