NP-MRD: Showing NP-Card for urceolatol (NP0196211)

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Record Information

Version

2.0

Created at

2022-09-04 14:15:11 UTC

Updated at

2022-09-04 14:15:11 UTC

NP-MRD ID

NP0196211

Secondary Accession Numbers

None

Natural Product Identification

Common Name

urceolatol

Description

Urceolatol 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. urceolatol is found in Polysiphonia stricta and Polysiphonia urceolata. urceolatol was first documented in 2006 (PMID: 16864451). Based on a literature review very few articles have been published on urceolatol (PMID: 18088100).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
   -1.4318    4.3235   -1.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3996    2.9349   -1.2905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2245    2.5339   -0.6670 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5458    1.7897   -1.6022 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8288    0.4562   -1.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5034   -0.1470   -2.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8657    0.6314   -3.7284 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7832   -1.4894   -2.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868   -2.3817   -4.0307 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.3921   -2.2132   -1.5017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7467   -1.6389   -0.4674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4379   -0.2684   -0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2534    0.3854    0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5260    1.7323    0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495    2.3491    1.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5142    1.6177    2.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3808    2.4579    4.2229 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2357    0.2810    2.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5892   -0.4648    3.8990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5985   -0.3938    1.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3090   -1.7172    1.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4151   -2.4317    0.7432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2269   -3.6210    0.4776 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5308   -4.7185    0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4033    4.7333   -0.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5533    4.7621   -1.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3848    4.6453   -1.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3784    3.4065   -0.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3492    0.2042   -4.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6166   -3.2780   -1.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3738    3.3948    1.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0551   -0.0205    4.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4175   -2.6394    1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5294   -4.7331    0.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0156   -5.6321    0.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5664   -4.8506    1.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 14  3  1  0
 12  5  1  0
 20 13  1  0
 22 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  1
  7 29  1  0
 10 30  1  0
 15 31  1  0
 19 32  1  0
 22 33  1  1
 24 34  1  0
 24 35  1  0
 24 36  1  0
M  END


  Mrv1652309042216152D          

 24 27  0  0  1  0            999 V2000
   -0.4125   -0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.4934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.2211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6500    0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250    1.6500    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    1.6500    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.0789    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0625    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  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  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196211

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1OC2=C(O)C(Br)=CC3=C2C2=C1C=C(Br)C(O)=C2O[C@H]3OC

> <INCHI_IDENTIFIER>
InChI=1S/C16H12Br2O6/c1-21-15-5-3-7(17)12(20)14-9(5)10-6(16(22-2)24-14)4-8(18)11(19)13(10)23-15/h3-4,15-16,19-20H,1-2H3/t15-,16-/m1/s1

> <INCHI_KEY>
IBOLQTVCOMGQKN-HZPDHXFCSA-N

> <FORMULA>
C16H12Br2O6

> <MOLECULAR_WEIGHT>
460.074

> <EXACT_MASS>
457.900064

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
37.28940736027565

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,10R)-6,13-dibromo-3,10-dimethoxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(14),4(16),5,7,11(15),12-hexaene-7,14-diol

> <JCHEM_LOGP>
4.295762980666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.525813395739043

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.9120930020247915

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9584421326459256

> <JCHEM_POLAR_SURFACE_AREA>
77.38000000000001

> <JCHEM_REFRACTIVITY>
91.99940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,10R)-6,13-dibromo-3,10-dimethoxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(14),4(16),5,7,11(15),12-hexaene-7,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.770  -0.921   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.770  -0.921   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.540   0.413   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.080   0.413   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.850   1.746   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.390   1.746   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.160   0.413   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.160   3.080   0.000  0.00  0.00           C+0
HETATM    9 Br   UNK     0       7.700   3.080   0.000  0.00  0.00          Br+0
HETATM   10  C   UNK     0       5.390   4.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.850   4.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.540   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.770   1.746   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.770   1.746   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.540   3.080   0.000  0.00  0.00           C+0
HETATM   17 Br   UNK     0      -3.080   3.080   0.000  0.00  0.00          Br+0
HETATM   18  C   UNK     0      -0.770   4.414   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.540   5.747   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.770   4.414   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.540   5.747   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.080   5.747   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.850   7.081   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.080   8.415   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11    5   13                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13    3   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   13   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   11   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂Br₂O₆

Average Mass

460.0740 Da

Monoisotopic Mass

457.90006 Da

IUPAC Name

(3R,10R)-6,13-dibromo-3,10-dimethoxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(14),4(16),5,7,11(15),12-hexaene-7,14-diol

Traditional Name

(3R,10R)-6,13-dibromo-3,10-dimethoxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(14),4(16),5,7,11(15),12-hexaene-7,14-diol

CAS Registry Number

Not Available

SMILES

CO[C@@H]1OC2=C(O)C(Br)=CC3=C2C2=C1C=C(Br)C(O)=C2O[C@H]3OC

InChI Identifier

InChI=1S/C16H12Br2O6/c1-21-15-5-3-7(17)12(20)14-9(5)10-6(16(22-2)24-14)4-8(18)11(19)13(10)23-15/h3-4,15-16,19-20H,1-2H3/t15-,16-/m1/s1

InChI Key

IBOLQTVCOMGQKN-HZPDHXFCSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Polysiphonia stricta	LOTUS Database	35616633
Polysiphonia urceolata	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
Dibenzopyran
Benzopyran
2-benzopyran
1-benzopyran
2-bromophenol
Aryl bromide
Aryl halide
Acetal
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organohalogen compound
Organobromide
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	4.3	ChemAxon
pKa (Strongest Acidic)	7.91	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92 m³·mol⁻¹	ChemAxon
Polarizability	37.29 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

17214387

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22833196

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li K, Li XM, Ji NY, Wang BG: Bromophenols from the marine red alga Polysiphonia urceolata with DPPH radical scavenging activity. J Nat Prod. 2008 Jan;71(1):28-30. doi: 10.1021/np070281p. Epub 2007 Dec 19. [PubMed:18088100 ]
Liu QW, Tan CH, Zhang T, Zhang SJ, Han LJ, Fan X, Zhu DY: Urceolatol, a tetracyclic bromobenzaldehyde dimer from Polysiphonia urceolata. J Asian Nat Prod Res. 2006 Jun;8(4):379-83. doi: 10.1080/10286020500172269. [PubMed:16864451 ]
LOTUS database [Link]

Showing NP-Card for urceolatol (NP0196211)

MOL for NP0196211 (urceolatol)

3D MOL for NP0196211 (urceolatol)

3D SDF for NP0196211 (urceolatol)

3D-SDF for NP0196211 (urceolatol)

PDB for NP0196211 (urceolatol)

3D PDB for NP0196211 (urceolatol)

SMILES for NP0196211 (urceolatol)

INCHI for NP0196211 (urceolatol)

Structure for NP0196211 (urceolatol)

3D Structure for NP0196211 (urceolatol)