NP-MRD: Showing NP-Card for n-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)ethanimidic acid (NP0284635)

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Record Information

Version

2.0

Created at

2022-09-09 12:26:22 UTC

Updated at

2022-09-09 12:26:22 UTC

NP-MRD ID

NP0284635

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)ethanimidic acid

Description

4-Acetamido-2,6-dibromo-4-hydroxy-1,1-dimethoxycyclohexa-2,5-diene belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. n-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)ethanimidic acid is found in Pseudoceratina purpurea. 4-Acetamido-2,6-dibromo-4-hydroxy-1,1-dimethoxycyclohexa-2,5-diene is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.8122    1.4520    0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7704    0.7910    0.9948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6160    0.6069    0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8618   -0.1138   -0.9112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3867   -1.3571   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7979    1.8006    0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4075    3.5976    0.0269 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.4961    1.6123   -0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0205    0.2179   -0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6721   -0.3727   -1.5097 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619    0.2086   -0.1680 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1641   -1.0206   -0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6447   -1.0093   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5485   -2.1364   -0.2776 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4483   -0.5728    0.7990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8092   -0.3889    1.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6732   -1.3289    2.4915 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5960    2.4730    0.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6198    1.4966    1.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2221    0.8465   -0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3322   -1.3104   -0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6199   -1.9203   -0.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5598   -1.8923   -1.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0984    2.4753   -0.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3643   -0.9308   -1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9898    1.0860   -0.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8934   -0.8584    1.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1086   -1.9734   -0.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1044   -0.2173   -0.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0696   -1.2608    1.3212 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
  3  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  9 15  1  0
 15 16  2  0
 16 17  1  0
 16  3  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  5 22  1  0
  5 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 15 30  1  0
M  END


  Mrv1533004261501352D          

 17 17  0  0  0  0            999 V2000
    0.9626    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -1.0445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283   -0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586   -1.5332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105   -0.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 Br  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  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
  6 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0284635

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1(OC)C(Br)=CC(O)(NC(C)=O)C=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C10H13Br2NO4/c1-6(14)13-9(15)4-7(11)10(16-2,17-3)8(12)5-9/h4-5,15H,1-3H3,(H,13,14)

> <INCHI_KEY>
GFMBTVWUKRAEFD-UHFFFAOYSA-N

> <FORMULA>
C10H13Br2NO4

> <MOLECULAR_WEIGHT>
371.025

> <EXACT_MASS>
368.921134

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
27.60383413032917

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)acetamide

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
1.2155532889999998

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.897744888943874

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.879683377712487

> <JCHEM_PKA_STRONGEST_BASIC>
-2.045965500656773

> <JCHEM_POLAR_SURFACE_AREA>
67.78999999999999

> <JCHEM_REFRACTIVITY>
71.16890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       1.797   4.937   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.324   3.490   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.344   3.490   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.870   4.937   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.324  -1.950   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       0.344  -1.950   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -1.173  -1.682   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.163  -2.862   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.700  -0.235   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0      -1.334   2.310   0.000  0.00  0.00          Br+0
HETATM   17 Br   UNK     0       4.001   2.310   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6   15                                             
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   14                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15                                                       
CONECT   15   14    3   16                                                  
CONECT   16   15                                                            
CONECT   17    6                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
N-(3,5-Dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)ethanimidate	Generator

Chemical Formula

C₁₀H₁₃Br₂NO₄

Average Mass

371.0250 Da

Monoisotopic Mass

368.92113 Da

IUPAC Name

N-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)acetamide

Traditional Name

N-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)acetamide

CAS Registry Number

Not Available

SMILES

COC1(OC)C(Br)=CC(O)(NC(C)=O)C=C1Br

InChI Identifier

InChI=1S/C10H13Br2NO4/c1-6(14)13-9(15)4-7(11)10(16-2,17-3)8(12)5-9/h4-5,15H,1-3H3,(H,13,14)

InChI Key

GFMBTVWUKRAEFD-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, 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
Pseudoceratina purpurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Alkanolamine
Carboximidic acid
Carboximidic acid derivative
Vinyl bromide
Vinyl halide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Bromoalkene
Haloalkene
Organobromide
Organonitrogen compound
Organohalogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	1.08	ALOGPS
logP	1.22	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	10.88	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.79 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.17 m³·mol⁻¹	ChemAxon
Polarizability	27.6 Å³	ChemAxon
Number of Rings	1	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

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

129881759

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)ethanimidic acid (NP0284635)

MOL for NP0284635 (n-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)ethanimidic acid)

3D MOL for NP0284635 (n-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)ethanimidic acid)

3D SDF for NP0284635 (n-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)ethanimidic acid)

3D-SDF for NP0284635 (n-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)ethanimidic acid)

PDB for NP0284635 (n-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)ethanimidic acid)

3D PDB for NP0284635 (n-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)ethanimidic acid)

SMILES for NP0284635 (n-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)ethanimidic acid)

INCHI for NP0284635 (n-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)ethanimidic acid)

Structure for NP0284635 (n-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)ethanimidic acid)

3D Structure for NP0284635 (n-(3,5-dibromo-1-hydroxy-4,4-dimethoxycyclohexa-2,5-dien-1-yl)ethanimidic acid)