NP-MRD: Showing NP-Card for 8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal (NP0321366)

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Record Information

Version

2.0

Created at

2022-09-11 23:32:25 UTC

Updated at

2022-09-11 23:32:25 UTC

NP-MRD ID

NP0321366

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal

Description

8-Bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position. 8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal is found in Plocamium cartilagineum. 8-Bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191514282D          

 15 14  0  0  0  0            999 V2000
    3.3000    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.6039    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625    0.7145    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    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
   -0.4125   -0.7145    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  4  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  7  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  4  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0321366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(Cl)(C=CBr)C(Cl)C=CC(=CCl)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10BrCl3O/c1-10(14,4-5-11)9(13)3-2-8(6-12)7-15/h2-7,9H,1H3

> <INCHI_KEY>
GKZINEHWKIQNIO-UHFFFAOYSA-N

> <FORMULA>
C10H10BrCl3O

> <MOLECULAR_WEIGHT>
332.44

> <EXACT_MASS>
329.898061

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
26.70662086362565

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal

> <ALOGPS_LOGP>
4.57

> <JCHEM_LOGP>
3.965871381

> <ALOGPS_LOGS>
-5.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.403573150795769

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
70.77319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.74e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       6.160   4.207   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    3 Cl   UNK     0       6.160   1.127   0.000  0.00  0.00          Cl+0
HETATM    4  C   UNK     0       7.700   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.470   1.334   0.000  0.00  0.00           C+0
HETATM    6 Br   UNK     0      10.010   1.334   0.000  0.00  0.00          Br+0
HETATM    7  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       3.850   4.001   0.000  0.00  0.00          Cl+0
HETATM    9  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      -0.770  -1.334   0.000  0.00  0.00          Cl+0
HETATM   14  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    7                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    2    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₀BrCl₃O

Average Mass

332.4400 Da

Monoisotopic Mass

329.89806 Da

IUPAC Name

8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal

Traditional Name

8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal

CAS Registry Number

Not Available

SMILES

CC(Cl)(C=CBr)C(Cl)C=CC(=CCl)C=O

InChI Identifier

InChI=1S/C10H10BrCl3O/c1-10(14,4-5-11)9(13)3-2-8(6-12)7-15/h2-7,9H,1H3

InChI Key

GKZINEHWKIQNIO-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
Plocamium cartilagineum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enals

Alternative Parents

Substituents

Enal
Vinylogous halide
Vinyl bromide
Vinyl chloride
Vinyl halide
Haloalkene
Bromoalkene
Chloroalkene
Aldehyde
Organochloride
Organobromide
Alkyl chloride
Hydrocarbon derivative
Alkyl halide
Organic oxide
Organohalogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	4.57	ALOGPS
logP	3.97	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	70.77 m³·mol⁻¹	ChemAxon
Polarizability	26.71 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

53843851

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal (NP0321366)

MOL for NP0321366 (8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal)

3D MOL for NP0321366 (8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal)

3D SDF for NP0321366 (8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal)

3D-SDF for NP0321366 (8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal)

PDB for NP0321366 (8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal)

3D PDB for NP0321366 (8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal)

SMILES for NP0321366 (8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal)

INCHI for NP0321366 (8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal)

Structure for NP0321366 (8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal)

3D Structure for NP0321366 (8-bromo-5,6-dichloro-2-(chloromethylidene)-6-methylocta-3,7-dienal)