NP-MRD: Showing NP-Card for (5r)-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methylfuran-2-one (NP0190992)

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Record Information

Version

2.0

Created at

2022-09-04 07:46:57 UTC

Updated at

2022-09-04 07:46:57 UTC

NP-MRD ID

NP0190992

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r)-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methylfuran-2-one

Description

(5R)-5-[(1S,3S,4S)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methyl-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as cyclohexyl halides. These are organohalogen compounds containing a monocyclic cyclohexane moiety that is substituted at one or more positions by an halogen atom. (5r)-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methylfuran-2-one is found in Osmundea hybrida. Based on a literature review very few articles have been published on (5R)-5-[(1S,3S,4S)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methyl-2,5-dihydrofuran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
    3.8160   -0.2061   -0.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671    0.0360    0.0993 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6137    0.3886    1.8560 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6290   -1.2264   -0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2932   -1.0407    0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3815    0.2508    0.3024 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8110   -0.0644   -0.0822 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8595   -1.0096   -1.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5843    1.1169   -0.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6597    1.1936    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6413    0.0476    1.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5431   -0.1981    2.0796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139   -0.6923    0.9451 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3087    0.8514   -0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7599    1.1630   -0.5953 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6176    1.4931   -2.3153 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.8027   -1.0375   -1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1716    0.7391   -0.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5953   -0.4459    0.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1899   -2.0220    0.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4678   -1.5261   -1.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180   -1.9388    0.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4762   -1.0627    1.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3885    0.9348    1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7014   -1.7252   -1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8970   -1.4936   -1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0948   -0.4174   -2.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3897    1.8846   -1.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4433    1.9796    0.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.1385   -1.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1663    1.8153   -1.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8930    2.0740    0.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  6
  7 13  1  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  9  2  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  1
  2 15  1  0
 15 16  1  0
 15 14  1  0
  9  7  1  0
 14  6  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
 10 29  1  0
  9 28  1  0
  6 24  1  1
  5 22  1  0
  5 23  1  0
  4 20  1  0
  4 21  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
 15 32  1  1
 14 30  1  0
 14 31  1  0
M  END


  Mrv1652309042209462D          

 16 17  0  0  1  0            999 V2000
    2.7180    5.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9010    5.1251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9298    5.9496    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1559    4.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6039    3.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7969    3.8989    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2449    3.2858    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3071    3.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9123    2.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6574    2.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676    2.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6525    1.3488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4226    2.8009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5420    4.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0940    5.2966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8391    6.0812    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  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
  7 13  1  6  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0190992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1(OC(=O)C=C1)[C@H]1CC[C@](C)(Cl)[C@@H](Br)C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H16BrClO2/c1-11(14)5-3-8(7-9(11)13)12(2)6-4-10(15)16-12/h4,6,8-9H,3,5,7H2,1-2H3/t8-,9-,11-,12-/m0/s1

> <INCHI_KEY>
ASFOVSPTTGYDMB-QSFUFRPTSA-N

> <FORMULA>
C12H16BrClO2

> <MOLECULAR_WEIGHT>
307.61

> <EXACT_MASS>
306.00222

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.13094566655166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R)-5-[(1S,3S,4S)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methyl-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
3.704876104333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.828395332771367

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
68.0555

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-5-[(1S,3S,4S)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methylfuran-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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       5.074   9.781   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.548   9.567   0.000  0.00  0.00           C+0
HETATM    3 Cl   UNK     0       3.602  11.106   0.000  0.00  0.00          Cl+0
HETATM    4  C   UNK     0       4.024   8.102   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.994   6.958   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.488   7.278   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.457   6.134   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.573   7.278   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.703   5.228   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.227   3.764   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.313   3.764   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.218   2.518   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.789   5.228   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.012   8.743   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.042   9.887   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0       1.566  11.352   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3    4   15                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8    9   13                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7                                                       
CONECT   14    6   15                                                       
CONECT   15   14    2   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₆BrClO₂

Average Mass

307.6100 Da

Monoisotopic Mass

306.00222 Da

IUPAC Name

(5R)-5-[(1S,3S,4S)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

(5R)-5-[(1S,3S,4S)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methylfuran-2-one

CAS Registry Number

Not Available

SMILES

C[C@@]1(OC(=O)C=C1)[C@H]1CC[C@](C)(Cl)[C@@H](Br)C1

InChI Identifier

InChI=1S/C12H16BrClO2/c1-11(14)5-3-8(7-9(11)13)12(2)6-4-10(15)16-12/h4,6,8-9H,3,5,7H2,1-2H3/t8-,9-,11-,12-/m0/s1

InChI Key

ASFOVSPTTGYDMB-QSFUFRPTSA-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
Osmundea hybrida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexyl halides. These are organohalogen compounds containing a monocyclic cyclohexane moiety that is substituted at one or more positions by an halogen atom.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Alkyl halides

Sub Class

Cyclohexyl halides

Direct Parent

Cyclohexyl halides

Alternative Parents

Substituents

Cyclohexyl halide
2-furanone
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Alkyl chloride
Alkyl bromide
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organobromide
Organochloride
Organooxygen compound
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	3.7	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.06 m³·mol⁻¹	ChemAxon
Polarizability	27.13 Å³	ChemAxon
Number of Rings	2	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

29216062

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162977827

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5r)-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methylfuran-2-one (NP0190992)

MOL for NP0190992 ((5r)-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methylfuran-2-one)

3D MOL for NP0190992 ((5r)-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methylfuran-2-one)

3D SDF for NP0190992 ((5r)-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methylfuran-2-one)

3D-SDF for NP0190992 ((5r)-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methylfuran-2-one)

PDB for NP0190992 ((5r)-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methylfuran-2-one)

3D PDB for NP0190992 ((5r)-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methylfuran-2-one)

SMILES for NP0190992 ((5r)-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methylfuran-2-one)

INCHI for NP0190992 ((5r)-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methylfuran-2-one)

Structure for NP0190992 ((5r)-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methylfuran-2-one)

3D Structure for NP0190992 ((5r)-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-5-methylfuran-2-one)