NP-MRD: Showing NP-Card for 5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate (NP0256343)

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Record Information

Version

2.0

Created at

2022-09-07 21:08:17 UTC

Updated at

2022-09-07 21:08:17 UTC

NP-MRD ID

NP0256343

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate

Description

5-Acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate 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. 5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate is found in Osmundea hybrida. Based on a literature review very few articles have been published on 5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072223082D          

 23 24  0  0  0  0            999 V2000
    3.5923   -0.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8076   -0.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1946    0.0718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6361   -1.2872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8515   -1.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -2.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7716   -2.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8578   -3.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1904   -3.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115   -3.4828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0354   -2.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2904   -3.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0973   -3.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6494   -2.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1573   -3.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3778   -2.4541    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3944   -2.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9465   -1.4437    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5874   -1.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5166   -1.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1841   -1.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7791   -0.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5891   -0.3385    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256343

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC(OC1(C)C)(C1CCC(C)(Cl)C(Br)C1)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H26BrClO4/c1-10(20)17(12-6-7-16(5,19)13(18)8-12)9-14(22-11(2)21)15(3,4)23-17/h12-14H,6-9H2,1-5H3

> <INCHI_KEY>
AICKVNLPJQIZBB-UHFFFAOYSA-N

> <FORMULA>
C17H26BrClO4

> <MOLECULAR_WEIGHT>
409.75

> <EXACT_MASS>
408.0703

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
38.385548234398655

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate

> <JCHEM_LOGP>
3.4443662193333315

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.948172156793866

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2783348414107

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
91.92530000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       6.706  -0.421   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.241  -0.896   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.096   0.134   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.921  -2.403   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.456  -2.879   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.980  -4.343   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.440  -4.343   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.601  -5.875   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.355  -6.780   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.008  -6.501   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.066  -4.664   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.542  -6.128   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.048  -6.448   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.079  -5.304   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.027  -6.517   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0      -4.439  -4.581   0.000  0.00  0.00          Cl+0
HETATM   17  C   UNK     0      -2.603  -3.839   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0      -3.633  -2.695   0.000  0.00  0.00          Br+0
HETATM   19  C   UNK     0      -1.097  -3.519   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.964  -2.879   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.210  -1.974   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.454  -0.632   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.966  -0.632   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11   20                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11                                                       
CONECT   20    7   21                                                       
CONECT   21   20    5   22   23                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
5-Acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₆BrClO₄

Average Mass

409.7500 Da

Monoisotopic Mass

408.07030 Da

IUPAC Name

5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate

Traditional Name

5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC(OC1(C)C)(C1CCC(C)(Cl)C(Br)C1)C(C)=O

InChI Identifier

InChI=1S/C17H26BrClO4/c1-10(20)17(12-6-7-16(5,19)13(18)8-12)9-14(22-11(2)21)15(3,4)23-17/h12-14H,6-9H2,1-5H3

InChI Key

AICKVNLPJQIZBB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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
Tetrahydrofuran
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organic oxide
Alkyl chloride
Alkyl bromide
Organobromide
Organochloride
Organooxygen compound
Hydrocarbon derivative
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	3.44	ChemAxon
pKa (Strongest Acidic)	17.95	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.93 m³·mol⁻¹	ChemAxon
Polarizability	38.39 Å³	ChemAxon
Number of Rings	2	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

14314406

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate (NP0256343)

MOL for NP0256343 (5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate)

3D MOL for NP0256343 (5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate)

3D SDF for NP0256343 (5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate)

3D-SDF for NP0256343 (5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate)

PDB for NP0256343 (5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate)

3D PDB for NP0256343 (5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate)

SMILES for NP0256343 (5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate)

INCHI for NP0256343 (5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate)

Structure for NP0256343 (5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate)

3D Structure for NP0256343 (5-acetyl-5-(3-bromo-4-chloro-4-methylcyclohexyl)-2,2-dimethyloxolan-3-yl acetate)