NP-MRD: Showing NP-Card for 3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane (NP0216043)

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Record Information

Version

2.0

Created at

2022-09-05 15:51:29 UTC

Updated at

2022-09-05 15:51:29 UTC

NP-MRD ID

NP0216043

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane

Description

3-[Bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]Heptane belongs to the class of organic compounds known as 1,4-dioxanes. These are organic compounds containing 1,4-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 4. 3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane is found in Mycale rotalis. 3-[Bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]Heptane is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004261511222D          

 21 23  0  0  0  0            999 V2000
    0.8780    4.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8780    3.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1635    3.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1635    2.1918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5510    1.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5510    0.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    0.5418    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.1635    0.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1635   -0.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8780   -0.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6717    0.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8780    0.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925    0.5418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3069   -0.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0214   -1.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    2.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799    1.7793    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    3.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5510    3.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5510    4.2543    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
  5  6  1  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  3  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0216043

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1OC(C(Br)C2OC3CC2OC3C#C)C(Br)CC1Br

> <INCHI_IDENTIFIER>
InChI=1S/C15H19Br3O3/c1-3-9-7(16)5-8(17)14(20-9)13(18)15-12-6-11(21-15)10(4-2)19-12/h2,7-15H,3,5-6H2,1H3

> <INCHI_KEY>
OJPOYDBSPUFWBS-UHFFFAOYSA-N

> <FORMULA>
C15H19Br3O3

> <MOLECULAR_WEIGHT>
487.026

> <EXACT_MASS>
483.888433

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
37.58219987594339

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane

> <ALOGPS_LOGP>
3.78

> <JCHEM_LOGP>
3.8312154119999997

> <ALOGPS_LOGS>
-4.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.753857777120531

> <JCHEM_POLAR_SURFACE_AREA>
27.69

> <JCHEM_REFRACTIVITY>
89.78829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane

> <JCHEM_VEBER_RULE>
1

$$$$

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       1.639   7.941   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.639   6.401   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.305   5.631   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.305   4.091   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.028   3.321   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.028   1.781   0.000  0.00  0.00           C+0
HETATM    7 Br   UNK     0      -2.362   1.011   0.000  0.00  0.00          Br+0
HETATM    8  C   UNK     0       0.305   1.011   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.305  -0.529   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.639  -1.299   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.254   0.241   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.639   1.781   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.973   1.011   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.973  -0.529   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.306  -1.299   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.640  -2.069   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.362   4.091   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0      -3.696   3.321   0.000  0.00  0.00          Br+0
HETATM   19  C   UNK     0      -2.362   5.631   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.028   6.401   0.000  0.00  0.00           C+0
HETATM   21 Br   UNK     0      -1.028   7.941   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    8   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17    5   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    3   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₉Br₃O₃

Average Mass

487.0260 Da

Monoisotopic Mass

483.88843 Da

IUPAC Name

3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane

Traditional Name

3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane

CAS Registry Number

Not Available

SMILES

CCC1OC(C(Br)C2OC3CC2OC3C#C)C(Br)CC1Br

InChI Identifier

InChI=1S/C15H19Br3O3/c1-3-9-7(16)5-8(17)14(20-9)13(18)15-12-6-11(21-15)10(4-2)19-12/h2,7-15H,3,5-6H2,1H3

InChI Key

OJPOYDBSPUFWBS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mycale rotalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,4-dioxanes. These are organic compounds containing 1,4-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 4.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dioxanes

Sub Class

1,4-dioxanes

Direct Parent

1,4-dioxanes

Alternative Parents

Substituents

Oxane
Para-dioxane
Tetrahydrofuran
Acetylide
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organobromide
Organohalogen compound
Alkyl halide
Alkyl bromide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.78	ALOGPS
logP	3.83	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.79 m³·mol⁻¹	ChemAxon
Polarizability	37.58 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

14777632

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane (NP0216043)

MOL for NP0216043 (3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane)

3D MOL for NP0216043 (3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane)

3D SDF for NP0216043 (3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane)

3D-SDF for NP0216043 (3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane)

PDB for NP0216043 (3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane)

3D PDB for NP0216043 (3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane)

SMILES for NP0216043 (3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane)

INCHI for NP0216043 (3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane)

Structure for NP0216043 (3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane)

3D Structure for NP0216043 (3-[bromo(3,5-dibromo-6-ethyloxan-2-yl)methyl]-6-ethynyl-2,5-dioxabicyclo[2.2.1]heptane)