NP-MRD: Showing NP-Card for 2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane (NP0155051)

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Record Information

Version

2.0

Created at

2022-09-02 12:03:09 UTC

Updated at

2022-09-02 12:03:09 UTC

NP-MRD ID

NP0155051

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane

Description

2-(Bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]Octane belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. 2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane is found in Laurencia dendroidea. 2-(Bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]Octane is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    4.8955    0.7751   -1.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8740   -0.1939   -1.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8600   -1.3348   -0.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8540   -1.5720    0.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7074   -0.6377    0.6573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4119   -1.3232    0.2816 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0892   -2.5965    1.4947 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2935   -0.3252    0.3172 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4961    0.7149   -0.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3848    2.0308   -0.1017 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4694    3.0302   -0.4061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8688    2.0164    0.6412 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0225    1.2458    0.0977 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2550    1.8399    0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2827    3.7717    0.5245 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0393   -0.2180    0.3464 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1179   -0.7934   -0.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2933   -2.2758   -0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102   -0.9226    0.0445 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9172    1.6215   -2.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6983   -2.0080   -0.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8716   -2.4402    1.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5993   -0.3260    1.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9488    0.2183    0.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5079   -1.7407   -0.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2710    0.1080    1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4809    0.6160   -1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2435    0.5839   -1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2884    2.3144    0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9332    2.4779    1.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2404    1.4088   -0.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2064    1.6729    1.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1966    1.4697    0.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4290   -0.4046    1.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0883   -0.3038   -0.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8142   -0.6715   -1.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002   -2.5877   -0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4203   -2.4451    0.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4185   -2.7956   -0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  1  0
 16 19  1  0
 19  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  8  6  1  0
  6  7  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  3  0
 13 16  1  0
 12 10  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 17 35  1  0
 17 36  1  0
 16 34  1  1
  8 26  1  1
  9 27  1  0
  9 28  1  0
 10 29  1  1
 12 30  1  1
 13 31  1  6
 14 32  1  0
 14 33  1  0
  6 25  1  6
  5 23  1  0
  5 24  1  0
  4 22  1  0
  3 21  1  0
  1 20  1  0
M  END


  Mrv1533004191523492D          

 19 20  0  0  0  0            999 V2000
    3.7433    3.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0447    2.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    1.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8883    0.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304    0.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7260   -0.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810    0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3666    0.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810    1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7260    1.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5425    2.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7541    2.8618    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.0447   -0.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8605   -0.3779    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7433   -1.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2577   -1.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9563   -2.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4707   -3.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9851   -3.9718    0.0000 C   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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 16 15  1  4  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  3  0  0  0  0
M  END
> <DATABASE_ID>
NP0155051

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1OC(CC2OC2C1CBr)C(Cl)CC=CC#C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20BrClO2/c1-3-5-6-7-11(17)13-8-14-15(19-14)10(9-16)12(4-2)18-13/h1,5-6,10-15H,4,7-9H2,2H3

> <INCHI_KEY>
WWXDSNUMWFIGFH-UHFFFAOYSA-N

> <FORMULA>
C15H20BrClO2

> <MOLECULAR_WEIGHT>
347.68

> <EXACT_MASS>
346.033521

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
33.04587142611416

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane

> <ALOGPS_LOGP>
4.10

> <JCHEM_LOGP>
3.5848701983333333

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.891943388450343

> <JCHEM_POLAR_SURFACE_AREA>
21.759999999999998

> <JCHEM_REFRACTIVITY>
81.48830000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.29e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane

> <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       6.988   5.682   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.550   4.248   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.590   3.044   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.258   1.657   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.590   0.269   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.089  -0.074   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.885   0.887   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.551   1.657   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.885   2.427   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.089   3.387   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.746   4.888   0.000  0.00  0.00           C+0
HETATM   12 Br   UNK     0       3.274   5.342   0.000  0.00  0.00          Br+0
HETATM   13  C   UNK     0       7.550  -0.935   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       9.073  -0.705   0.000  0.00  0.00          Cl+0
HETATM   15  C   UNK     0       6.988  -2.368   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.948  -3.572   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.385  -5.006   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.345  -6.210   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.305  -7.414   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    9                                                       
CONECT    9    8    7   10                                                  
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀BrClO₂

Average Mass

347.6800 Da

Monoisotopic Mass

346.03352 Da

IUPAC Name

2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane

Traditional Name

2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane

CAS Registry Number

Not Available

SMILES

CCC1OC(CC2OC2C1CBr)C(Cl)CC=CC#C

InChI Identifier

InChI=1S/C15H20BrClO2/c1-3-5-6-7-11(17)13-8-14-15(19-14)10(9-16)12(4-2)18-13/h1,5-6,10-15H,4,7-9H2,2H3

InChI Key

WWXDSNUMWFIGFH-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
Laurencia dendroidea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Dialkyl ether
Oxirane
Ether
Oxacycle
Acetylide
Organochloride
Organobromide
Organohalogen compound
Alkyl chloride
Alkyl bromide
Organooxygen compound
Organic oxygen compound
Alkyl halide
Hydrocarbon derivative
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	4.1	ALOGPS
logP	3.58	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	21.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	81.49 m³·mol⁻¹	ChemAxon
Polarizability	33.05 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

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

73799555

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane (NP0155051)

MOL for NP0155051 (2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane)

3D MOL for NP0155051 (2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane)

3D SDF for NP0155051 (2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane)

3D-SDF for NP0155051 (2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane)

PDB for NP0155051 (2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane)

3D PDB for NP0155051 (2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane)

SMILES for NP0155051 (2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane)

INCHI for NP0155051 (2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane)

Structure for NP0155051 (2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane)

3D Structure for NP0155051 (2-(bromomethyl)-5-(1-chlorohex-3-en-5-yn-1-yl)-3-ethyl-4,8-dioxabicyclo[5.1.0]octane)