NP-MRD: Showing NP-Card for 9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene (NP0214427)

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Record Information

Version

2.0

Created at

2022-09-05 13:43:32 UTC

Updated at

2022-09-05 13:43:32 UTC

NP-MRD ID

NP0214427

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene

Description

9-Bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]Tridec-6-ene belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. 9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene is found in Laurencia dendroidea and Laurencia obtusa. 9-Bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]Tridec-6-ene 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
    2.2571   -2.4121   -0.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602   -1.9252   -0.0263 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1332   -2.9131   -0.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4142   -2.6460   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0618   -1.7958    0.8564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0082   -0.7708    0.2176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0862   -0.0456    1.6464 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1217    0.3361   -0.3031 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8156    1.6750   -0.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6214    2.6157   -0.1230 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1217    3.2888   -1.6965 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5566    1.7418    0.4551 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6767    1.6487   -0.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3746    0.3479   -0.0322 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7671    0.4571   -0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5376    1.1630    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1973    2.0046    1.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0900    3.8113    0.6590 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.6840   -0.6948   -0.6087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0524    0.4571    0.5589 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2892   -2.0775   -1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2240   -3.5278   -0.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1348   -2.0554   -0.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1615   -1.7551    1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1732   -3.9265   -0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0779   -3.0714   -0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272   -2.4644    1.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3511   -1.2976    1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6138   -1.2427   -0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8519    0.0770   -1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5240    1.7775    0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2600    1.8545   -1.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8869    3.3878    0.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2307    2.0506    1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3623    1.5948   -1.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3287    2.5185   -0.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3255    0.2221    1.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2733    0.0658   -1.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993    1.5262    1.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 19  1  0
 19 14  1  0
 14 13  1  0
 13 12  1  0
 12 20  1  0
 20  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  8  6  1  0
  6  7  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
 14 15  1  0
 15 16  2  0
 16 17  2  0
 17 18  1  0
  3  2  1  0
 10 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
 14 37  1  1
 13 35  1  0
 13 36  1  0
 12 34  1  1
  8 30  1  6
  9 31  1  0
  9 32  1  0
 10 33  1  1
  6 29  1  6
  5 27  1  0
  5 28  1  0
  4 26  1  0
  3 25  1  0
 15 38  1  0
 17 39  1  0
M  END


  Mrv1533004231519342D          

 20 21  0  0  0  0            999 V2000
    5.0221    0.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2157    0.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6617    0.3007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7718    0.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560    0.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4447    0.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7827    1.3491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5440    2.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7275    1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771    0.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0187    0.4557    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0980    2.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8456    3.6166    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.9044    2.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569    1.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9633    1.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9159   -0.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6915   -0.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4670   -0.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0985   -0.3912    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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
  2 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0214427

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(CC2OC(CC2Cl)C(Br)CC=C1)C=C=CBr

> <INCHI_IDENTIFIER>
InChI=1S/C15H19Br2ClO2/c1-10-4-2-6-12(17)14-9-13(18)15(20-14)8-11(19-10)5-3-7-16/h2,4-5,7,10-15H,6,8-9H2,1H3

> <INCHI_KEY>
OHWBWBOWCXAQRI-UHFFFAOYSA-N

> <FORMULA>
C15H19Br2ClO2

> <MOLECULAR_WEIGHT>
426.57

> <EXACT_MASS>
423.944034

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
35.55326120429639

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene

> <ALOGPS_LOGP>
5.09

> <JCHEM_LOGP>
4.350283018333332

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9034575318532325

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
90.42630000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.32e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       9.375   1.378   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.869   1.703   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.835   0.561   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.174   0.845   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.838   0.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.697   1.114   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.328   2.518   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.882   4.144   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.358   3.215   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.264   1.678   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0      -0.035   0.851   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       3.916   5.285   0.000  0.00  0.00           C+0
HETATM   13 Br   UNK     0       3.445   6.751   0.000  0.00  0.00          Br+0
HETATM   14  C   UNK     0       5.422   4.960   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.893   3.494   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.398   3.169   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.443  -0.671   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.891  -1.196   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.338  -1.721   0.000  0.00  0.00           C+0
HETATM   20 Br   UNK     0       9.517  -0.730   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    2                                                       
CONECT   17    4   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₉Br₂ClO₂

Average Mass

426.5700 Da

Monoisotopic Mass

423.94403 Da

IUPAC Name

9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene

Traditional Name

9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene

CAS Registry Number

Not Available

SMILES

CC1OC(CC2OC(CC2Cl)C(Br)CC=C1)C=C=CBr

InChI Identifier

InChI=1S/C15H19Br2ClO2/c1-10-4-2-6-12(17)14-9-13(18)15(20-14)8-11(19-10)5-3-7-16/h2,4-5,7,10-15H,6,8-9H2,1H3

InChI Key

OHWBWBOWCXAQRI-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
Laurencia obtusa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Substituents

Tetrahydrofuran
Dialkyl ether
Ether
Vinyl bromide
Vinyl halide
Oxacycle
Organooxygen compound
Organochloride
Organobromide
Organohalogen compound
Alkyl bromide
Organic oxygen compound
Alkyl chloride
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	5.09	ALOGPS
logP	4.35	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	90.43 m³·mol⁻¹	ChemAxon
Polarizability	35.55 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

72739457

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene (NP0214427)

MOL for NP0214427 (9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene)

3D MOL for NP0214427 (9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene)

3D SDF for NP0214427 (9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene)

3D-SDF for NP0214427 (9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene)

PDB for NP0214427 (9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene)

3D PDB for NP0214427 (9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene)

SMILES for NP0214427 (9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene)

INCHI for NP0214427 (9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene)

Structure for NP0214427 (9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene)

3D Structure for NP0214427 (9-bromo-3-(3-bromopropa-1,2-dien-1-yl)-12-chloro-5-methyl-4,13-dioxabicyclo[8.2.1]tridec-6-ene)