NP-MRD: Showing NP-Card for (2r,5as,7s,9as)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,7,8,9-hexahydro-1-benzoxepine (NP0328592)

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Record Information

Version

2.0

Created at

2022-09-12 12:11:55 UTC

Updated at

2022-09-12 12:11:55 UTC

NP-MRD ID

NP0328592

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,5as,7s,9as)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,7,8,9-hexahydro-1-benzoxepine

Description

Palisadin B belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups. (2r,5as,7s,9as)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,7,8,9-hexahydro-1-benzoxepine is found in Laurencia intricata and Laurencia saitoi. Based on a literature review very few articles have been published on Palisadin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
    3.4012   -1.1899    1.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2961   -0.8442    0.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3181   -1.7161   -0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1268   -1.6323   -0.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6050   -0.3446   -0.8508 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9902   -0.5399   -0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9108   -1.2464    1.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6695   -1.5384   -1.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8211    0.6871   -0.2374 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9969    0.6330    1.3303 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1223    1.9841   -0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7600    2.0284   -0.8055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1178    0.8456   -0.3372 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1705    0.9896    1.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2959    1.0292   -0.9786 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4269    0.4559   -0.5399 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2828    1.3493    0.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5309    3.0965   -0.4111 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.5052    1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3137   -2.2576    1.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3495   -1.1530    0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4581   -2.6060    0.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5693   -2.4649   -0.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4424   -1.9606   -1.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8400   -0.1165   -1.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4284   -0.7424    1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3469   -2.2890    1.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229   -1.4323    1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2856   -1.4194   -2.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7584   -1.3061   -1.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5867   -2.5687   -0.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5535    0.7005   -1.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7222    2.7633   -0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0658    2.4303    0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2787    2.9864   -0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7479    2.0263   -1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5969    2.0190    1.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7916    0.2960    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8317    1.0129    1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0875    0.2733   -1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3070    0.8860    0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086    1.3805    1.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16  2  1  0
 13  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  6
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  6
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  6
 17 41  1  0
 17 42  1  0
M  END


  Mrv1652309122214112D          

 18 19  0  0  1  0            999 V2000
    4.5529    1.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7279    1.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    1.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656    1.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    1.5316    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2062    1.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365    0.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6759    0.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    1.5316    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2228    1.1191    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062    2.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    2.3566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8590    3.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656    2.8710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    2.6874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8843    3.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5829    4.1004    0.0000 Br  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
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328592

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC[C@H]2C(C)(C)[C@@H](Br)CC[C@]2(C)O[C@H]1CBr

> <INCHI_IDENTIFIER>
InChI=1S/C15H24Br2O/c1-10-5-6-12-14(2,3)13(17)7-8-15(12,4)18-11(10)9-16/h5,11-13H,6-9H2,1-4H3/t11-,12-,13-,15-/m0/s1

> <INCHI_KEY>
BVMIPASLGLRPCO-ABHRYQDASA-N

> <FORMULA>
C15H24Br2O

> <MOLECULAR_WEIGHT>
380.164

> <EXACT_MASS>
378.019391

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.95753073964563

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,5aS,7S,9aS)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,6,7,8,9,9a-octahydro-1-benzoxepine

> <JCHEM_LOGP>
4.828415427999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.223389407280862

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
84.42219999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5aS,7S,9aS)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,7,8,9-hexahydro-1-benzoxepine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       8.499   3.629   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.959   3.629   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.291   2.242   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.789   1.899   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.585   2.859   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.251   2.089   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.241   0.909   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.262   0.909   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.918   2.859   0.000  0.00  0.00           C+0
HETATM   10 Br   UNK     0      -0.416   2.089   0.000  0.00  0.00          Br+0
HETATM   11  C   UNK     0       0.918   4.399   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.251   5.169   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.585   4.399   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.470   5.935   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.789   5.359   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.291   5.017   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.251   6.221   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0       6.688   7.654   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    2   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄Br₂O

Average Mass

380.1640 Da

Monoisotopic Mass

378.01939 Da

IUPAC Name

(2R,5aS,7S,9aS)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,6,7,8,9,9a-octahydro-1-benzoxepine

Traditional Name

(2R,5aS,7S,9aS)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,7,8,9-hexahydro-1-benzoxepine

CAS Registry Number

Not Available

SMILES

CC1=CC[C@H]2C(C)(C)[C@@H](Br)CC[C@]2(C)O[C@H]1CBr

InChI Identifier

InChI=1S/C15H24Br2O/c1-10-5-6-12-14(2,3)13(17)7-8-15(12,4)18-11(10)9-16/h5,11-13H,6-9H2,1-4H3/t11-,12-,13-,15-/m0/s1

InChI Key

BVMIPASLGLRPCO-ABHRYQDASA-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 intricata	LOTUS Database	35616633
Laurencia saitoi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Dialkyl ethers

Alternative Parents

Substituents

Oxacycle
Organoheterocyclic compound
Dialkyl ether
Hydrocarbon derivative
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	4.83	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	84.42 m³·mol⁻¹	ChemAxon
Polarizability	33.96 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

C00011561

Chemspider ID

10272762

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15241104

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,5as,7s,9as)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,7,8,9-hexahydro-1-benzoxepine (NP0328592)

MOL for NP0328592 ((2r,5as,7s,9as)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,7,8,9-hexahydro-1-benzoxepine)

3D MOL for NP0328592 ((2r,5as,7s,9as)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,7,8,9-hexahydro-1-benzoxepine)

3D SDF for NP0328592 ((2r,5as,7s,9as)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,7,8,9-hexahydro-1-benzoxepine)

3D-SDF for NP0328592 ((2r,5as,7s,9as)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,7,8,9-hexahydro-1-benzoxepine)

PDB for NP0328592 ((2r,5as,7s,9as)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,7,8,9-hexahydro-1-benzoxepine)

3D PDB for NP0328592 ((2r,5as,7s,9as)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,7,8,9-hexahydro-1-benzoxepine)

SMILES for NP0328592 ((2r,5as,7s,9as)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,7,8,9-hexahydro-1-benzoxepine)

INCHI for NP0328592 ((2r,5as,7s,9as)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,7,8,9-hexahydro-1-benzoxepine)

Structure for NP0328592 ((2r,5as,7s,9as)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,7,8,9-hexahydro-1-benzoxepine)

3D Structure for NP0328592 ((2r,5as,7s,9as)-7-bromo-2-(bromomethyl)-3,6,6,9a-tetramethyl-2,5,5a,7,8,9-hexahydro-1-benzoxepine)