NP-MRD: Showing NP-Card for (2s,5r,7s,8s)-7-bromo-8-chloro-8-methyl-4-methylidene-2-(2-methylprop-1-en-1-yl)-1-oxaspiro[4.5]decane (NP0241112)

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Record Information

Version

2.0

Created at

2022-09-07 01:06:01 UTC

Updated at

2022-09-07 01:06:02 UTC

NP-MRD ID

NP0241112

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,5r,7s,8s)-7-bromo-8-chloro-8-methyl-4-methylidene-2-(2-methylprop-1-en-1-yl)-1-oxaspiro[4.5]decane

Description

(2S,5R,7S,8S)-2-(2-Methyl-1-propenyl)-4-methylene-7-bromo-8-chloro-8-methyl-1-oxaspiro[4.5]Decane belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units. (2s,5r,7s,8s)-7-bromo-8-chloro-8-methyl-4-methylidene-2-(2-methylprop-1-en-1-yl)-1-oxaspiro[4.5]decane is found in Laurencia saitoi. Based on a literature review very few articles have been published on (2S,5R,7S,8S)-2-(2-Methyl-1-propenyl)-4-methylene-7-bromo-8-chloro-8-methyl-1-oxaspiro[4.5]Decane.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    0.6621   -1.6387   -2.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0180   -0.8527   -1.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4494   -0.7560   -1.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5736    0.6377   -0.5094 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4405    0.7481    0.6857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7142    0.4345    0.6847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3697   -0.0676   -0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5433    0.5632    1.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3378    1.1769   -0.2980 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6148    0.1783   -0.4231 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8977   -0.4989    0.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3304   -0.9776    0.8799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2951    0.1948    1.0099 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6856   -0.2018    0.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4380    0.7195    2.7042 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7446    1.3369    0.1878 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2072    2.2969   -0.6057 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.8617    0.8059   -0.9503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7331   -1.5861   -2.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1280   -2.3571   -2.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9639   -0.9305   -1.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6922   -1.5325   -0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0565    1.2445   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9839    1.1082    1.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4835   -0.0028   -0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1050    0.5921   -1.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250   -1.1231   -0.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9424    1.6007    1.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8902    0.4646    2.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3739   -0.1685    1.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7781    0.1833    1.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2407   -1.3905    1.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5914   -1.5767    0.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5022   -1.6042    1.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0473   -0.9555    1.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6577   -0.6583   -0.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3270    0.6774    0.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1782    2.0085    0.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6200    1.7251   -1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4863    0.1822   -1.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  6  5  2  3
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  1
 13 16  1  0
 16 17  1  0
 16 18  1  0
 10  9  1  1
  9  4  1  0
 18 10  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  5 24  1  0
  4 23  1  6
  3 21  1  0
  3 22  1  0
  1 19  1  0
  1 20  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  1
 18 39  1  0
 18 40  1  0
M  END


  Mrv1652309072203062D          

 18 19  0  0  1  0            999 V2000
    1.0396   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6674    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5812    2.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2486    2.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1725    2.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6820    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9195    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5515    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5515   -0.1178    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9195   -1.0164    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.6820   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
 10  9  1  6  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 10 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0241112

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C[C@@H]1CC(=C)[C@]2(CC[C@](C)(Cl)[C@@H](Br)C2)O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22BrClO/c1-10(2)7-12-8-11(3)15(18-12)6-5-14(4,17)13(16)9-15/h7,12-13H,3,5-6,8-9H2,1-2,4H3/t12-,13+,14+,15-/m1/s1

> <INCHI_KEY>
ABDRCZBRWYOHQL-CBBWQLFWSA-N

> <FORMULA>
C15H22BrClO

> <MOLECULAR_WEIGHT>
333.69

> <EXACT_MASS>
332.054256

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.64312246757899

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,5R,7S,8S)-7-bromo-8-chloro-8-methyl-4-methylidene-2-(2-methylprop-1-en-1-yl)-1-oxaspiro[4.5]decane

> <JCHEM_LOGP>
4.4105195550000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.247416184951773

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
81.12889999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5R,7S,8S)-7-bromo-8-chloro-8-methyl-4-methylidene-2-(2-methylprop-1-en-1-yl)-1-oxaspiro[4.5]decane

> <JCHEM_VEBER_RULE>
1

$$$$

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       1.941  -1.941   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.246   2.445   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.085   3.977   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.331   4.882   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.322   4.603   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.465   2.016   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.140   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.680   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.450   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.630   1.760   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0       6.630  -0.220   0.000  0.00  0.00          Cl+0
HETATM   16  C   UNK     0       4.680  -0.564   0.000  0.00  0.00           C+0
HETATM   17 Br   UNK     0       5.450  -1.897   0.000  0.00  0.00          Br+0
HETATM   18  C   UNK     0       3.140  -0.564   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10                                                       
CONECT   10    9    2   11   18                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   10                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂BrClO

Average Mass

333.6900 Da

Monoisotopic Mass

332.05426 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)=C[C@@H]1CC(=C)[C@]2(CC[C@](C)(Cl)[C@@H](Br)C2)O1

InChI Identifier

InChI=1S/C15H22BrClO/c1-10(2)7-12-8-11(3)15(18-12)6-5-14(4,17)13(16)9-15/h7,12-13H,3,5-6,8-9H2,1-2,4H3/t12-,13+,14+,15-/m1/s1

InChI Key

ABDRCZBRWYOHQL-CBBWQLFWSA-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 saitoi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monoterpenoids

Alternative Parents

Substituents

Monoterpenoid
Tetrahydrofuran
Dialkyl ether
Ether
Organoheterocyclic compound
Oxacycle
Organochloride
Organobromide
Organohalogen compound
Organic oxygen compound
Alkyl bromide
Organooxygen compound
Hydrocarbon derivative
Alkyl chloride
Alkyl halide
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

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

27024263

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102482902

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,5r,7s,8s)-7-bromo-8-chloro-8-methyl-4-methylidene-2-(2-methylprop-1-en-1-yl)-1-oxaspiro[4.5]decane (NP0241112)

MOL for NP0241112 ((2s,5r,7s,8s)-7-bromo-8-chloro-8-methyl-4-methylidene-2-(2-methylprop-1-en-1-yl)-1-oxaspiro[4.5]decane)

3D MOL for NP0241112 ((2s,5r,7s,8s)-7-bromo-8-chloro-8-methyl-4-methylidene-2-(2-methylprop-1-en-1-yl)-1-oxaspiro[4.5]decane)

3D SDF for NP0241112 ((2s,5r,7s,8s)-7-bromo-8-chloro-8-methyl-4-methylidene-2-(2-methylprop-1-en-1-yl)-1-oxaspiro[4.5]decane)

3D-SDF for NP0241112 ((2s,5r,7s,8s)-7-bromo-8-chloro-8-methyl-4-methylidene-2-(2-methylprop-1-en-1-yl)-1-oxaspiro[4.5]decane)

PDB for NP0241112 ((2s,5r,7s,8s)-7-bromo-8-chloro-8-methyl-4-methylidene-2-(2-methylprop-1-en-1-yl)-1-oxaspiro[4.5]decane)

3D PDB for NP0241112 ((2s,5r,7s,8s)-7-bromo-8-chloro-8-methyl-4-methylidene-2-(2-methylprop-1-en-1-yl)-1-oxaspiro[4.5]decane)

SMILES for NP0241112 ((2s,5r,7s,8s)-7-bromo-8-chloro-8-methyl-4-methylidene-2-(2-methylprop-1-en-1-yl)-1-oxaspiro[4.5]decane)

INCHI for NP0241112 ((2s,5r,7s,8s)-7-bromo-8-chloro-8-methyl-4-methylidene-2-(2-methylprop-1-en-1-yl)-1-oxaspiro[4.5]decane)

Structure for NP0241112 ((2s,5r,7s,8s)-7-bromo-8-chloro-8-methyl-4-methylidene-2-(2-methylprop-1-en-1-yl)-1-oxaspiro[4.5]decane)

3D Structure for NP0241112 ((2s,5r,7s,8s)-7-bromo-8-chloro-8-methyl-4-methylidene-2-(2-methylprop-1-en-1-yl)-1-oxaspiro[4.5]decane)