NP-MRD: Showing NP-Card for (1s,3s,5z,6r,7s,9s)-5-(1-bromopropylidene)-9-[(1s,2z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0³,⁷]nonane (NP0311931)

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Record Information

Version

2.0

Created at

2022-09-11 08:16:05 UTC

Updated at

2022-09-11 08:16:06 UTC

NP-MRD ID

NP0311931

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,5z,6r,7s,9s)-5-(1-bromopropylidene)-9-[(1s,2z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0³,⁷]nonane

Description

(1S,3S,5Z,6R,7S,9S)-5-(1-bromopropylidene)-9-[(1S,2Z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0³,⁷]Nonane belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. (1s,3s,5z,6r,7s,9s)-5-(1-bromopropylidene)-9-[(1s,2z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0³,⁷]nonane is found in Laurencia obtusa. Based on a literature review very few articles have been published on (1S,3S,5Z,6R,7S,9S)-5-(1-bromopropylidene)-9-[(1S,2Z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0³,⁷]Nonane.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    2.8103    1.7809   -3.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8913    1.0054   -2.9046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7958    0.0986   -2.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4984   -0.3176   -1.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.1593   -0.3407 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0583   -0.0858   -0.6370 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0145   -0.3090    1.0030 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2967   -1.7475    1.3344 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3036   -2.7427    0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9549   -2.3296    1.5745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8413   -1.5766    0.7902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4842   -0.2423    0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1009    0.6994    0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6378    0.2969   -0.9695 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6520    2.1086    0.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2948    2.6037   -1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3168   -0.0814    1.6199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4126   -1.3018    2.5372 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9134   -1.7054    2.7105 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6086    2.4614   -3.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277   -0.2338   -3.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3390   -0.9955   -1.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1928    1.2881   -0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358    0.2506    1.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3432   -2.0345    1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2289   -2.9463   -0.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6040   -3.7227    1.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4700   -3.1591    2.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4576    2.7874    0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7981    2.2545    0.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4596    1.7619   -1.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481    2.9224   -1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087    3.4008   -1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3646    0.7972    2.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9770   -1.1456    3.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 13  1  0
 13 14  1  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8 19  1  0
 19 18  1  0
 18 17  1  0
 17  7  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  3  0
 17 12  1  0
 18 10  1  0
  7  8  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 15 29  1  0
 15 30  1  0
 10 28  1  1
  9 26  1  0
  9 27  1  0
  8 25  1  1
 18 35  1  1
 17 34  1  1
  7 24  1  1
  5 23  1  1
  4 22  1  0
  3 21  1  0
  1 20  1  0
M  END


  Mrv1652309112210162D          

 19 21  0  0  1  0            999 V2000
    0.5435   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5366   -0.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5298   -1.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2408   -2.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9587   -1.8171    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6697   -2.2355    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9655   -0.9921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2894   -0.4343    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3035    0.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1808    0.8323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0598    0.8092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3351    0.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1178   -0.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7351    0.2992    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.2832   -1.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0658   -1.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6160   -0.4733    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0865    0.1021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0937    0.1255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 12  1  6  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
  8 19  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0311931

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C(Br)=C1\O[C@H]2C[C@@H]3O[C@H]2[C@H]1[C@@H]3[C@@H](Cl)\C=C/C#C

> <INCHI_IDENTIFIER>
InChI=1S/C15H16BrClO2/c1-3-5-6-9(17)12-10-7-11-15(18-10)13(12)14(19-11)8(16)4-2/h1,5-6,9-13,15H,4,7H2,2H3/b6-5-,14-8-/t9-,10-,11-,12+,13-,15+/m0/s1

> <INCHI_KEY>
AYFFHUILZXJDLN-IMGNLZAJSA-N

> <FORMULA>
C15H16BrClO2

> <MOLECULAR_WEIGHT>
343.65

> <EXACT_MASS>
342.00222

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.337533160409635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,5Z,6R,7S,9S)-5-(1-bromopropylidene)-9-[(1S,2Z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0^{3,7}]nonane

> <JCHEM_LOGP>
2.476017056

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.104999071968585

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
81.1911

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,5Z,6R,7S,9S)-5-(1-bromopropylidene)-9-[(1S,2Z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0^{3,7}]nonane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       1.014  -0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.002  -1.830   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.989  -3.370   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.316  -4.151   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.656  -3.392   0.000  0.00  0.00           C+0
HETATM    6 Cl   UNK     0       4.983  -4.173   0.000  0.00  0.00          Cl+0
HETATM    7  C   UNK     0       3.669  -1.852   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.407  -0.811   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.433   1.227   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.071   1.554   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.712   1.510   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.226   0.024   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.687  -0.463   0.000  0.00  0.00           C+0
HETATM   14 Br   UNK     0       8.839   0.559   0.000  0.00  0.00          Br+0
HETATM   15  C   UNK     0       7.995  -1.972   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.456  -2.459   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.883  -0.884   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.895   0.191   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.042   0.234   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   17                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   12    7   18                                                  
CONECT   18   17   10   19                                                  
CONECT   19   18    8                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆BrClO₂

Average Mass

343.6500 Da

Monoisotopic Mass

342.00222 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC\C(Br)=C1\O[C@H]2C[C@@H]3O[C@H]2[C@H]1[C@@H]3[C@@H](Cl)\C=C/C#C

InChI Identifier

InChI=1S/C15H16BrClO2/c1-3-5-6-9(17)12-10-7-11-15(18-10)13(12)14(19-11)8(16)4-2/h1,5-6,9-13,15H,4,7H2,2H3/b6-5-,14-8-/t9-,10-,11-,12+,13-,15+/m0/s1

InChI Key

AYFFHUILZXJDLN-IMGNLZAJSA-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 obtusa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furofurans

Sub Class

Not Available

Direct Parent

Furofurans

Alternative Parents

Substituents

Furofuran
Oxepane
Tetrahydrofuran
Acetylide
Dialkyl ether
Ether
Vinyl bromide
Vinyl halide
Haloalkene
Bromoalkene
Oxacycle
Organochloride
Organooxygen compound
Hydrocarbon derivative
Alkyl chloride
Alkyl halide
Organic oxygen compound
Organohalogen compound
Organobromide
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	2.48	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.19 m³·mol⁻¹	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

163188750

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,5z,6r,7s,9s)-5-(1-bromopropylidene)-9-[(1s,2z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0³,⁷]nonane (NP0311931)

MOL for NP0311931 ((1s,3s,5z,6r,7s,9s)-5-(1-bromopropylidene)-9-[(1s,2z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0³,⁷]nonane)

3D MOL for NP0311931 ((1s,3s,5z,6r,7s,9s)-5-(1-bromopropylidene)-9-[(1s,2z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0³,⁷]nonane)

3D SDF for NP0311931 ((1s,3s,5z,6r,7s,9s)-5-(1-bromopropylidene)-9-[(1s,2z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0³,⁷]nonane)

3D-SDF for NP0311931 ((1s,3s,5z,6r,7s,9s)-5-(1-bromopropylidene)-9-[(1s,2z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0³,⁷]nonane)

PDB for NP0311931 ((1s,3s,5z,6r,7s,9s)-5-(1-bromopropylidene)-9-[(1s,2z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0³,⁷]nonane)

3D PDB for NP0311931 ((1s,3s,5z,6r,7s,9s)-5-(1-bromopropylidene)-9-[(1s,2z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0³,⁷]nonane)

SMILES for NP0311931 ((1s,3s,5z,6r,7s,9s)-5-(1-bromopropylidene)-9-[(1s,2z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0³,⁷]nonane)

INCHI for NP0311931 ((1s,3s,5z,6r,7s,9s)-5-(1-bromopropylidene)-9-[(1s,2z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0³,⁷]nonane)

Structure for NP0311931 ((1s,3s,5z,6r,7s,9s)-5-(1-bromopropylidene)-9-[(1s,2z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0³,⁷]nonane)

3D Structure for NP0311931 ((1s,3s,5z,6r,7s,9s)-5-(1-bromopropylidene)-9-[(1s,2z)-1-chloropent-2-en-4-yn-1-yl]-4,8-dioxatricyclo[4.2.1.0³,⁷]nonane)