NP-MRD: Showing NP-Card for 3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane (NP0298917)

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Record Information

Version

2.0

Created at

2022-09-10 10:27:32 UTC

Updated at

2022-09-10 10:27:32 UTC

NP-MRD ID

NP0298917

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane

Description

3-(1-Bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]Nonane belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms). 3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane is found in Laurencia venusta. 3-(1-Bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]Nonane is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    4.6666    2.1544    3.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9377    1.2864    2.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0625    0.2517    2.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1660   -0.2054    1.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502   -1.2790    0.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225   -0.8184   -0.6416 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5782    0.2930   -0.1825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7794    0.5558   -0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0663    1.7695   -0.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3771    2.7472    0.8188 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3688    2.4558   -0.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7830    2.7340    1.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9707   -0.0763   -1.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1104   -1.3952   -1.5636 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5972   -1.6356   -2.9545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5234   -2.5839   -1.7756 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0079   -2.8830   -1.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5278   -1.7654   -1.1557 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3927   -1.9568    0.4299 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3035    2.9107    3.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142   -0.1528    2.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9185    0.2088    0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6117   -1.6139    1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8723   -2.1240    0.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1409   -0.4004   -1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1296    3.4729   -0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1354    1.9648   -0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2629    3.6475    1.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8792    2.8057    1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4086    1.9101    2.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2801    0.6541   -1.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7402    0.0881   -0.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559   -1.4913   -1.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0343   -3.5290   -1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3702   -3.1390   -2.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1549   -3.8512   -1.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0355   -1.0097   -1.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11  9  1  0
  9 10  1  0
  9  8  2  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  3  0
  6  7  1  0
  7  8  1  0
 16 14  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 11 26  1  0
 11 27  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  6
 16 34  1  6
 17 35  1  0
 17 36  1  0
 18 37  1  6
  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


  Mrv1533004241500412D          

 19 20  0  0  0  0            999 V2000
    3.2192   -1.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -0.5807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0855   -0.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7698    0.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9448    0.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3614    0.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3530    1.2851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3614    1.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9448    2.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7698    2.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0855    3.0431    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3532    1.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1154    2.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230    2.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9852    3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0929    3.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2006    4.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3532    0.8726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5833   -1.1275    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  2  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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  4  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  3  0  0  0  0
 12 18  1  0  0  0  0
  4 18  1  0  0  0  0
  3 19  1  4  0  0  0
M  END
> <DATABASE_ID>
NP0298917

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(Br)=C1CC2OC2CC(Cl)C(CC=CC#C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H18BrClO2/c1-3-5-6-7-12-11(17)8-14-15(19-14)9-13(18-12)10(16)4-2/h1,5-6,11-12,14-15H,4,7-9H2,2H3

> <INCHI_KEY>
IPGHQCSIHTZTOJ-UHFFFAOYSA-N

> <FORMULA>
C15H18BrClO2

> <MOLECULAR_WEIGHT>
345.66

> <EXACT_MASS>
344.017871

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
31.625137548637813

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane

> <ALOGPS_LOGP>
4.29

> <JCHEM_LOGP>
3.0989346360000005

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.11358663453416

> <JCHEM_POLAR_SURFACE_AREA>
21.759999999999998

> <JCHEM_REFRACTIVITY>
83.25210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       6.009  -2.507   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.420  -1.084   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.893  -0.883   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.304   0.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.764   0.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.675   1.629   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.659   2.399   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.675   3.169   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.764   4.258   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.304   4.258   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0       3.893   5.681   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       4.393   3.169   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.815   3.758   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.016   5.285   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.439   5.874   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.640   7.401   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.841   8.928   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.393   1.629   0.000  0.00  0.00           O+0
HETATM   19 Br   UNK     0       2.955  -2.105   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    8                                                       
CONECT    8    7    6    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   12    4                                                       
CONECT   19    3                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈BrClO₂

Average Mass

345.6600 Da

Monoisotopic Mass

344.01787 Da

IUPAC Name

3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane

Traditional Name

3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane

CAS Registry Number

Not Available

SMILES

CCC(Br)=C1CC2OC2CC(Cl)C(CC=CC#C)O1

InChI Identifier

InChI=1S/C15H18BrClO2/c1-3-5-6-7-12-11(17)8-14-15(19-14)9-13(18-12)10(16)4-2/h1,5-6,11-12,14-15H,4,7-9H2,2H3

InChI Key

IPGHQCSIHTZTOJ-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 venusta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Epoxides

Sub Class

Not Available

Direct Parent

Epoxides

Alternative Parents

Substituents

Dialkyl ether
Oxirane
Ether
Vinyl bromide
Vinyl halide
Haloalkene
Bromoalkene
Oxacycle
Acetylide
Organooxygen compound
Alkyl chloride
Alkyl halide
Organohalogen compound
Organobromide
Hydrocarbon derivative
Organochloride
Organic oxygen compound
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	4.29	ALOGPS
logP	3.1	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-4.1	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	3	ChemAxon
Refractivity	83.25 m³·mol⁻¹	ChemAxon
Polarizability	31.63 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

73818195

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane (NP0298917)

MOL for NP0298917 (3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane)

3D MOL for NP0298917 (3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane)

3D SDF for NP0298917 (3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane)

3D-SDF for NP0298917 (3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane)

PDB for NP0298917 (3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane)

3D PDB for NP0298917 (3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane)

SMILES for NP0298917 (3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane)

INCHI for NP0298917 (3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane)

Structure for NP0298917 (3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane)

3D Structure for NP0298917 (3-(1-bromopropylidene)-6-chloro-5-(pent-2-en-4-yn-1-yl)-4,9-dioxabicyclo[6.1.0]nonane)