NP-MRD: Showing NP-Card for 4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene (NP0214885)

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Record Information

Version

2.0

Created at

2022-09-05 14:18:34 UTC

Updated at

2022-09-05 14:18:34 UTC

NP-MRD ID

NP0214885

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene

Description

4-(3-Bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]Dodeca-1(12),8,10-triene belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. 4-(3-Bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]Dodeca-1(12),8,10-triene is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -2.4332    2.2122    0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8662    1.1253   -0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4802   -0.2193    0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4494   -1.0346    0.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2084   -2.3070    1.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9206   -2.7913    0.9095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9169   -1.9913    0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1943   -0.7165   -0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0504   -0.1274   -0.6030 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6830    0.6878    0.3321 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048    0.7375   -0.1067 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8420    1.3791    0.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1174    1.4883    0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3912    1.4054    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2839   -0.1583    0.7452 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.3248   -0.7589   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0108   -1.2932   -0.7220 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4346   -2.2323    0.1516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4260    1.8509    1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4734    2.6881    0.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1887    3.0231    0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9696    1.1675   -0.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4944    1.3542   -1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4888   -0.6834    0.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0041   -2.9356    1.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7376   -3.7927    1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0390    0.3333   -1.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0494    1.2248   -1.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6081    1.7734    1.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7240    2.2606   -0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1632   -0.9160   -0.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5084   -1.0986    0.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0948   -1.6549   -1.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 11 12  1  0
 12 13  2  0
 13 14  2  0
 14 15  1  0
  8  3  1  0
 17  9  1  0
 18  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  9 27  1  6
 11 28  1  6
 16 31  1  0
 16 32  1  0
 17 33  1  6
 12 29  1  0
 14 30  1  0
M  END


  Mrv1533004201505052D          

 18 20  0  0  0  0            999 V2000
    0.6293   -1.7686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1933   -1.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539   -0.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505   -0.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890    0.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750    1.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785    1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9554    1.4863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6131    0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4379    0.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774    0.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005   -0.2892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427    0.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    0.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4568   -0.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0807    0.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7045    0.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5489    1.8020    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  2  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
  7 14  2  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0214885

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=CC=CC2=C1C1OC(CC1O2)C=C=CBr

> <INCHI_IDENTIFIER>
InChI=1S/C15H15BrO2/c1-2-10-5-3-7-12-14(10)15-13(18-12)9-11(17-15)6-4-8-16/h3,5-8,11,13,15H,2,9H2,1H3

> <INCHI_KEY>
SKPPEIDJGJGRGK-UHFFFAOYSA-N

> <FORMULA>
C15H15BrO2

> <MOLECULAR_WEIGHT>
307.187

> <EXACT_MASS>
306.025543

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.76228441170146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene

> <ALOGPS_LOGP>
4.10

> <JCHEM_LOGP>
3.9956297

> <ALOGPS_LOGS>
-3.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.160349266997345

> <JCHEM_POLAR_SURFACE_AREA>
18.46

> <JCHEM_REFRACTIVITY>
74.73250000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       1.175  -3.301   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.228  -2.177   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.781  -0.704   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.281  -0.354   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.166   1.120   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.887   2.244   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.387   1.894   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.650   2.774   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.878   1.845   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.417   1.814   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.864   0.341   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.601  -0.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.373   0.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.833   0.420   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.319  -0.164   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.484   0.844   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.648   1.851   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0      10.358   3.364   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12    9   14                                                  
CONECT   14   13    3    7                                                  
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₅BrO₂

Average Mass

307.1870 Da

Monoisotopic Mass

306.02554 Da

IUPAC Name

4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene

Traditional Name

4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene

CAS Registry Number

Not Available

SMILES

CCC1=CC=CC2=C1C1OC(CC1O2)C=C=CBr

InChI Identifier

InChI=1S/C15H15BrO2/c1-2-10-5-3-7-12-14(10)15-13(18-12)9-11(17-15)6-4-8-16/h3,5-8,11,13,15H,2,9H2,1H3

InChI Key

SKPPEIDJGJGRGK-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Coumarans

Sub Class

Not Available

Direct Parent

Coumarans

Alternative Parents

Substituents

Coumaran
Alkyl aryl ether
Benzenoid
Oxolane
Oxacycle
Vinyl halide
Vinyl bromide
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organobromide
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.1	ALOGPS
logP	4	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	-4.2	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	2	ChemAxon
Refractivity	74.73 m³·mol⁻¹	ChemAxon
Polarizability	28.76 Å³	ChemAxon
Number of Rings	3	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

23424610

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene (NP0214885)

MOL for NP0214885 (4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene)

3D MOL for NP0214885 (4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene)

3D SDF for NP0214885 (4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene)

3D-SDF for NP0214885 (4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene)

PDB for NP0214885 (4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene)

3D PDB for NP0214885 (4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene)

SMILES for NP0214885 (4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene)

INCHI for NP0214885 (4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene)

Structure for NP0214885 (4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene)

3D Structure for NP0214885 (4-(3-bromopropa-1,2-dien-1-yl)-12-ethyl-3,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(8),9,11-triene)