NP-MRD: Showing NP-Card for Bombardolize A (E-isomer) (NP0025771)

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Record Information

Version

2.0

Created at

2021-06-19 17:48:19 UTC

Updated at

2021-06-29 23:50:55 UTC

NP-MRD ID

NP0025771

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bombardolize A (E-isomer)

Provided By

JEOL Database JEOL Logo

Description

(5E)-3-[(1E)-3-hydroxyprop-1-en-1-yl]-5-propylidene-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. Bombardolize A (E-isomer) is found in Bombardioidea anartia. Bombardolize A (E-isomer) was first documented in 2001 (Hein, S. M., et al.). Based on a literature review very few articles have been published on (5E)-3-[(1E)-3-hydroxyprop-1-en-1-yl]-5-propylidene-2,5-dihydrofuran-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119483D          

 25 25  0  0  0  0            999 V2000
    3.5737    1.5337   -1.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2632    1.0704   -1.8792 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3441   -0.3634   -2.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6558   -1.4014   -1.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7013   -1.4183   -0.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2449   -2.6561   -0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6869   -3.1876    0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6130   -2.4747    1.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5645   -3.0581    2.0013 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4251   -2.3246    3.2065 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9826   -3.4738   -1.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8572   -4.6811   -1.7340 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8264   -2.6844   -2.3331 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8168    0.9503   -0.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4036    1.4351   -1.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5027    2.5865   -0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0366    1.6890   -2.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4514    1.2351   -1.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0391   -0.5624   -3.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4072   -0.5592   -0.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6119   -4.2618    0.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7121   -1.4047    0.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3595   -4.1140    2.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5927   -2.9540    1.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0176   -2.7391    3.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  4 13  1  0  0  0  0
  7  8  2  0  0  0  0
 13 11  1  0  0  0  0
  4  3  2  0  0  0  0
 11  6  1  0  0  0  0
  3  2  1  0  0  0  0
  6  5  2  0  0  0  0
  2  1  1  0  0  0  0
  5  4  1  0  0  0  0
  8  9  1  0  0  0  0
 11 12  2  0  0  0  0
  9 10  1  0  0  0  0
  5 20  1  0  0  0  0
  7 21  1  0  0  0  0
  8 22  1  0  0  0  0
  3 19  1  0  0  0  0
  2 17  1  0  0  0  0
  2 18  1  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  9 23  1  0  0  0  0
  9 24  1  0  0  0  0
 10 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025771

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C(\[H])=C(/[H])C1=C([H])\C(\OC1=O)=C(\[H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O3/c1-2-4-9-7-8(5-3-6-11)10(12)13-9/h3-5,7,11H,2,6H2,1H3/b5-3+,9-4+

> <INCHI_KEY>
YGPGUEZTBZXORL-BMVOEDMYSA-N

> <FORMULA>
C10H12O3

> <MOLECULAR_WEIGHT>
180.203

> <EXACT_MASS>
180.078644246

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.573151943834333

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E)-3-[(1E)-3-hydroxyprop-1-en-1-yl]-5-propylidene-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
1.2300200763333333

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.185409581256675

> <JCHEM_PKA_STRONGEST_BASIC>
-2.28030184915833

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
52.735000000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5E)-3-[(1E)-3-hydroxyprop-1-en-1-yl]-5-propylidenefuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       3.574   1.534  -1.262  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.263   1.070  -1.879  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.344  -0.363  -2.317  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.656  -1.401  -1.827  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.701  -1.418  -0.774  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.245  -2.656  -0.608  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.687  -3.188   0.351  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.613  -2.475   1.012  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.564  -3.058   2.001  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.425  -2.325   3.207  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.983  -3.474  -1.595  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.857  -4.681  -1.734  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.826  -2.684  -2.333  0.00  0.00           O+0
HETATM   14  H   UNK     0       3.817   0.950  -0.367  0.00  0.00           H+0
HETATM   15  H   UNK     0       4.404   1.435  -1.970  0.00  0.00           H+0
HETATM   16  H   UNK     0       3.503   2.587  -0.970  0.00  0.00           H+0
HETATM   17  H   UNK     0       2.037   1.689  -2.755  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.451   1.235  -1.164  0.00  0.00           H+0
HETATM   19  H   UNK     0       3.039  -0.562  -3.132  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.407  -0.559  -0.192  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.612  -4.262   0.520  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.712  -1.405   0.849  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.360  -4.114   2.203  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.593  -2.954   1.642  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.018  -2.739   3.856  0.00  0.00           H+0
CONECT    1    2   14   15   16                                             
CONECT    2    3    1   17   18                                             
CONECT    3    4    2   19                                                  
CONECT    4   13    3    5                                                  
CONECT    5    6    4   20                                                  
CONECT    6    7   11    5                                                  
CONECT    7    6    8   21                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10   23   24                                             
CONECT   10    9   25                                                       
CONECT   11   13    6   12                                                  
CONECT   12   11                                                            
CONECT   13    4   11                                                       
CONECT   14    1                                                            
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    2                                                            
CONECT   18    2                                                            
CONECT   19    3                                                            
CONECT   20    5                                                            
CONECT   21    7                                                            
CONECT   22    8                                                            
CONECT   23    9                                                            
CONECT   24    9                                                            
CONECT   25   10                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₂O₃

Average Mass

180.2030 Da

Monoisotopic Mass

180.07864 Da

IUPAC Name

(5E)-3-[(1E)-3-hydroxyprop-1-en-1-yl]-5-propylidene-2,5-dihydrofuran-2-one

Traditional Name

(5E)-3-[(1E)-3-hydroxyprop-1-en-1-yl]-5-propylidenefuran-2-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C(\[H])=C(/[H])C1=C([H])\C(\OC1=O)=C(\[H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C10H12O3/c1-2-4-9-7-8(5-3-6-11)10(12)13-9/h3-5,7,11H,2,6H2,1H3/b5-3+,9-4+

InChI Key

YGPGUEZTBZXORL-BMVOEDMYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bombardioidea anartia	JEOL database	Hein, S. M., et al, J. Nat. Prod. 64, 809 (2001)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Enol ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	1.82	ALOGPS
logP	1.23	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	16.19	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	52.74 m³·mol⁻¹	ChemAxon
Polarizability	19.57 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

C00045690

Chemspider ID

9063781

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10888517

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hein, S. M., et al. (2001). Hein, S. M., et al, J. Nat. Prod. 64, 809 (2001). J. Nat. Prod..

Showing NP-Card for Bombardolize A (E-isomer) (NP0025771)

MOL for NP0025771 (Bombardolize A (E-isomer))

3D MOL for NP0025771 (Bombardolize A (E-isomer))

3D SDF for NP0025771 (Bombardolize A (E-isomer))

3D-SDF for NP0025771 (Bombardolize A (E-isomer))

PDB for NP0025771 (Bombardolize A (E-isomer))

3D PDB for NP0025771 (Bombardolize A (E-isomer))

SMILES for NP0025771 (Bombardolize A (E-isomer))

INCHI for NP0025771 (Bombardolize A (E-isomer))

Structure for NP0025771 (Bombardolize A (E-isomer))

3D Structure for NP0025771 (Bombardolize A (E-isomer))