NP-MRD: Showing NP-Card for 6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione (NP0227824)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 07:17:05 UTC

Updated at

2022-09-06 07:17:05 UTC

NP-MRD ID

NP0227824

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione

Description

Umbellifolide belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Umbellifolide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Umbellifolide has been detected, but not quantified in, herbs and spices and tea. This could make umbellifolide a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -4.0308    1.9705   -1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7087    0.9901   -0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296    0.9539    1.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2873    1.9054    1.9380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6833   -0.3271    1.5796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8066   -0.9804    0.6388 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4515   -1.0608    1.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3289   -0.7021    0.2520 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0250   -1.9816   -0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9184   -0.3018    0.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0827   -0.0479    0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3290    0.3445    0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4617    0.5873   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8163    0.9879    0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2603    0.4508   -1.2359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7324    0.3206   -0.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566    1.4133   -0.8910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9067   -0.0784   -1.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0522   -0.2915   -0.6274 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8157    1.8816   -2.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5123    2.8857   -0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2293   -2.0228    0.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3643   -0.3409    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2333   -2.0563    1.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3410   -1.7424   -1.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958   -2.5188   -0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6535   -2.5916    0.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1263   -1.0894    1.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6442    0.6169    1.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2962   -0.9610   -0.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850    0.8321   -0.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5531   -0.4346    1.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1383    1.2812    1.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3584    1.4394   -0.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3931    0.0655    0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7756    1.7292    1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1500    0.7187   -2.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6972   -1.0139   -2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8357   -0.8314   -1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  2  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
  8 10  1  1
  8  9  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  2  0
 16  8  1  0
 19  6  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 12 32  1  0
 12 33  1  0
 11 30  1  0
 11 31  1  0
 10 28  1  0
 10 29  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
  7 23  1  0
  7 24  1  0
  6 22  1  6
  1 20  1  0
  1 21  1  0
 19 39  1  6
 18 37  1  0
 18 38  1  0
M  END


  Mrv0541 05061310162D          

 19 20  0  0  0  0            999 V2000
   -1.4929    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0368    2.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    4.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6505    3.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3650    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1741    2.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6098    4.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784    3.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5289    3.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7044    3.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4222    4.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3616    2.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7563    4.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0795    3.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784    4.5142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8313    2.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315    4.5067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0723    4.6859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  2  2  0  0  0  0
 11  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 15  3  1  0  0  0  0
 15  6  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16  9  2  0  0  0  0
 17 13  2  0  0  0  0
 18 14  2  0  0  0  0
 19 12  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0227824

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)CCCC1(C)CC2OC(=O)C(=C)C2CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-9(16)5-4-6-15(3)8-12-11(7-13(15)17)10(2)14(18)19-12/h11-12H,2,4-8H2,1,3H3

> <INCHI_KEY>
MIRSLSRVCIOISZ-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.089192224975612

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-methyl-3-methylidene-6-(4-oxopentyl)-octahydro-1-benzofuran-2,5-dione

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
2.381977904333333

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.645149613474977

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.324156149594263

> <JCHEM_PKA_STRONGEST_BASIC>
-6.652524174820898

> <JCHEM_POLAR_SURFACE_AREA>
60.44

> <JCHEM_REFRACTIVITY>
69.6356

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.787   6.117   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.402   5.192   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.892   8.066   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.214   6.887   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.119   6.117   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.548   6.117   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.925   5.172   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.872   8.066   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.453   6.887   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.454   6.405   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.915   6.352   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.388   7.799   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.408   5.439   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.878   7.886   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.882   6.887   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.453   8.427   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.418   4.260   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.325   8.413   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.602   8.747   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   15                                                            
CONECT    4    5    6                                                       
CONECT    5    4    9                                                       
CONECT    6    4   15                                                       
CONECT    7   11   13                                                       
CONECT    8   12   15                                                       
CONECT    9    1    5   16                                                  
CONECT   10    2   11   14                                                  
CONECT   11    7   10   12                                                  
CONECT   12    8   11   19                                                  
CONECT   13    7   15   17                                                  
CONECT   14   10   18   19                                                  
CONECT   15    3    6    8   13                                             
CONECT   16    9                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
(+)-Umbellifolide	HMDB
4,5-Dioxo-4,5-seco-11(13)-eudesmen-12,8b-olide	HMDB
Tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-2,5-(3H,4H)-benzofurandione, 9ci	HMDB
[3AR-(3aalpha,6alpha,7aalpha)]-tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-2,5(3H,4H)-benzofurandione	HMDB

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3169 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

6-methyl-3-methylidene-6-(4-oxopentyl)-octahydro-1-benzofuran-2,5-dione

Traditional Name

6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione

CAS Registry Number

Not Available

SMILES

CC(=O)CCCC1(C)CC2OC(=O)C(=C)C2CC1=O

InChI Identifier

InChI=1S/C15H20O4/c1-9(16)5-4-6-15(3)8-12-11(7-13(15)17)10(2)14(18)19-12/h11-12H,2,4-8H2,1,3H3

InChI Key

MIRSLSRVCIOISZ-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 benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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	1.38	ALOGPS
logP	2.38	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	17.32	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.64 m³·mol⁻¹	ChemAxon
Polarizability	28.09 Å³	ChemAxon
Number of Rings	2	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

HMDB0038156

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017385

KNApSAcK ID

C00013211

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

13889981

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione (NP0227824)

MOL for NP0227824 (6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione)

3D MOL for NP0227824 (6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione)

3D SDF for NP0227824 (6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione)

3D-SDF for NP0227824 (6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione)

PDB for NP0227824 (6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione)

3D PDB for NP0227824 (6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione)

SMILES for NP0227824 (6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione)

INCHI for NP0227824 (6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione)

Structure for NP0227824 (6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione)

3D Structure for NP0227824 (6-methyl-3-methylidene-6-(4-oxopentyl)-tetrahydro-1-benzofuran-2,5-dione)