NP-MRD: Showing NP-Card for Pentanedioic acid 2-(1-methylethylidene)-5-methyl ester (NP0004411)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-12-09 01:52:48 UTC

Updated at

2021-07-15 16:49:07 UTC

NP-MRD ID

NP0004411

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pentanedioic acid 2-(1-methylethylidene)-5-methyl ester

Provided By

NPAtlas

Description

Pentanedioic acid 2-(1-methylethylidene)-5-methyl ester is found in Acremonium sp. Pentanedioic acid 2-(1-methylethylidene)-5-methyl ester was first documented in 2002 (PMID: 12444684). Based on a literature review very few articles have been published on 5-methoxy-5-oxo-2-(propan-2-ylidene)pentanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118063D          

 27 26  0  0  0  0            999 V2000
    3.7334   -0.3905    0.9141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855    0.3383    0.5620 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1309    0.5054   -0.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7942   -0.0337   -1.6510 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    1.2737   -1.0235 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3382    0.5578   -1.2722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8816   -0.2772   -0.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2609   -1.5131    0.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7360   -2.2605    1.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8998   -2.0232   -0.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014    0.0752    0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6533    1.3425   -0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6386   -0.7057    1.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -1.1203    1.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5147    0.2393    1.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1465   -0.9784    0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1611    1.8127   -2.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7714    2.1214   -0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0690    1.3592   -1.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165   -0.0414   -2.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7728   -2.5685   -1.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0253    1.2768   -1.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5257    1.5621    0.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9347    2.1582    0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9735   -1.7016    1.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0212   -0.8214    2.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6015   -0.1870    1.7570 H   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
  3  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
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  2  3  0  0  0
 11 12  1  0  0  0  0
 11 13  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
  5 17  1  0  0  0  0
  5 18  1  0  0  0  0
  6 19  1  0  0  0  0
  6 20  1  0  0  0  0
 10 21  1  0  0  0  0
 12 22  1  0  0  0  0
 12 23  1  0  0  0  0
 12 24  1  0  0  0  0
 13 25  1  0  0  0  0
 13 26  1  0  0  0  0
 13 27  1  0  0  0  0
M  END


  Mrv1652306242118063D          

 27 26  0  0  0  0            999 V2000
    3.7334   -0.3905    0.9141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855    0.3383    0.5620 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1309    0.5054   -0.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7942   -0.0337   -1.6510 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    1.2737   -1.0235 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3382    0.5578   -1.2722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8816   -0.2772   -0.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2609   -1.5131    0.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7360   -2.2605    1.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8998   -2.0232   -0.3678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014    0.0752    0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6533    1.3425   -0.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6386   -0.7057    1.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -1.1203    1.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5147    0.2393    1.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1465   -0.9784    0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1611    1.8127   -2.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7714    2.1214   -0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0690    1.3592   -1.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165   -0.0414   -2.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7728   -2.5685   -1.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0253    1.2768   -1.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5257    1.5621    0.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9347    2.1582    0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9735   -1.7016    1.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0212   -0.8214    2.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6015   -0.1870    1.7570 H   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
  3  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
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  2  3  0  0  0
 11 12  1  0  0  0  0
 11 13  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
  5 17  1  0  0  0  0
  5 18  1  0  0  0  0
  6 19  1  0  0  0  0
  6 20  1  0  0  0  0
 10 21  1  0  0  0  0
 12 22  1  0  0  0  0
 12 23  1  0  0  0  0
 12 24  1  0  0  0  0
 13 25  1  0  0  0  0
 13 26  1  0  0  0  0
 13 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004411

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])C(=O)OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C9H14O4/c1-6(2)7(9(11)12)4-5-8(10)13-3/h4-5H2,1-3H3,(H,11,12)

> <INCHI_KEY>
OHTIESUYKHMKOD-UHFFFAOYSA-N

> <FORMULA>
C9H14O4

> <MOLECULAR_WEIGHT>
186.207

> <EXACT_MASS>
186.089208931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.02032467883983

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methoxy-5-oxo-2-(propan-2-ylidene)pentanoic acid

> <ALOGPS_LOGP>
1.14

> <JCHEM_LOGP>
1.273283669333333

> <ALOGPS_LOGS>
-1.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.535858734102081

> <JCHEM_PKA_STRONGEST_BASIC>
-7.027661324922287

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
47.2405

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methoxy-5-oxo-2-(propan-2-ylidene)pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.733  -0.391   0.914  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.586   0.338   0.562  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.131   0.505  -0.734  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.794  -0.034  -1.651  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.938   1.274  -1.024  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.338   0.558  -1.272  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.882  -0.277  -0.213  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.261  -1.513   0.192  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.736  -2.260   1.118  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.900  -2.023  -0.368  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.001   0.075   0.401  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.653   1.343  -0.045  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.639  -0.706   1.490  0.00  0.00           C+0
HETATM   14  H   UNK     0       3.429  -1.120   1.721  0.00  0.00           H+0
HETATM   15  H   UNK     0       4.515   0.239   1.381  0.00  0.00           H+0
HETATM   16  H   UNK     0       4.146  -0.978   0.063  0.00  0.00           H+0
HETATM   17  H   UNK     0       1.161   1.813  -2.003  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.771   2.121  -0.299  0.00  0.00           H+0
HETATM   19  H   UNK     0      -1.069   1.359  -1.611  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.217  -0.041  -2.237  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.773  -2.568  -1.229  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.025   1.277  -1.083  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.526   1.562   0.626  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.935   2.158   0.042  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.974  -1.702   1.118  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.021  -0.821   2.383  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.602  -0.187   1.757  0.00  0.00           H+0
CONECT    1    2   14   15   16                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   17   18                                             
CONECT    6    5    7   19   20                                             
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   21                                                       
CONECT   11    7   12   13                                                  
CONECT   12   11   22   23   24                                             
CONECT   13   11   25   26   27                                             
CONECT   14    1                                                            
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    5                                                            
CONECT   18    5                                                            
CONECT   19    6                                                            
CONECT   20    6                                                            
CONECT   21   10                                                            
CONECT   22   12                                                            
CONECT   23   12                                                            
CONECT   24   12                                                            
CONECT   25   13                                                            
CONECT   26   13                                                            
CONECT   27   13                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
5-Methoxy-5-oxo-2-(propan-2-ylidene)pentanoate	Generator

Chemical Formula

C₉H₁₄O₄

Average Mass

186.2070 Da

Monoisotopic Mass

186.08921 Da

IUPAC Name

5-methoxy-5-oxo-2-(propan-2-ylidene)pentanoic acid

Traditional Name

5-methoxy-5-oxo-2-(propan-2-ylidene)pentanoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)CCC(=C(C)C)C(O)=O

InChI Identifier

InChI=1S/C9H14O4/c1-6(2)7(9(11)12)4-5-8(10)13-3/h4-5H2,1-3H3,(H,11,12)

InChI Key

OHTIESUYKHMKOD-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Acremonium sp.	NPAtlas	12444684

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Fatty acid methyl ester
Fatty acid ester
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Methyl ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	1.14	ALOGPS
logP	1.27	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	4.54	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	47.24 m³·mol⁻¹	ChemAxon
Polarizability	19.02 Å³	ChemAxon
Number of Rings	0	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

NPAtlas ID

NPA009948

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9194757

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11019575

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abdel-Lateff A, Konig GM, Fisch KM, Holler U, Jones PG, Wright AD: New antioxidant hydroquinone derivatives from the algicolous marine fungus Acremonium sp. J Nat Prod. 2002 Nov;65(11):1605-11. doi: 10.1021/np020128p. [PubMed:12444684 ]

Showing NP-Card for Pentanedioic acid 2-(1-methylethylidene)-5-methyl ester (NP0004411)

MOL for NP0004411 (Pentanedioic acid 2-(1-methylethylidene)-5-methyl ester)

3D MOL for NP0004411 (Pentanedioic acid 2-(1-methylethylidene)-5-methyl ester)

3D SDF for NP0004411 (Pentanedioic acid 2-(1-methylethylidene)-5-methyl ester)

3D-SDF for NP0004411 (Pentanedioic acid 2-(1-methylethylidene)-5-methyl ester)

PDB for NP0004411 (Pentanedioic acid 2-(1-methylethylidene)-5-methyl ester)

3D PDB for NP0004411 (Pentanedioic acid 2-(1-methylethylidene)-5-methyl ester)

SMILES for NP0004411 (Pentanedioic acid 2-(1-methylethylidene)-5-methyl ester)

INCHI for NP0004411 (Pentanedioic acid 2-(1-methylethylidene)-5-methyl ester)

Structure for NP0004411 (Pentanedioic acid 2-(1-methylethylidene)-5-methyl ester)

3D Structure for NP0004411 (Pentanedioic acid 2-(1-methylethylidene)-5-methyl ester)