NP-MRD: Showing NP-Card for 6-ethyl-7,9-dimethyl-4,8-dioxospiro[4.5]dec-6-ene-1-carboxylic acid (NP0187366)

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Record Information

Version

2.0

Created at

2022-09-04 03:30:58 UTC

Updated at

2022-09-04 03:30:58 UTC

NP-MRD ID

NP0187366

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-ethyl-7,9-dimethyl-4,8-dioxospiro[4.5]dec-6-ene-1-carboxylic acid

Description

Spirodionic acid, also known as spirodionate, belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. Based on a literature review very few articles have been published on Spirodionic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.1231   -3.0218   -1.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1102   -2.2341    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5005   -0.8252    0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6701   -0.4977    0.6745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4712   -1.5364    1.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1533    0.8674    0.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0133    1.2840    1.4584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6478    1.8042   -0.3684 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1920    3.1052    0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5112    1.3042   -1.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3130    0.1889   -0.5456 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0338   -0.4226   -1.7246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4944   -0.6628   -2.7710 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4569   -0.6406   -1.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6740    0.4850   -0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3684    0.8350    0.2856 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3558    0.5437    1.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5041   -0.1984    2.2262 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3299    1.1193    2.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2993   -4.1162   -0.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9309   -2.6989   -1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8339   -3.0629   -1.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7427   -2.7829    0.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9238   -2.3579    0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7099   -2.3892    0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4711   -1.1215    1.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0109   -1.9020    2.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4947    2.1613   -1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0564    3.7815    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7164    2.7936    1.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4278    3.5610   -0.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9153    0.9157   -2.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1817    2.1219   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5706   -1.6310   -0.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0498   -0.4820   -2.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3839    0.2409    0.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0071    1.3577   -0.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2730    1.9722    0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4141    2.1413    2.4496 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 16  1  0
 16 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  2  0
 16 17  1  0
 17 19  1  0
 17 18  2  0
 11  3  1  1
 12 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  5 25  1  0
  5 26  1  0
  5 27  1  0
  8 28  1  6
  9 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 16 38  1  1
 15 36  1  0
 15 37  1  0
 14 34  1  0
 14 35  1  0
 19 39  1  0
M  END


  Mrv1652309042205312D          

 19 20  0  0  0  0            999 V2000
    1.9759    2.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4649    1.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7704    1.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5868    1.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0978    1.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8923    0.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7087    0.1752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3813   -0.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868   -1.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5649   -0.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2594    0.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8943   -0.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2782   -0.9389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0779   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0616    0.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6687    1.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7873    1.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1396    2.4344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4218    2.4508    0.0000 O   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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0187366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=C(C)C(=O)C(C)CC11C(CCC1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-4-10-9(3)13(17)8(2)7-15(10)11(14(18)19)5-6-12(15)16/h8,11H,4-7H2,1-3H3,(H,18,19)

> <INCHI_KEY>
LFDLVXYMKUPPOT-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.321

> <EXACT_MASS>
264.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.658184392625465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-ethyl-7,9-dimethyl-4,8-dioxospiro[4.5]dec-6-ene-1-carboxylic acid

> <JCHEM_LOGP>
2.6804232543333337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.07084410404278

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.411087594989531

> <JCHEM_PKA_STRONGEST_BASIC>
-5.388880749293695

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
70.5119

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-ethyl-7,9-dimethyl-4,8-dioxospiro[4.5]dec-6-ene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       3.688   4.840   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.735   3.631   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.305   2.201   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.829   1.979   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.783   3.188   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.399   0.549   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.923   0.327   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.445  -0.661   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.015  -2.091   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.921  -0.439   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.351   0.991   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.669  -0.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.386  -1.753   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.145  -0.168   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.115   1.350   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.248   2.066   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.470   3.590   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.261   4.544   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.654   4.575   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    3   12   16                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
Spirodionate	Generator

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3210 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC1=C(C)C(=O)C(C)CC11C(CCC1=O)C(O)=O

InChI Identifier

InChI=1S/C15H20O4/c1-4-10-9(3)13(17)8(2)7-15(10)11(14(18)19)5-6-12(15)16/h8,11H,4-7H2,1-3H3,(H,18,19)

InChI Key

LFDLVXYMKUPPOT-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 iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

11-noriridane monoterpenoid
Cyclohexenone
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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

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

28284455

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60208865

PDB ID

Not Available

ChEBI ID

182910

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-ethyl-7,9-dimethyl-4,8-dioxospiro[4.5]dec-6-ene-1-carboxylic acid (NP0187366)

MOL for NP0187366 (6-ethyl-7,9-dimethyl-4,8-dioxospiro[4.5]dec-6-ene-1-carboxylic acid)

3D MOL for NP0187366 (6-ethyl-7,9-dimethyl-4,8-dioxospiro[4.5]dec-6-ene-1-carboxylic acid)

3D SDF for NP0187366 (6-ethyl-7,9-dimethyl-4,8-dioxospiro[4.5]dec-6-ene-1-carboxylic acid)

3D-SDF for NP0187366 (6-ethyl-7,9-dimethyl-4,8-dioxospiro[4.5]dec-6-ene-1-carboxylic acid)

PDB for NP0187366 (6-ethyl-7,9-dimethyl-4,8-dioxospiro[4.5]dec-6-ene-1-carboxylic acid)

3D PDB for NP0187366 (6-ethyl-7,9-dimethyl-4,8-dioxospiro[4.5]dec-6-ene-1-carboxylic acid)

SMILES for NP0187366 (6-ethyl-7,9-dimethyl-4,8-dioxospiro[4.5]dec-6-ene-1-carboxylic acid)

INCHI for NP0187366 (6-ethyl-7,9-dimethyl-4,8-dioxospiro[4.5]dec-6-ene-1-carboxylic acid)

Structure for NP0187366 (6-ethyl-7,9-dimethyl-4,8-dioxospiro[4.5]dec-6-ene-1-carboxylic acid)

3D Structure for NP0187366 (6-ethyl-7,9-dimethyl-4,8-dioxospiro[4.5]dec-6-ene-1-carboxylic acid)