NP-MRD: Showing NP-Card for 5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde (NP0211917)

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Record Information

Version

2.0

Created at

2022-09-05 10:23:39 UTC

Updated at

2022-09-05 10:23:40 UTC

NP-MRD ID

NP0211917

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde

Description

5-(2-{4-Hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]Octane-2,2'-oxane]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. 5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde is found in Tricholoma pardinum. Based on a literature review very few articles have been published on 5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]Octane-2,2'-oxane]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052212232D          

 30 33  0  0  0  0            999 V2000
    8.1939    1.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3712    1.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0132    0.7206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4779    0.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1199   -0.7044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1905    0.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3940   -0.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4385    0.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7258    1.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9031    1.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5451    0.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7224    0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3644   -0.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -0.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770    0.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4350    1.0942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577    1.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7190   -0.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8963   -0.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5383   -1.1973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0111    0.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2498    0.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6123    1.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9703    1.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7896    0.9709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4316    0.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3237    0.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2658   -0.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0838    2.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9065    2.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
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  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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  9 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309052212232D          

 30 33  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0211917

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C=O)C(C)(C)C(CCC2CCC3(OC2)OC2(O)CCC3(C)OC2(C)C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O5/c1-17-7-9-19(21(2,3)20(17)15-26)10-8-18-11-12-25(28-16-18)23(6)13-14-24(27,30-25)22(4,5)29-23/h15,18-19,27H,7-14,16H2,1-6H3

> <INCHI_KEY>
YVVBWHWZYRDAJE-UHFFFAOYSA-N

> <FORMULA>
C25H40O5

> <MOLECULAR_WEIGHT>
420.59

> <EXACT_MASS>
420.287574388

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
48.75377305916196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxane]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde

> <JCHEM_LOGP>
4.726219101

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.931712416866372

> <JCHEM_PKA_STRONGEST_BASIC>
-3.770615784698179

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
116.70250000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxane]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      15.295   2.848   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.760   2.733   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.091   1.345   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.959   0.073   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      13.291  -1.315   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      11.556   1.230   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.936  -0.262   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.152   0.597   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.688   2.503   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.152   2.387   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.484   1.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.948   0.885   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.280  -0.502   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.745  -0.617   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.877   0.655   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.545   2.042   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.081   2.157   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.209  -0.732   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.673  -0.847   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.005  -2.235   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.887   0.189   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.333   1.114   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.010   1.927   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.678   3.315   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.474   1.812   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.806   0.425   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.604   1.044   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.496  -0.398   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.356   3.890   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.892   4.005   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   29                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18   23                                             
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15   19                                                       
CONECT   19   18   20   21   26                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   15   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   19   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    9   30                                                       
CONECT   30   29    2                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₄₀O₅

Average Mass

420.5900 Da

Monoisotopic Mass

420.28757 Da

IUPAC Name

5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxane]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde

Traditional Name

5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxane]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC1=C(C=O)C(C)(C)C(CCC2CCC3(OC2)OC2(O)CCC3(C)OC2(C)C)CC1

InChI Identifier

InChI=1S/C25H40O5/c1-17-7-9-19(21(2,3)20(17)15-26)10-8-18-11-12-25(28-16-18)23(6)13-14-24(27,30-25)22(4,5)29-23/h15,18-19,27H,7-14,16H2,1-6H3

InChI Key

YVVBWHWZYRDAJE-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

Species Name	Source	Reference
Tricholoma pardinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Oxane
Para-dioxane
Hemiacetal
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aldehyde
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	4.73	ChemAxon
pKa (Strongest Acidic)	10.93	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.7 m³·mol⁻¹	ChemAxon
Polarizability	48.75 Å³	ChemAxon
Number of Rings	4	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

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

162814386

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde (NP0211917)

MOL for NP0211917 (5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde)

3D MOL for NP0211917 (5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde)

3D SDF for NP0211917 (5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde)

3D-SDF for NP0211917 (5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde)

PDB for NP0211917 (5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde)

3D PDB for NP0211917 (5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde)

SMILES for NP0211917 (5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde)

INCHI for NP0211917 (5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde)

Structure for NP0211917 (5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde)

3D Structure for NP0211917 (5-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde)