NP-MRD: Showing NP-Card for 2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6,8(12),13-trien-11-one (NP0308049)

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Record Information

Version

2.0

Created at

2022-09-11 01:35:03 UTC

Updated at

2022-09-11 01:35:04 UTC

NP-MRD ID

NP0308049

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6,8(12),13-trien-11-one

Description

2,2,7,7-Tetramethyl-1,6-dioxaspiro[4.4]Non-3-ene 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. 2,2,7,7-Tetramethyl-1,6-dioxaspiro[4.4]Non-3-ene is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2,2,7,7-Tetramethyl-1,6-dioxaspiro[4.4]Non-3-ene has been detected, but not quantified in, alcoholic beverages. 2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6,8(12),13-trien-11-one is found in Aspergillus ustus. This could make 2,2,7,7-tetramethyl-1,6-dioxaspiro[4.4]Non-3-ene a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061304582D          

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M  END

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  Mrv0541 05061304582D          

 34 39  0  0  0  0            999 V2000
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 31 21  1  0  0  0  0
 32 19  1  0  0  0  0
 32 24  1  0  0  0  0
 33 22  1  0  0  0  0
 33 25  1  0  0  0  0
 34 25  1  0  0  0  0
 34 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0308049

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(=O)OCC2=C(C)C2=C1CC1C(C)(CC(O)C34OC(CCC13C)(OC)OC4(C)C)O2

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O8/c1-13-15-12-31-21(28)18(15)20(29-6)14-10-16-23(4)8-9-25(30-7)33-22(2,3)26(23,34-25)17(27)11-24(16,5)32-19(13)14/h16-17,27H,8-12H2,1-7H3

> <INCHI_KEY>
ZVFMDVFPBVFGPG-UHFFFAOYSA-N

> <FORMULA>
C26H34O8

> <MOLECULAR_WEIGHT>
474.5434

> <EXACT_MASS>
474.225368064

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
50.1667537636292

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6(14),7,12-trien-11-one

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
3.5700055900000005

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.20598961075536

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.766197386117426

> <JCHEM_PKA_STRONGEST_BASIC>
-3.331152588815547

> <JCHEM_POLAR_SURFACE_AREA>
92.68000000000002

> <JCHEM_REFRACTIVITY>
122.40169999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6(14),7,12-trien-11-one

> <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      11.471  -1.596   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.820  -0.774   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.085  -0.029   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.639   2.965   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.407  -1.522   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.595   5.460   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.866   5.879   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.304   3.663   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.828   4.271   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.050   2.498   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.956  -1.017   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.913   0.691   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.206  -0.079   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.496   1.968   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.388   0.909   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.868   1.510   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.490  -0.490   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.124   2.426   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.760   0.451   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.678   2.956   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.485   3.146   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.456   0.672   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.405   2.043   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.133  -0.007   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.535   3.297   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.091   1.052   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.738  -1.802   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      13.702   4.671   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      10.413   4.473   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.455   4.395   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      14.591   2.074   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.579  -0.536   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.541   2.023   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       3.382   2.203   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   22                                                            
CONECT    3   22                                                            
CONECT    4   23                                                            
CONECT    5   24                                                            
CONECT    6   29                                                            
CONECT    7   30                                                            
CONECT    8    9   23                                                       
CONECT    9    8   25                                                       
CONECT   10   14   16                                                       
CONECT   11   17   24                                                       
CONECT   12   15   31                                                       
CONECT   13    1   15   19                                                  
CONECT   14   10   19   20                                                  
CONECT   15   12   13   18                                                  
CONECT   16   10   23   24                                                  
CONECT   17   11   26   27                                                  
CONECT   18   15   20   21                                                  
CONECT   19   13   14   32                                                  
CONECT   20   14   18   29                                                  
CONECT   21   18   28   31                                                  
CONECT   22    2    3   26   33                                             
CONECT   23    4    8   16   26                                             
CONECT   24    5   11   16   32                                             
CONECT   25    9   30   33   34                                             
CONECT   26   17   22   23   34                                             
CONECT   27   17                                                            
CONECT   28   21                                                            
CONECT   29    6   20                                                       
CONECT   30    7   25                                                       
CONECT   31   12   21                                                       
CONECT   32   19   24                                                       
CONECT   33   22   25                                                       
CONECT   34   25   26                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Value	Source
2,2,7,7-Tetramethyl-1,6-dioxaspiro[4.4]non-8-ene	HMDB

Chemical Formula

C₂₆H₃₄O₈

Average Mass

474.5434 Da

Monoisotopic Mass

474.22537 Da

IUPAC Name

2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6(14),7,12-trien-11-one

Traditional Name

2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6(14),7,12-trien-11-one

CAS Registry Number

Not Available

SMILES

COC1=C2C(=O)OCC2=C(C)C2=C1CC1C(C)(CC(O)C34OC(CCC13C)(OC)OC4(C)C)O2

InChI Identifier

InChI=1S/C26H34O8/c1-13-15-12-31-21(28)18(15)20(29-6)14-10-16-23(4)8-9-25(30-7)33-22(2,3)26(23,34-25)17(27)11-24(16,5)32-19(13)14/h16-17,27H,8-12H2,1-7H3

InChI Key

ZVFMDVFPBVFGPG-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
Aspergillus ustus	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
Tetrahydrofuran
Dihydrofuran
Oxacycle
Organoheterocyclic 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	2.98	ALOGPS
logP	3.57	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	13.77	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	92.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	122.4 m³·mol⁻¹	ChemAxon
Polarizability	50.17 Å³	ChemAxon
Number of Rings	6	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

HMDB0030006

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001296

KNApSAcK ID

Not Available

Chemspider ID

9074559

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10899299

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6,8(12),13-trien-11-one (NP0308049)

MOL for NP0308049 (2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6,8(12),13-trien-11-one)

3D MOL for NP0308049 (2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6,8(12),13-trien-11-one)

3D SDF for NP0308049 (2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6,8(12),13-trien-11-one)

3D-SDF for NP0308049 (2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6,8(12),13-trien-11-one)

PDB for NP0308049 (2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6,8(12),13-trien-11-one)

3D PDB for NP0308049 (2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6,8(12),13-trien-11-one)

SMILES for NP0308049 (2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6,8(12),13-trien-11-one)

INCHI for NP0308049 (2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6,8(12),13-trien-11-one)

Structure for NP0308049 (2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6,8(12),13-trien-11-one)

3D Structure for NP0308049 (2-hydroxy-13,20-dimethoxy-4,7,17,22,22-pentamethyl-5,10,21,23-tetraoxahexacyclo[18.2.1.0¹,¹⁷.0⁴,¹⁶.0⁶,¹⁴.0⁸,¹²]tricosa-6,8(12),13-trien-11-one)