NP-MRD: Showing NP-Card for 12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate (NP0296327)

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Record Information

Version

2.0

Created at

2022-09-10 05:50:30 UTC

Updated at

2022-09-10 05:50:30 UTC

NP-MRD ID

NP0296327

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate

Description

Jasmolone belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). Jasmolone is an extremely weak basic (essentially neutral) compound (based on its pKa). Lipoxygenase is an iron-containing enzyme that is used to catalyze dioxygenation of polyunsaturated fatty acids in this case, α-linolenic acid. Outside of the human body, Jasmolone has been detected, but not quantified in, herbs and spices and tea. This could make jasmolone a potential biomarker for the consumption of these foods. They can specifically be found in the flower heads of Chrysanthemum cinerariaefolium. Lipooxygenase specifically binds to polyunsaturated fatty acids that have a cis,cis-1,4-pentadiene present. Jasmonic acid is used in the production of secondary metabolites in a plants signaling system. 12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate is found in Aspergillus diversus. Jasmolone is part of the secondary alcohol family.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061304592D          

 36 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 05061304592D          

 36 40  0  0  0  0            999 V2000
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 25 22  1  0  0  0  0
 26 14  1  0  0  0  0
 26 20  1  0  0  0  0
 26 23  1  0  0  0  0
 27 15  1  0  0  0  0
 27 21  1  0  0  0  0
 27 26  1  0  0  0  0
 28 16  2  0  0  0  0
 29 19  2  0  0  0  0
 30 20  2  0  0  0  0
 31 21  2  0  0  0  0
 32 27  1  0  0  0  0
 33 15  1  0  0  0  0
 33 20  1  0  0  0  0
 34 16  1  0  0  0  0
 34 18  1  0  0  0  0
 35 19  1  0  0  0  0
 35 22  1  0  0  0  0
 36 21  1  0  0  0  0
 36 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296327

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(=O)C23C(=C)C(C)(CC4=C(C)C5(C=CC(=O)OC5(C)C)C(CC24C)OC(C)=O)OC(=O)C13O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O9/c1-13-17-11-24(8)14(2)26(20(30)33-15(3)27(26,32)21(31)36-24)23(17,7)12-18(34-16(4)28)25(13)10-9-19(29)35-22(25,5)6/h9-10,15,18,32H,2,11-12H2,1,3-8H3

> <INCHI_KEY>
SLCHGQPSMLGFMX-UHFFFAOYSA-N

> <FORMULA>
C27H32O9

> <MOLECULAR_WEIGHT>
500.5376

> <EXACT_MASS>
500.204632622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
49.86744652344962

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-2,6-dihydro-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
1.7914144636666671

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.789383460988184

> <JCHEM_PKA_STRONGEST_BASIC>
-4.640523674163767

> <JCHEM_POLAR_SURFACE_AREA>
125.43000000000002

> <JCHEM_REFRACTIVITY>
125.21769999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate

> <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       6.855   3.070   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.769   1.166   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.694  -2.908   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.665  -3.886   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.572  -2.261   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.535  -1.626   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.063  -1.368   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.786   3.735   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.352   2.131   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.832   1.880   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.671   2.519   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.229  -1.254   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.313   1.629   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.370   0.861   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.708  -2.272   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.184  -3.635   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.794   1.377   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.749  -1.003   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.329   0.941   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.199  -2.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.083   0.424   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.268  -0.752   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.252  -0.064   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.076   2.223   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.290   0.438   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.631  -0.516   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.015  -0.759   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.161  -4.825   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      11.848   1.193   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.697  -2.357   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -1.595   0.133   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -0.467  -1.176   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.052  -3.039   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       7.726  -2.193   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       9.787  -0.500   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.489   1.908   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   16                                                            
CONECT    5   22                                                            
CONECT    6   22                                                            
CONECT    7   23                                                            
CONECT    8   24                                                            
CONECT    9   10   19                                                       
CONECT   10    9   25                                                       
CONECT   11   17   24                                                       
CONECT   12   18   23                                                       
CONECT   13    1   17   25                                                  
CONECT   14    2   24   26                                                  
CONECT   15    3   27   33                                                  
CONECT   16    4   28   34                                                  
CONECT   17   11   13   23                                                  
CONECT   18   12   25   34                                                  
CONECT   19    9   29   35                                                  
CONECT   20   26   30   33                                                  
CONECT   21   27   31   36                                                  
CONECT   22    5    6   25   35                                             
CONECT   23    7   12   17   26                                             
CONECT   24    8   11   14   36                                             
CONECT   25   10   13   18   22                                             
CONECT   26   14   20   23   27                                             
CONECT   27   15   21   26   32                                             
CONECT   28   16                                                            
CONECT   29   19                                                            
CONECT   30   20                                                            
CONECT   31   21                                                            
CONECT   32   27                                                            
CONECT   33   15   20                                                       
CONECT   34   16   18                                                       
CONECT   35   19   22                                                       
CONECT   36   21   24                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-3-methyl-2-(2-pentenyl)-2-cyclopenten-1-one, 9ci	HMDB
Jasmololone	HMDB
5-(Acetyloxy)-17-de(acetyloxy)austin, 9ci	HMDB
12'-Hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-2,6-dihydro-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetic acid	Generator

Chemical Formula

C₂₇H₃₂O₉

Average Mass

500.5376 Da

Monoisotopic Mass

500.20463 Da

IUPAC Name

12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-2,6-dihydro-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate

Traditional Name

12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate

CAS Registry Number

Not Available

SMILES

CC1OC(=O)C23C(=C)C(C)(CC4=C(C)C5(C=CC(=O)OC5(C)C)C(CC24C)OC(C)=O)OC(=O)C13O

InChI Identifier

InChI=1S/C27H32O9/c1-13-17-11-24(8)14(2)26(20(30)33-15(3)27(26,32)21(31)36-24)23(17,7)12-18(34-16(4)28)25(13)10-9-19(29)35-22(25,5)6/h9-10,15,18,32H,2,11-12H2,1,3-8H3

InChI Key

SLCHGQPSMLGFMX-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 diversus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Secondary alcohols

Alternative Parents

Substituents

Cyclic ketone
Secondary alcohol
Ketone
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	2.55	ALOGPS
logP	1.79	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	10.79	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	125.22 m³·mol⁻¹	ChemAxon
Polarizability	49.87 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030039

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001341

KNApSAcK ID

Not Available

Chemspider ID

4524423

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Jasmolone

METLIN ID

Not Available

PubChem Compound

5374699

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate (NP0296327)

MOL for NP0296327 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate)

3D MOL for NP0296327 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate)

3D SDF for NP0296327 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate)

3D-SDF for NP0296327 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate)

PDB for NP0296327 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate)

3D PDB for NP0296327 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate)

SMILES for NP0296327 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate)

INCHI for NP0296327 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate)

Structure for NP0296327 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate)

3D Structure for NP0296327 (12'-hydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-6,11',15'-trioxo-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-en-4'-yl acetate)