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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:47:14 UTC

Update Date

2022-03-07 02:54:37 UTC

HMDB ID

HMDB0035766

Secondary Accession Numbers

HMDB35766

Metabolite Identification

Common Name

Ascaridole

Description

Ascaridole is found in cardamom. Said to be the major constituent of oil of Peumus boldus (boldo).Ascaridole is a natural organic compound classified as a bicyclic monoterpene that has an unusual bridging peroxide functional group. It is the primary constituent of the oil of Mexican Tea (Dysphania ambrosioides, formerly Chenopodium ambrosioides). It is a colorless liquid that is soluble in most organic solvents. Like other low molecular weight organic peroxides, it is unstable and prone to explosion when heated or treated with organic acids

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.781  -2.264   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.703  -1.561   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.858   0.078   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.234  -0.546   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.015  -1.718   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.186  -1.171   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.514  -1.952   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.625   0.781   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.186   0.312   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.514  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.186   0.703   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.264   2.264   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8   11                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7    9                                             
CONECT    7    6                                                            
CONECT    8    3    9                                                       
CONECT    9    6    8                                                       
CONECT   10   11                                                            
CONECT   11    3   10   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

COMPND    HMDB0035766
HETATM    1  C1  UNL     1      -2.459   0.352  -1.036  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.963  -0.262   0.279  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.619   0.455   1.405  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.488  -0.216   0.265  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.055   1.183   0.150  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.398   1.208   0.164  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.989  -0.179   0.273  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.461  -0.107   0.418  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.567  -0.895  -1.002  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.038  -0.983  -0.931  1.00  0.00           C  
HETATM   11  O1  UNL     1       1.390  -0.823   1.323  1.00  0.00           O  
HETATM   12  O2  UNL     1       0.110  -0.765   1.388  1.00  0.00           O  
HETATM   13  H1  UNL     1      -2.566  -0.401  -1.819  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.734   1.125  -1.316  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.483   0.779  -0.855  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.324  -1.309   0.261  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.752   1.553   1.227  1.00  0.00           H  
HETATM   18  H6  UNL     1      -3.661   0.033   1.508  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.131   0.297   2.385  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.566   2.064   0.067  1.00  0.00           H  
HETATM   21  H9  UNL     1       2.001   2.089   0.106  1.00  0.00           H  
HETATM   22  H10 UNL     1       3.840  -0.996   0.971  1.00  0.00           H  
HETATM   23  H11 UNL     1       3.920  -0.095  -0.608  1.00  0.00           H  
HETATM   24  H12 UNL     1       3.781   0.822   0.906  1.00  0.00           H  
HETATM   25  H13 UNL     1       1.991  -1.919  -0.995  1.00  0.00           H  
HETATM   26  H14 UNL     1       1.889  -0.312  -1.879  1.00  0.00           H  
HETATM   27  H15 UNL     1      -0.416  -0.643  -1.872  1.00  0.00           H  
HETATM   28  H16 UNL     1      -0.269  -2.056  -0.784  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    4   16
CONECT    3   17   18   19
CONECT    4    5   10   12
CONECT    5    6    6   20
CONECT    6    7   21
CONECT    7    8    9   11
CONECT    8   22   23   24
CONECT    9   10   25   26
CONECT   10   27   28
CONECT   11   12
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,4-Epidioxy-p-menth-2-ene	ChEBI
1,4-Peroxido-p-menthene-2	ChEBI
1,4-Peroxy-p-menth-2-ene	ChEBI
1-Isopropyl-4-methyl-2,3-dioxabicyclo[2.2.2]oct-5-ene	ChEBI
1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene	ChEBI
1, 4-Epidioxy-P-menth-2-ene	HMDB
1, 4-Peroxy-P-menth-2-ene	HMDB
1,4-Epidioxy-2-P-menthene	HMDB
1-Isopropyl-4-methyl-2,3-dioxabicyclo(2.2.2)oct-5-ene	HMDB
1-Isopropyl-4-methyl-7-oxabicyclo[2.2.1]hept-2-ene	HMDB
1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo(2.2.2)oct-5-ene	HMDB
1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene, 9ci	HMDB
4-Methyl-1-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene	HMDB
Ascapurin	HMDB
Ascaricum	HMDB
Ascaridiol	HMDB
Ascaridol	HMDB
Ascaridole (organic peroxide)	HMDB
Ascaridole epoxide	HMDB
Ascarisin	HMDB
Askaridol	HMDB
cis-Ascaridole	HMDB
Kebal II	HMDB
Uncinacina	HMDB

Chemical Formula

C₁₀H₁₆O₂

Average Molecular Weight

168.2328

Monoisotopic Molecular Weight

168.115029756

IUPAC Name

1-methyl-4-(propan-2-yl)-2,3-dioxabicyclo[2.2.2]oct-5-ene

Traditional Name

ascaridole

CAS Registry Number

512-85-6

SMILES

CC(C)C12CCC(C)(OO1)C=C2

InChI Identifier

InChI=1S/C10H16O2/c1-8(2)10-6-4-9(3,5-7-10)11-12-10/h4,6,8H,5,7H2,1-3H3

InChI Key

MGYMHQJELJYRQS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-dioxanes. These are organic compounds containing 1,2-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 2.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dioxanes

Sub Class

1,2-dioxanes

Direct Parent

1,2-dioxanes

Alternative Parents

Substituents

Ortho-dioxane
Dialkyl peroxide
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

organic heterobicyclic compound (CHEBI:2866 )
organic peroxide (CHEBI:2866 )
p-menthane monoterpenoid (CHEBI:2866 )
Cyclic monoterpenes (C09836 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035766)

Source

Endogenous

Endogenous (HMDB: HMDB0035766)

Plant

Plant (HMDB: HMDB0035766)

Exogenous

Food

Food (HMDB: HMDB0035766)

Herb and spice

Spice

Cardamom (FooDB: FOOD00074)

Vegetable

Leaf vegetable

Lambsquarters (FooDB: FOOD00394)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0035766)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0035766)

Role

Industrial applicationBiological role

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	3.3 °C	Not Available
Boiling Point	112.00 to 115.00 °C. @ 20.00 mm Hg	The Good Scents Company Information System
Water Solubility	55.5 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.244 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.53 g/L	ALOGPS
logP	2.64	ALOGPS
logP	2.64	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.6 m³·mol⁻¹	ChemAxon
Polarizability	18.93 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.085	31661259
DarkChem	[M-H]-	131.14	31661259
DeepCCS	[M-2H]-	175.22	30932474
DeepCCS	[M+Na]+	150.762	30932474
AllCCS	[M+H]+	134.3	32859911
AllCCS	[M+H-H2O]+	129.8	32859911
AllCCS	[M+NH4]+	138.5	32859911
AllCCS	[M+Na]+	139.7	32859911
AllCCS	[M-H]-	140.0	32859911
AllCCS	[M+Na-2H]-	140.9	32859911
AllCCS	[M+HCOO]-	141.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ascaridole	CC(C)C12CCC(C)(OO1)C=C2	1744.1	Standard polar	33892256
Ascaridole	CC(C)C12CCC(C)(OO1)C=C2	1235.2	Standard non polar	33892256
Ascaridole	CC(C)C12CCC(C)(OO1)C=C2	1249.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ascaridole GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-2900000000-4e6342ba9b29d1dd42ad	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascaridole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ascaridole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascaridole 10V, Positive-QTOF	splash10-014i-0900000000-83d7b2bd24b624b5ea98	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascaridole 20V, Positive-QTOF	splash10-014i-0900000000-1d0d1c7edaaa69d194a1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascaridole 40V, Positive-QTOF	splash10-0udi-0900000000-2c78632dd190511927b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascaridole 10V, Negative-QTOF	splash10-014i-0900000000-177dc272267c0f543701	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascaridole 20V, Negative-QTOF	splash10-014i-0900000000-3317598e1aa469191e58	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascaridole 40V, Negative-QTOF	splash10-0adi-0900000000-fb70c59640ba1c0d01a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascaridole 10V, Negative-QTOF	splash10-014i-0900000000-cb7592114e600c180aec	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascaridole 20V, Negative-QTOF	splash10-014i-0900000000-cb7592114e600c180aec	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascaridole 40V, Negative-QTOF	splash10-014i-0900000000-3a7e13f32c837bc356ac	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascaridole 10V, Positive-QTOF	splash10-014i-0900000000-f9b2951dd69b378c6031	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascaridole 20V, Positive-QTOF	splash10-016r-0900000000-460c95031436dfd1e1b7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ascaridole 40V, Positive-QTOF	splash10-004i-0900000000-6a28e536e83eb1686dba	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ascaridole

METLIN ID

Not Available

PubChem Compound

10545

PDB ID

Not Available

ChEBI ID

2866

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1011381

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Ascaridole (HMDB0035766)

MOL for HMDB0035766 (Ascaridole)

3D MOL for HMDB0035766 (Ascaridole)

3D SDF for HMDB0035766 (Ascaridole)

3D-SDF for HMDB0035766 (Ascaridole)

PDB for HMDB0035766 (Ascaridole)

3D PDB for HMDB0035766 (Ascaridole)

SMILES for HMDB0035766 (Ascaridole)

INCHI for HMDB0035766 (Ascaridole)

Structure for HMDB0035766 (Ascaridole)

3D Structure for HMDB0035766 (Ascaridole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra