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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:39:44 UTC

Update Date

2023-02-21 17:24:51 UTC

HMDB ID

HMDB0035652

Secondary Accession Numbers

HMDB35652

Metabolite Identification

Common Name

Perilla sugar

Description

Perilla sugar belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review a small amount of articles have been published on Perilla sugar.

Structure

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

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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    5    9                                                       
CONECT    4    6    9                                                       
CONECT    5    3   10                                                       
CONECT    6    4   10                                                       
CONECT    7    9   11                                                       
CONECT    8    1    2   10                                                  
CONECT    9    3    4    7                                                  
CONECT   10    5    6    8                                                  
CONECT   11    7   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0035652
HETATM    1  C1  UNL     1      -2.764   1.575   0.908  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.367   0.388   0.484  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.399  -0.605   0.092  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.939   0.041   0.395  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.063   1.185   0.858  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.345   0.786   0.724  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.817  -0.144  -0.087  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.249  -0.441  -0.118  1.00  0.00           C  
HETATM    9  N1  UNL     1       3.735  -1.331  -0.889  1.00  0.00           N  
HETATM   10  O1  UNL     1       5.096  -1.628  -0.933  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.884  -0.878  -0.960  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.495  -0.320  -1.007  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.818   1.811   0.966  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.048   2.347   1.211  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.146  -1.079  -0.856  1.00  0.00           H  
HETATM   16  H4  UNL     1      -3.528  -1.354   0.926  1.00  0.00           H  
HETATM   17  H5  UNL     1      -4.391  -0.098  -0.062  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.684  -0.831   1.038  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.261   1.450   1.914  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.313   2.057   0.184  1.00  0.00           H  
HETATM   21  H9  UNL     1       2.094   1.298   1.351  1.00  0.00           H  
HETATM   22  H10 UNL     1       3.914   0.109   0.530  1.00  0.00           H  
HETATM   23  H11 UNL     1       5.728  -0.885  -1.254  1.00  0.00           H  
HETATM   24  H12 UNL     1       0.807  -1.941  -0.611  1.00  0.00           H  
HETATM   25  H13 UNL     1       1.330  -0.924  -1.977  1.00  0.00           H  
HETATM   26  H14 UNL     1      -0.608   0.534  -1.703  1.00  0.00           H  
HETATM   27  H15 UNL     1      -1.174  -1.123  -1.378  1.00  0.00           H  
CONECT    1    2    2   13   14
CONECT    2    3    4
CONECT    3   15   16   17
CONECT    4    5   12   18
CONECT    5    6   19   20
CONECT    6    7    7   21
CONECT    7    8   11
CONECT    8    9    9   22
CONECT    9   10
CONECT   10   23
CONECT   11   12   24   25
CONECT   12   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Cyclohexene-1-carboxaldehyde, 4-isopropenyl-, anti-oxime	HMDB
1-Perillaldehyde alpha -antioxime	HMDB
4-Isopropenyl-1-cyclohexene-1-carbaldehyde oxime	HMDB
4-Isopropenyl-1-cyclohexene-1-carboxaldehyde, anti-oxime	HMDB
L-Perillaldehyde alpha -syn-oxime	HMDB
Perillartine	HMDB
Perillartine, (e)-(+)-isomer	MeSH
Perillartine, (e)-(-)-isomer	MeSH
Perillartine, (S)-isomer	MeSH
Perillartine, (e)-(+-)-isomer	MeSH
Perillartine, (e)-isomer	MeSH

Chemical Formula

C₁₀H₁₅NO

Average Molecular Weight

165.2322

Monoisotopic Molecular Weight

165.115364107

IUPAC Name

(E)-N-{[4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methylidene}hydroxylamine

Traditional Name

perillartine

CAS Registry Number

30950-27-7

SMILES

CC(=C)C1CCC(\C=N\O)=CC1

InChI Identifier

InChI=1S/C10H15NO/c1-8(2)10-5-3-9(4-6-10)7-11-12/h3,7,10,12H,1,4-6H2,2H3/b11-7+

InChI Key

XCOJIVIDDFTHGB-YRNVUSSQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclohexene oxime
Aldoxime
Oxime
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035652)

Source

Endogenous

Endogenous (HMDB: HMDB0035652)

Animal

Animal (HMDB: HMDB0035652)

Exogenous

Food

Food (HMDB: HMDB0035652)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035652)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035652)

Lipid metabolism pathway (HMDB: HMDB0035652)

Cellular process

Cell signaling (HMDB: HMDB0035652)

Biochemical process

Lipid transport (HMDB: HMDB0035652)

Role

Biological role

Energy source (HMDB: HMDB0035652)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035652)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	102 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	3.13	ALOGPS
logP	2.26	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.47	ChemAxon
pKa (Strongest Basic)	3.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	51.09 m³·mol⁻¹	ChemAxon
Polarizability	19.01 Å³	ChemAxon
Number of Rings	1	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]+	140.143	31661259
DarkChem	[M-H]-	135.286	31661259
DeepCCS	[M+H]+	137.935	30932474
DeepCCS	[M-H]-	135.377	30932474
DeepCCS	[M-2H]-	171.751	30932474
DeepCCS	[M+Na]+	147.087	30932474
AllCCS	[M+H]+	137.5	32859911
AllCCS	[M+H-H2O]+	133.1	32859911
AllCCS	[M+NH4]+	141.5	32859911
AllCCS	[M+Na]+	142.6	32859911
AllCCS	[M-H]-	139.8	32859911
AllCCS	[M+Na-2H]-	141.1	32859911
AllCCS	[M+HCOO]-	142.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Perilla sugar	CC(=C)C1CCC(\C=N\O)=CC1	2043.8	Standard polar	33892256
Perilla sugar	CC(=C)C1CCC(\C=N\O)=CC1	1475.4	Standard non polar	33892256
Perilla sugar	CC(=C)C1CCC(\C=N\O)=CC1	1492.1	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 - Perilla sugar GC-MS (Non-derivatized) - 70eV, Positive	splash10-00nf-9400000000-8aff2a750795bd7b2876	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Perilla sugar GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Perilla sugar 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 - Perilla sugar 10V, Positive-QTOF	splash10-014i-0900000000-0b74eaa9a5ff0ff8f99a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perilla sugar 20V, Positive-QTOF	splash10-001i-2900000000-c7519633a2ec4b8f2f9d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perilla sugar 40V, Positive-QTOF	splash10-0gb9-9100000000-f0d165dfde63edaa0dc5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perilla sugar 10V, Negative-QTOF	splash10-03di-0900000000-fb3b7610c07ff17aafa7	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perilla sugar 20V, Negative-QTOF	splash10-03di-1900000000-d4e94cea5a99cb54e91c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perilla sugar 40V, Negative-QTOF	splash10-00kb-3900000000-ddf4b2b51cb29961977b	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perilla sugar 10V, Negative-QTOF	splash10-03di-0900000000-5a67776f4d9f6897ce74	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perilla sugar 20V, Negative-QTOF	splash10-01q9-0900000000-4cabc63cc2fffab3f4d4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perilla sugar 40V, Negative-QTOF	splash10-0006-9300000000-f4e28bb1532e4d3cc011	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perilla sugar 10V, Positive-QTOF	splash10-014i-0900000000-359b57aaba4b2771db78	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perilla sugar 20V, Positive-QTOF	splash10-000x-4900000000-e93ee7be79807f791048	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perilla sugar 40V, Positive-QTOF	splash10-0036-9200000000-66ef1f7a764f6b7ecbda	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX 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

FDB014365

KNApSAcK ID

Not Available

Chemspider ID

4517728

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Perillaldehyde

METLIN ID

Not Available

PubChem Compound

5365782

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Perilla sugar (HMDB0035652)

MOL for HMDB0035652 (Perilla sugar)

3D MOL for HMDB0035652 (Perilla sugar)

3D SDF for HMDB0035652 (Perilla sugar)

3D-SDF for HMDB0035652 (Perilla sugar)

PDB for HMDB0035652 (Perilla sugar)

3D PDB for HMDB0035652 (Perilla sugar)

SMILES for HMDB0035652 (Perilla sugar)

INCHI for HMDB0035652 (Perilla sugar)

Structure for HMDB0035652 (Perilla sugar)

3D Structure for HMDB0035652 (Perilla sugar)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra