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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:36:34 UTC

Update Date

2023-02-21 17:24:50 UTC

HMDB ID

HMDB0035600

Secondary Accession Numbers

HMDB35600

Metabolite Identification

Common Name

(S)-Phellandral

Description

(S)-Phellandral 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 (S)-Phellandral.

Structure

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

COMPND    HMDB0035600
HETATM    1  C1  UNL     1      -2.670  -0.503  -0.955  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.776  -0.019   0.155  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.357  -0.534   1.457  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.364  -0.550   0.040  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.411   0.008   1.202  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.859  -0.108   1.075  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.421   0.078  -0.100  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.885  -0.031  -0.264  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.653  -0.303   0.692  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.583   0.397  -1.248  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.268  -0.324  -1.287  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.564  -1.588  -1.046  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.526   0.041  -1.905  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.720  -0.305  -0.647  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.706   1.086   0.136  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.386  -0.949   1.316  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.759  -1.328   1.908  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.453   0.280   2.202  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.441  -1.646   0.204  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.094  -0.485   2.145  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.179   1.102   1.361  1.00  0.00           H  
HETATM   22  H11 UNL     1       2.474  -0.348   1.953  1.00  0.00           H  
HETATM   23  H12 UNL     1       4.333   0.124  -1.233  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.162   0.211  -2.176  1.00  0.00           H  
HETATM   25  H14 UNL     1       1.403   1.512  -1.234  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.421   0.297  -1.896  1.00  0.00           H  
HETATM   27  H16 UNL     1       0.420  -1.265  -1.857  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   15
CONECT    3   16   17   18
CONECT    4    5   11   19
CONECT    5    6   20   21
CONECT    6    7    7   22
CONECT    7    8   10
CONECT    8    9    9   23
CONECT   10   11   24   25
CONECT   11   26   27
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

4-(propan-2-yl)cyclohex-1-ene-1-carbaldehyde

Traditional Name

4-isopropylcyclohex-1-ene-1-carbaldehyde

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7-8,10H,4-6H2,1-2H3

InChI Key

AEVLWICMAHGAMS-UHFFFAOYSA-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
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

an aldehyde (CPD-12467 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035600)

Source

Endogenous

Endogenous (HMDB: HMDB0035600)

Plant

Plant (HMDB: HMDB0035600)

Animal

Animal (HMDB: HMDB0035600)

Exogenous

Food

Food (HMDB: HMDB0035600)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035600)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035600)

Lipid metabolism pathway (HMDB: HMDB0035600)

Cellular process

Cell signaling (HMDB: HMDB0035600)

Biochemical process

Lipid transport (HMDB: HMDB0035600)

Role

Biological role

Energy source (HMDB: HMDB0035600)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035600)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	2.9	ALOGPS
logP	2.6	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.49 m³·mol⁻¹	ChemAxon
Polarizability	18.39 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	135.216	31661259
DarkChem	[M-H]-	130.526	31661259
DeepCCS	[M+H]+	137.722	30932474
DeepCCS	[M-H]-	134.242	30932474
DeepCCS	[M-2H]-	171.78	30932474
DeepCCS	[M+Na]+	146.997	30932474
AllCCS	[M+H]+	133.7	32859911
AllCCS	[M+H-H2O]+	129.3	32859911
AllCCS	[M+NH4]+	137.9	32859911
AllCCS	[M+Na]+	139.0	32859911
AllCCS	[M-H]-	138.7	32859911
AllCCS	[M+Na-2H]-	140.2	32859911
AllCCS	[M+HCOO]-	142.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-Phellandral	CC(C)C1CCC(C=O)=CC1	1731.0	Standard polar	33892256
(S)-Phellandral	CC(C)C1CCC(C=O)=CC1	1248.1	Standard non polar	33892256
(S)-Phellandral	CC(C)C1CCC(C=O)=CC1	1282.5	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 - (S)-Phellandral GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9600000000-51c8c64f4aadb3de1654	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Phellandral 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 - (S)-Phellandral 10V, Positive-QTOF	splash10-0udi-1900000000-e6d4928798e0fbf85b5a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Phellandral 20V, Positive-QTOF	splash10-0udi-8900000000-2faba57dc0dff652f554	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Phellandral 40V, Positive-QTOF	splash10-0le9-9100000000-3e795ba54762478edb08	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Phellandral 10V, Negative-QTOF	splash10-0udi-0900000000-481ae35d244f72f5b50d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Phellandral 20V, Negative-QTOF	splash10-0udi-0900000000-afc59784ba5d79732d85	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Phellandral 40V, Negative-QTOF	splash10-0v59-6900000000-cf921b4cc96ccbc7c23c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Phellandral 10V, Positive-QTOF	splash10-0gvo-6900000000-b7e8dfbcd733b8d0e96f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Phellandral 20V, Positive-QTOF	splash10-0006-9200000000-0153e1eabb27b79709d0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Phellandral 40V, Positive-QTOF	splash10-00kf-9000000000-c43ecc870823be08e578	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Phellandral 10V, Negative-QTOF	splash10-0fk9-0900000000-ac2b64fa7924ab40726b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Phellandral 20V, Negative-QTOF	splash10-0kmi-0900000000-553bfae0e33d06adfa8c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Phellandral 40V, Negative-QTOF	splash10-016r-9300000000-e261c6c4a7985bcc44bc	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+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

FDB014293

KNApSAcK ID

C00053672

Chemspider ID

80763

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

89488

PDB ID

Not Available

ChEBI ID

167401

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 (S)-Phellandral (HMDB0035600)

MOL for HMDB0035600 ((S)-Phellandral)

3D MOL for HMDB0035600 ((S)-Phellandral)

3D SDF for HMDB0035600 ((S)-Phellandral)

3D-SDF for HMDB0035600 ((S)-Phellandral)

PDB for HMDB0035600 ((S)-Phellandral)

3D PDB for HMDB0035600 ((S)-Phellandral)

SMILES for HMDB0035600 ((S)-Phellandral)

INCHI for HMDB0035600 ((S)-Phellandral)

Structure for HMDB0035600 ((S)-Phellandral)

3D Structure for HMDB0035600 ((S)-Phellandral)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra