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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:20:25 UTC

Update Date

2023-02-21 17:27:11 UTC

HMDB ID

HMDB0039803

Secondary Accession Numbers

HMDB39803

Metabolite Identification

Common Name

4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone

Description

4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone is a coconut, toasted, and tonka tasting compound. Based on a literature review very few articles have been published on 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone.

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      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   4.620   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   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    3    8                                                       
CONECT    3    2    9                                                       
CONECT    4    5    9                                                       
CONECT    5    4   11                                                       
CONECT    6    8   10                                                       
CONECT    7   10   11                                                       
CONECT    8    1    2    6                                                  
CONECT    9    3    4   10                                                  
CONECT   10    6    7    9                                                  
CONECT   11    5    7   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

COMPND    HMDB0039803
HETATM    1  C1  UNL     1       3.498  -0.477  -0.008  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.021  -0.178  -0.032  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.179  -1.161  -0.279  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.233  -0.824  -0.292  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.167  -1.779  -0.131  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.584  -1.443  -0.143  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.409  -2.366  -0.335  1.00  0.00           O  
HETATM    8  C7  UNL     1      -3.061  -0.054   0.065  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.840   0.744   0.550  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.742   0.546  -0.477  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.306   1.604  -0.410  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.595   1.188   0.220  1.00  0.00           C  
HETATM   13  H1  UNL     1       3.946  -0.031  -0.920  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.899   0.030   0.895  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.668  -1.577   0.015  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.514  -2.186  -0.467  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.858  -2.785   0.006  1.00  0.00           H  
HETATM   18  H6  UNL     1      -3.361   0.404  -0.902  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.830   0.021   0.843  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.548   0.250   1.511  1.00  0.00           H  
HETATM   21  H9  UNL     1      -2.089   1.800   0.697  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.239   0.582  -1.476  1.00  0.00           H  
HETATM   23  H11 UNL     1      -0.113   2.436   0.210  1.00  0.00           H  
HETATM   24  H12 UNL     1       0.491   2.042  -1.413  1.00  0.00           H  
HETATM   25  H13 UNL     1       1.567   1.333   1.340  1.00  0.00           H  
HETATM   26  H14 UNL     1       2.391   1.878  -0.131  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    3   12
CONECT    3    4   16
CONECT    4    5    5   10
CONECT    5    6   17
CONECT    6    7    7    8
CONECT    8    9   18   19
CONECT    9   10   20   21
CONECT   10   11   22
CONECT   11   12   23   24
CONECT   12   25   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,4a,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone	Generator
4,4Α,5,6-tetrahydro-7-methyl-2(3H)-naphthalenone	Generator
FEMA 3715	HMDB

Chemical Formula

C₁₁H₁₄O

Average Molecular Weight

162.2283

Monoisotopic Molecular Weight

162.10446507

IUPAC Name

7-methyl-2,3,4,4a,5,6-hexahydronaphthalen-2-one

Traditional Name

7-methyl-4,4a,5,6-tetrahydro-3H-naphthalen-2-one

CAS Registry Number

34545-88-5

SMILES

CC1=CC2=CC(=O)CCC2CC1

InChI Identifier

InChI=1S/C11H14O/c1-8-2-3-9-4-5-11(12)7-10(9)6-8/h6-7,9H,2-5H2,1H3

InChI Key

NGSXTBFUMNXJDK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0039803)

Exogenous

Food

Food (HMDB: HMDB0039803)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0039803)

Role

Biological role

Energy storage (HMDB: HMDB0039803)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039803)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0039803)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	36.00 to 37.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	305.00 to 306.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	174.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.220 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.01 g/L	ALOGPS
logP	2.01	ALOGPS
logP	2.32	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	19.54	ChemAxon
pKa (Strongest Basic)	-4.7	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	0	ChemAxon
Refractivity	50.97 m³·mol⁻¹	ChemAxon
Polarizability	18.91 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]+	140.51	31661259
DarkChem	[M-H]-	134.557	31661259
DeepCCS	[M+H]+	138.182	30932474
DeepCCS	[M-H]-	135.571	30932474
DeepCCS	[M-2H]-	171.336	30932474
DeepCCS	[M+Na]+	146.61	30932474
AllCCS	[M+H]+	135.4	32859911
AllCCS	[M+H-H2O]+	130.9	32859911
AllCCS	[M+NH4]+	139.7	32859911
AllCCS	[M+Na]+	140.9	32859911
AllCCS	[M-H]-	139.5	32859911
AllCCS	[M+Na-2H]-	140.3	32859911
AllCCS	[M+HCOO]-	141.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone	CC1=CC2=CC(=O)CCC2CC1	2215.8	Standard polar	33892256
4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone	CC1=CC2=CC(=O)CCC2CC1	1439.8	Standard non polar	33892256
4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone	CC1=CC2=CC(=O)CCC2CC1	1499.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone,1TMS,isomer #1	CC1=CC2=CC(O[Si](C)(C)C)=CCC2CC1	1691.3	Semi standard non polar	33892256
4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone,1TMS,isomer #1	CC1=CC2=CC(O[Si](C)(C)C)=CCC2CC1	1609.0	Standard non polar	33892256
4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone,1TBDMS,isomer #1	CC1=CC2=CC(O[Si](C)(C)C(C)(C)C)=CCC2CC1	1922.9	Semi standard non polar	33892256
4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone,1TBDMS,isomer #1	CC1=CC2=CC(O[Si](C)(C)C(C)(C)C)=CCC2CC1	1847.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5d-2900000000-7e5f7fce4b4d54ca3284	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone 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 - 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone 10V, Positive-QTOF	splash10-03di-0900000000-105865e4ccee242a41c8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone 20V, Positive-QTOF	splash10-03di-3900000000-14b87620b688981b0a7f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone 40V, Positive-QTOF	splash10-0uxr-9200000000-658c680137561ee63467	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone 10V, Negative-QTOF	splash10-03di-0900000000-3bd913124c1ba0782750	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone 20V, Negative-QTOF	splash10-03di-0900000000-a7c577a0b1c2cc42e875	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone 40V, Negative-QTOF	splash10-02am-2900000000-f819c12f7c058cba9222	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone 10V, Negative-QTOF	splash10-03di-0900000000-bd5a0b9e0df7744b272c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone 20V, Negative-QTOF	splash10-03di-0900000000-be122099fea6b1c8cd8b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone 40V, Negative-QTOF	splash10-0a4i-0900000000-7ecd9033a403803c2dd8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone 10V, Positive-QTOF	splash10-03di-0900000000-f31b38fed3770188d072	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone 20V, Positive-QTOF	splash10-08fr-1900000000-cbed710e4b9918b420c4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone 40V, Positive-QTOF	splash10-05r3-7900000000-9346a70a1d48285a74ee	2021-09-24	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

Cytoplasm
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

FDB019453

KNApSAcK ID

Not Available

Chemspider ID

55795

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61935

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1037601

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 4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone (HMDB0039803)

MOL for HMDB0039803 (4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone)

3D MOL for HMDB0039803 (4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone)

3D SDF for HMDB0039803 (4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone)

3D-SDF for HMDB0039803 (4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone)

PDB for HMDB0039803 (4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone)

3D PDB for HMDB0039803 (4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone)

SMILES for HMDB0039803 (4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone)

INCHI for HMDB0039803 (4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone)

Structure for HMDB0039803 (4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone)

3D Structure for HMDB0039803 (4,4alpha,5,6-Tetrahydro-7-methyl-2(3H)-naphthalenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra