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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:02:55 UTC

Update Date

2023-02-21 17:26:42 UTC

HMDB ID

HMDB0038712

Secondary Accession Numbers

HMDB38712

Metabolite Identification

Common Name

(S)-Isosclerone

Description

(S)-Isosclerone belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane (S)-Isosclerone has been detected, but not quantified in, nuts. This could make (S)-isosclerone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (S)-Isosclerone.

Structure

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


  Mrv0541 05061310362D          

 13 14  0  0  0  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  2  1  0  0  0  0
  7  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  3  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038712

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CCC(=O)C2=C1C=CC=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-3,7,11-12H,4-5H2

> <INCHI_KEY>
ZXYYTDCENDYKBR-UHFFFAOYSA-N

> <FORMULA>
C10H10O3

> <MOLECULAR_WEIGHT>
178.1846

> <EXACT_MASS>
178.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
17.823674283477672

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,8-dihydroxy-1,2,3,4-tetrahydronaphthalen-1-one

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
1.3967482796666668

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.325448703108634

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.79664148009184

> <JCHEM_PKA_STRONGEST_BASIC>
-3.144565390501521

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
47.823100000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,8-dihydroxy-3,4-dihydro-2H-naphthalen-1-one

> <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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    8                                                       
CONECT    4    5    7                                                       
CONECT    5    4    9                                                       
CONECT    6    2    7   10                                                  
CONECT    7    4    6   11                                                  
CONECT    8    3   10   12                                                  
CONECT    9    5   10   13                                                  
CONECT   10    6    8    9                                                  
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(4S)-4,8-Dihydroxy-alpha-tetralone	HMDB

Chemical Formula

C₁₀H₁₀O₃

Average Molecular Weight

178.1846

Monoisotopic Molecular Weight

178.062994186

IUPAC Name

4,8-dihydroxy-1,2,3,4-tetrahydronaphthalen-1-one

Traditional Name

4,8-dihydroxy-3,4-dihydro-2H-naphthalen-1-one

CAS Registry Number

54712-38-8

SMILES

OC1CCC(=O)C2=C1C=CC=C2O

InChI Identifier

InChI=1S/C10H10O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-3,7,11-12H,4-5H2

InChI Key

ZXYYTDCENDYKBR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Tetralin
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038712)
Cytoplasm (HMDB: HMDB0038712)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038712)

Source

Exogenous

Food

Food (HMDB: HMDB0038712)

Nut

Nuts (FooDB: FOOD00869)

Endogenous

Plant

Plant (HMDB: HMDB0038712)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038712)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	74 - 76 °C	Not Available
Boiling Point	376.20 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	47850 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.330 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	13.9 g/L	ALOGPS
logP	0.7	ALOGPS
logP	1.4	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	9.8	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	47.82 m³·mol⁻¹	ChemAxon
Polarizability	17.82 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	140.239	31661259
DarkChem	[M-H]-	134.473	31661259
DeepCCS	[M+H]+	133.494	30932474
DeepCCS	[M-H]-	129.665	30932474
DeepCCS	[M-2H]-	167.086	30932474
DeepCCS	[M+Na]+	142.625	30932474
AllCCS	[M+H]+	139.2	32859911
AllCCS	[M+H-H2O]+	134.8	32859911
AllCCS	[M+NH4]+	143.3	32859911
AllCCS	[M+Na]+	144.5	32859911
AllCCS	[M-H]-	136.8	32859911
AllCCS	[M+Na-2H]-	137.3	32859911
AllCCS	[M+HCOO]-	137.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-Isosclerone	OC1CCC(=O)C2=C1C=CC=C2O	2689.1	Standard polar	33892256
(S)-Isosclerone	OC1CCC(=O)C2=C1C=CC=C2O	1815.0	Standard non polar	33892256
(S)-Isosclerone	OC1CCC(=O)C2=C1C=CC=C2O	1765.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-Isosclerone,1TMS,isomer #1	C[Si](C)(C)OC1CCC(=O)C2=C(O)C=CC=C21	1784.6	Semi standard non polar	33892256
(S)-Isosclerone,1TMS,isomer #2	C[Si](C)(C)OC1=CC=CC2=C1C(=O)CCC2O	1845.1	Semi standard non polar	33892256
(S)-Isosclerone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CC2=C1C(=O)CCC2O[Si](C)(C)C	1857.4	Semi standard non polar	33892256
(S)-Isosclerone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CCC(=O)C2=C(O)C=CC=C21	2048.7	Semi standard non polar	33892256
(S)-Isosclerone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)CCC2O	2109.8	Semi standard non polar	33892256
(S)-Isosclerone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)CCC2O[Si](C)(C)C(C)(C)C	2336.7	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)-Isosclerone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0h90-0900000000-28b56937916aada133ec	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Isosclerone GC-MS (2 TMS) - 70eV, Positive	splash10-00di-6292000000-b85d315610b99a36ca73	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Isosclerone 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)-Isosclerone 10V, Positive-QTOF	splash10-03fr-0900000000-94f1d124802a31a68dd0	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Isosclerone 20V, Positive-QTOF	splash10-03di-0900000000-9e6f018768e565995ab8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Isosclerone 40V, Positive-QTOF	splash10-03di-3900000000-d80223fb61a875d0a50e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Isosclerone 10V, Negative-QTOF	splash10-004i-0900000000-2a7a0169b72dbdfc376c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Isosclerone 20V, Negative-QTOF	splash10-004i-0900000000-fc1d2769aa0eab73f805	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Isosclerone 40V, Negative-QTOF	splash10-0007-6900000000-331c549734fd0eefe3df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Isosclerone 10V, Positive-QTOF	splash10-004i-0900000000-d67282facbf063f8a375	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Isosclerone 20V, Positive-QTOF	splash10-004i-1900000000-f9be6fc3161e2892b3f2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Isosclerone 40V, Positive-QTOF	splash10-05gj-3900000000-3ce3021b6411f6ffffb6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Isosclerone 10V, Negative-QTOF	splash10-004i-0900000000-27d78cbf1fad45801162	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Isosclerone 20V, Negative-QTOF	splash10-0a6r-0900000000-28e2fa5566d9fa8998f1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Isosclerone 40V, Negative-QTOF	splash10-0a4i-1900000000-ea641dc3f5f30e1a9606	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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+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

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

FDB018120

KNApSAcK ID

C00031466

Chemspider ID

8617670

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10442251

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1620411

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 (S)-Isosclerone (HMDB0038712)

MOL for HMDB0038712 ((S)-Isosclerone)

3D MOL for HMDB0038712 ((S)-Isosclerone)

3D SDF for HMDB0038712 ((S)-Isosclerone)

3D-SDF for HMDB0038712 ((S)-Isosclerone)

PDB for HMDB0038712 ((S)-Isosclerone)

3D PDB for HMDB0038712 ((S)-Isosclerone)

SMILES for HMDB0038712 ((S)-Isosclerone)

INCHI for HMDB0038712 ((S)-Isosclerone)

Structure for HMDB0038712 ((S)-Isosclerone)

3D Structure for HMDB0038712 ((S)-Isosclerone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra