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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:49:05 UTC

Update Date

2022-03-07 02:54:16 UTC

HMDB ID

HMDB0034887

Secondary Accession Numbers

HMDB34887

Metabolite Identification

Common Name

3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione

Description

3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione has been detected, but not quantified in, milk and milk products. This could make 3alpha,4,5,7alpha-tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione.

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      -1.848   0.774   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.848  -0.768   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.514  -1.539   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.817  -0.768   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.817   0.774   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.514   1.542   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.282  -1.244   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.184   0.003   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.282   1.244   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.760   2.708   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.760  -2.708   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.184  -1.539   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    5    8   10                                                  
CONECT   10    9                                                            
CONECT   11    7                                                            
CONECT   12    2                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3a,4,5,7a-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione	Generator
3Α,4,5,7α-tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione	Generator
1,2,3,4-tetrahydro-4-Hydroxyphthalimide	HMDB

Chemical Formula

C₈H₉NO₃

Average Molecular Weight

167.162

Monoisotopic Molecular Weight

167.058243159

IUPAC Name

5-hydroxy-2,3,3a,4,5,7a-hexahydro-1H-isoindole-1,3-dione

Traditional Name

5-hydroxy-3a,4,5,7a-tetrahydro-2H-isoindole-1,3-dione

CAS Registry Number

Not Available

SMILES

OC1CC2C(C=C1)C(=O)NC2=O

InChI Identifier

InChI=1S/C8H9NO3/c10-4-1-2-5-6(3-4)8(12)9-7(5)11/h1-2,4-6,10H,3H2,(H,9,11,12)

InChI Key

GNUDNAYOODXBQP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

Alternative Parents

Substituents

Isoindolone
Isoindole
2-pyrrolidone
Pyrrolidone
Carboxylic acid imide
Dicarboximide
Carboxylic acid imide, n-unsubstituted
Pyrrolidine
Lactam
Secondary alcohol
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Organonitrogen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034887)
Cytoplasm (HMDB: HMDB0034887)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034887)

Source

Exogenous

Exogenous (HMDB: HMDB0034887)

Food

Food (HMDB: HMDB0034887)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Endogenous

Animal

Animal (HMDB: HMDB0034887)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034887)

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	119 g/L	ALOGPS
logP	-0.56	ALOGPS
logP	-1.1	ChemAxon
logS	-0.15	ALOGPS
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.46 m³·mol⁻¹	ChemAxon
Polarizability	15.45 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	136.661	31661259
DarkChem	[M-H]-	132.261	31661259
DeepCCS	[M+H]+	133.225	30932474
DeepCCS	[M-H]-	129.679	30932474
DeepCCS	[M-2H]-	167.165	30932474
DeepCCS	[M+Na]+	142.303	30932474
AllCCS	[M+H]+	136.7	32859911
AllCCS	[M+H-H2O]+	132.3	32859911
AllCCS	[M+NH4]+	140.9	32859911
AllCCS	[M+Na]+	142.0	32859911
AllCCS	[M-H]-	133.8	32859911
AllCCS	[M+Na-2H]-	134.5	32859911
AllCCS	[M+HCOO]-	135.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione	OC1CC2C(C=C1)C(=O)NC2=O	3340.5	Standard polar	33892256
3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione	OC1CC2C(C=C1)C(=O)NC2=O	1615.8	Standard non polar	33892256
3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione	OC1CC2C(C=C1)C(=O)NC2=O	1765.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione,1TMS,isomer #1	C[Si](C)(C)OC1C=CC2C(=O)NC(=O)C2C1	1821.2	Semi standard non polar	33892256
3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione,1TMS,isomer #2	C[Si](C)(C)N1C(=O)C2C=CC(O)CC2C1=O	1744.8	Semi standard non polar	33892256
3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione,2TMS,isomer #1	C[Si](C)(C)OC1C=CC2C(=O)N([Si](C)(C)C)C(=O)C2C1	1830.6	Semi standard non polar	33892256
3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione,2TMS,isomer #1	C[Si](C)(C)OC1C=CC2C(=O)N([Si](C)(C)C)C(=O)C2C1	1758.3	Standard non polar	33892256
3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=CC2C(=O)NC(=O)C2C1	2062.8	Semi standard non polar	33892256
3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)C2C=CC(O)CC2C1=O	1991.0	Semi standard non polar	33892256
3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=CC2C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C2C1	2288.1	Semi standard non polar	33892256
3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=CC2C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C2C1	2194.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-00g0-5900000000-40f039d75210363130a6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-6910000000-e6c740df305527725d99	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione 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 - 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione 10V, Positive-QTOF	splash10-0uxr-0900000000-162cfd7443f05218fb27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione 20V, Positive-QTOF	splash10-0uxr-1900000000-333dfbbe6b2e10f4a2f9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione 40V, Positive-QTOF	splash10-0udi-9400000000-580a593c1152cc5753af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione 10V, Negative-QTOF	splash10-014i-0900000000-1aca7af3b184936c0d86	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione 20V, Negative-QTOF	splash10-014j-2900000000-f208b8f4fbb061f55bf2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione 40V, Negative-QTOF	splash10-0006-9100000000-b2b7d811faa3d8b3749f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione 10V, Positive-QTOF	splash10-0uxr-0900000000-1096f24c2ecaa5e49fd8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione 20V, Positive-QTOF	splash10-014i-2900000000-8a6c108282d18377d6d4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione 40V, Positive-QTOF	splash10-004j-9300000000-ec714d1df0faa8f6ad29	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione 10V, Negative-QTOF	splash10-014i-0900000000-1336866b7de76e43839f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione 20V, Negative-QTOF	splash10-014l-6900000000-58d6bd4a5026fdd03380	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione 40V, Negative-QTOF	splash10-0006-9200000000-8b8b46d6fc271364879c	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)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart 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

FDB013463

KNApSAcK ID

Not Available

Chemspider ID

35013792

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

130791563

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

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

Showing metabocard for 3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione (HMDB0034887)

MOL for HMDB0034887 (3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione)

3D MOL for HMDB0034887 (3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione)

3D SDF for HMDB0034887 (3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione)

3D-SDF for HMDB0034887 (3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione)

PDB for HMDB0034887 (3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione)

3D PDB for HMDB0034887 (3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione)

SMILES for HMDB0034887 (3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione)

INCHI for HMDB0034887 (3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione)

Structure for HMDB0034887 (3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione)

3D Structure for HMDB0034887 (3alpha,4,5,7alpha-Tetrahydro-5-hydroxy-1H-isoindole-1,3(2H)-dione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra