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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:49:11 UTC

Update Date

2022-03-07 02:54:16 UTC

HMDB ID

HMDB0034889

Secondary Accession Numbers

HMDB34889

Metabolite Identification

Common Name

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

Description

3alpha,4,7,7alpha-Tetrahydro-4-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,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione has been detected, but not quantified in, milk and milk products. This could make 3alpha,4,7,7alpha-tetrahydro-4-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,4,7,7alpha-Tetrahydro-4-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      -2.516   0.586   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.516  -0.956   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.182  -1.727   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.149  -0.956   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.149   0.586   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.182   1.354   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.614  -1.431   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.516  -0.185   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.614   1.056   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.092   2.521   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.092  -2.896   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.182   2.896   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    1    5   12                                                  
CONECT    7    4    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    5    8   10                                                  
CONECT   10    9                                                            
CONECT   11    7                                                            
CONECT   12    6                                                            
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,4,7,7a-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione	Generator
3Α,4,7,7α-tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione	Generator
1,2,3,6-tetrahydro-3-Hydroxyphthalimide	HMDB

Chemical Formula

C₈H₉NO₃

Average Molecular Weight

167.162

Monoisotopic Molecular Weight

167.058243159

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC1C=CCC2C1C(=O)NC2=O

InChI Identifier

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

InChI Key

MLJWDNXRMUBJJU-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
Pyrroline
Secondary alcohol
N-acylimine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Alcohol
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0244288)

Biofluid or Excreta

Non-excretory biofluid

Blood (PMID: 31557052)

Process

Not Available

Role

Biological role

metabolite (HMDB: HMDB0244288)

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	217 g/L	ALOGPS
logP	-0.39	ALOGPS
logP	-0.92	ChemAxon
logS	0.11	ALOGPS
pKa (Strongest Acidic)	10.09	ChemAxon
pKa (Strongest Basic)	-3.1	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	41.31 m³·mol⁻¹	ChemAxon
Polarizability	15.55 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]+	136.536	31661259
DarkChem	[M-H]-	133.405	31661259
DeepCCS	[M+H]+	132.672	30932474
DeepCCS	[M-H]-	129.247	30932474
DeepCCS	[M-2H]-	166.679	30932474
DeepCCS	[M+Na]+	141.728	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione	OC1C=CCC2C1C(=O)NC2=O	3142.5	Standard polar	33892256
3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione	OC1C=CCC2C1C(=O)NC2=O	1588.0	Standard non polar	33892256
3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione	OC1C=CCC2C1C(=O)NC2=O	1761.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione,1TMS,isomer #1	C[Si](C)(C)OC1C=CCC2C(=O)NC(=O)C12	1792.8	Semi standard non polar	33892256
3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione,1TMS,isomer #2	C[Si](C)(C)N1C(=O)C2CC=CC(O)C2C1=O	1699.3	Semi standard non polar	33892256
3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione,2TMS,isomer #1	C[Si](C)(C)OC1C=CCC2C(=O)N([Si](C)(C)C)C(=O)C12	1791.3	Semi standard non polar	33892256
3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione,2TMS,isomer #1	C[Si](C)(C)OC1C=CCC2C(=O)N([Si](C)(C)C)C(=O)C12	1728.5	Standard non polar	33892256
3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=CCC2C(=O)NC(=O)C12	2032.7	Semi standard non polar	33892256
3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)C2CC=CC(O)C2C1=O	1940.4	Semi standard non polar	33892256
3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=CCC2C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C12	2238.6	Semi standard non polar	33892256
3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=CCC2C(=O)N([Si](C)(C)C(C)(C)C)C(=O)C12	2188.8	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,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-8900000000-22dfe71e7ae98a016058	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-9630000000-0a8a836a2c1abd182eba	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha,4,7,7alpha-Tetrahydro-4-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,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione 10V, Positive-QTOF	splash10-0uxr-0900000000-2d45e08f7d6290954308	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione 20V, Positive-QTOF	splash10-0uxr-3900000000-5f05e4e9532c2c88f68a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione 40V, Positive-QTOF	splash10-0udl-9400000000-6014e90e816e2054ed70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione 10V, Negative-QTOF	splash10-014i-0900000000-f165e280feaed788cf4d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione 20V, Negative-QTOF	splash10-00kb-7900000000-b8013b95abf5a3e1be32	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione 40V, Negative-QTOF	splash10-0006-9100000000-346a8e648325dd7abfc3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione 10V, Negative-QTOF	splash10-014i-0900000000-54ab2df4743f6d0ea000	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione 20V, Negative-QTOF	splash10-014m-5900000000-f3dae057be31e08cdd14	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione 40V, Negative-QTOF	splash10-0006-9200000000-8c7f30426b820fbc4f33	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione 10V, Positive-QTOF	splash10-014i-0900000000-02f8857feda43cbfeef2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione 20V, Positive-QTOF	splash10-0udi-1900000000-6961f31dae12cc01783f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione 40V, Positive-QTOF	splash10-0f97-9300000000-9541c027eb5ade49cd69	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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

FDB013465

KNApSAcK ID

Not Available

Chemspider ID

35013793

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86242667

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,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione (HMDB0034889)

MOL for HMDB0034889 (3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione)

3D MOL for HMDB0034889 (3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione)

3D SDF for HMDB0034889 (3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione)

3D-SDF for HMDB0034889 (3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione)

PDB for HMDB0034889 (3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione)

3D PDB for HMDB0034889 (3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione)

SMILES for HMDB0034889 (3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione)

INCHI for HMDB0034889 (3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione)

Structure for HMDB0034889 (3alpha,4,7,7alpha-Tetrahydro-4-hydroxy-1H-isoindole-1,3(2H)-dione)

3D Structure for HMDB0034889 (3alpha,4,7,7alpha-Tetrahydro-4-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