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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:30:20 UTC

Update Date

2021-09-26 22:58:27 UTC

HMDB ID

HMDB0248259

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Alrestatin

Description

Alrestatin belongs to the class of organic compounds known as isoquinolones and derivatives. These are aromatic polycyclic compounds containing a ketone bearing isoquinoline moiety. Based on a literature review a significant number of articles have been published on Alrestatin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Alrestatin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Alrestatin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

ALR
  Mrv0541 02231215542D          

 19 21  0  0  0  0            999 V2000
   -0.2498   -0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4646    0.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2498    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9643   -0.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2498    1.6494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6788   -0.8256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6788    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4646   -0.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1791   -0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8936   -0.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8936    0.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1791    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2498   -1.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4646   -2.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1791   -1.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9643    0.4119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6788    1.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3932    2.0619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9643    2.0619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  8  2  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  2 12  2  0  0  0  0
  3  5  2  0  0  0  0
  3 16  1  0  0  0  0
  4  6  2  0  0  0  0
  4 16  1  0  0  0  0
  7 16  1  0  0  0  0
  7 17  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 15  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248259

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CN1C(=O)C2=CC=CC3=CC=CC(C1=O)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C14H9NO4/c16-11(17)7-15-13(18)9-5-1-3-8-4-2-6-10(12(8)9)14(15)19/h1-6H,7H2,(H,16,17)

> <INCHI_KEY>
GCUCIFQCGJIRNT-UHFFFAOYSA-N

> <FORMULA>
C14H9NO4

> <MOLECULAR_WEIGHT>
255.2256

> <EXACT_MASS>
255.053157781

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
24.576426479387553

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{2,4-dioxo-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-3-yl}acetic acid

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
1.3845591689999996

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4518326159921635

> <JCHEM_PKA_STRONGEST_BASIC>
-6.613963494984546

> <JCHEM_POLAR_SURFACE_AREA>
74.68

> <JCHEM_REFRACTIVITY>
66.74630000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
alrestatin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ALR                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.466  -1.541   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.867   0.769   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.466   1.539   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.800  -0.771   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.466   3.079   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -3.134  -1.541   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.134   1.539   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.867  -0.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.201  -1.541   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.535  -0.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.535   0.769   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.201   1.539   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.466  -3.081   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.867  -3.851   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.201  -3.081   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -1.800   0.769   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -3.134   3.079   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.467   3.849   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.800   3.849   0.000  0.00  0.00           O+0
CONECT    1    4    8   13                                                  
CONECT    2    3    8   12                                                  
CONECT    3    2    5   16                                                  
CONECT    4    1    6   16                                                  
CONECT    5    3                                                            
CONECT    6    4                                                            
CONECT    7   16   17                                                       
CONECT    8    1    2    9                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    2   11                                                       
CONECT   13    1   14                                                       
CONECT   14   13   15                                                       
CONECT   15    9   14                                                       
CONECT   16    3    4    7                                                  
CONECT   17    7   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0248259
HETATM    1  O1  UNL     1       5.247  -0.185   0.044  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.008  -0.068  -0.099  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.520   0.452  -1.278  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.106  -0.478   0.970  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.710  -0.283   0.659  1.00  0.00           N  
HETATM    6  C3  UNL     1       0.956  -1.314   0.027  1.00  0.00           C  
HETATM    7  O3  UNL     1       1.519  -2.397  -0.259  1.00  0.00           O  
HETATM    8  C4  UNL     1      -0.461  -1.163  -0.308  1.00  0.00           C  
HETATM    9  C5  UNL     1      -1.184  -2.163  -0.919  1.00  0.00           C  
HETATM   10  C6  UNL     1      -2.518  -1.952  -1.205  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.167  -0.779  -0.907  1.00  0.00           C  
HETATM   12  C8  UNL     1      -2.427   0.230  -0.287  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.090   1.404   0.008  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.356   2.401   0.621  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.022   2.251   0.932  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.398   1.073   0.625  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.092   0.028   0.003  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.019   0.929   0.962  1.00  0.00           C  
HETATM   19  O4  UNL     1       1.681   1.834   1.517  1.00  0.00           O  
HETATM   20  H1  UNL     1       3.834   0.216  -2.197  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.340   0.073   1.909  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.239  -1.584   1.118  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.672  -3.077  -1.150  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.099  -2.745  -1.692  1.00  0.00           H  
HETATM   25  H6  UNL     1      -4.220  -0.606  -1.130  1.00  0.00           H  
HETATM   26  H7  UNL     1      -4.153   1.545  -0.232  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.880   3.316   0.849  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.443   3.042   1.418  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   20
CONECT    4    5   21   22
CONECT    5    6   18
CONECT    6    7    7    8
CONECT    8    9   17   17
CONECT    9   10   10   23
CONECT   10   11   24
CONECT   11   12   12   25
CONECT   12   13   17
CONECT   13   14   14   26
CONECT   14   15   27
CONECT   15   16   16   28
CONECT   16   17   18
CONECT   18   19   19
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Alrestatin, sodium salt	MeSH
2-{2,4-dioxo-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(12),5,7,9(13),10-pentaen-3-yl}acetate	Generator

Chemical Formula

C₁₄H₉NO₄

Average Molecular Weight

255.2256

Monoisotopic Molecular Weight

255.053157781

IUPAC Name

2-{2,4-dioxo-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaen-3-yl}acetic acid

Traditional Name

alrestatin

CAS Registry Number

Not Available

SMILES

OC(=O)CN1C(=O)C2=CC=CC3=CC=CC(C1=O)=C23

InChI Identifier

InChI=1S/C14H9NO4/c16-11(17)7-15-13(18)9-5-1-3-8-4-2-6-10(12(8)9)14(15)19/h1-6H,7H2,(H,16,17)

InChI Key

GCUCIFQCGJIRNT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoquinolones and derivatives. These are aromatic polycyclic compounds containing a ketone bearing isoquinoline moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Isoquinolones and derivatives

Direct Parent

Isoquinolones and derivatives

Alternative Parents

Substituents

Isoquinolone
Alpha-amino acid or derivatives
Naphthalene
Carboxylic acid imide, n-substituted
Benzenoid
Carboxylic acid imide
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0248259)

Process

Not Available

Role

Not Available

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
logP	1.95	ALOGPS
logP	1.38	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.75 m³·mol⁻¹	ChemAxon
Polarizability	24.58 Å³	ChemAxon
Number of Rings	3	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
DeepCCS	[M-2H]-	187.893	30932474
DeepCCS	[M+Na]+	163.377	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	151.9	32859911
AllCCS	[M+NH4]+	159.1	32859911
AllCCS	[M+Na]+	160.1	32859911
AllCCS	[M-H]-	157.4	32859911
AllCCS	[M+Na-2H]-	156.8	32859911
AllCCS	[M+HCOO]-	156.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alrestatin	OC(=O)CN1C(=O)C2=CC=CC3=CC=CC(C1=O)=C23	4261.2	Standard polar	33892256
Alrestatin	OC(=O)CN1C(=O)C2=CC=CC3=CC=CC(C1=O)=C23	2048.4	Standard non polar	33892256
Alrestatin	OC(=O)CN1C(=O)C2=CC=CC3=CC=CC(C1=O)=C23	2514.4	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 - Alrestatin GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-3390000000-442371e0fa8a83c7db42	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alrestatin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alrestatin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alrestatin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - Alrestatin 10V, Positive-QTOF	splash10-0a4i-0090000000-7b30555ec522073d53b7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alrestatin 20V, Positive-QTOF	splash10-0a4i-0090000000-e3929b3a54021de43852	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alrestatin 40V, Positive-QTOF	splash10-03di-1090000000-cd2dc1d80eae717883c1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alrestatin 10V, Negative-QTOF	splash10-0udi-0090000000-e53c66fd627f796e4c4d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alrestatin 20V, Negative-QTOF	splash10-0w29-0090000000-417884e34f4b4d64af60	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alrestatin 40V, Negative-QTOF	splash10-0j4i-4190000000-9642697f8b5438639f07	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alrestatin 10V, Positive-QTOF	splash10-0a4i-0090000000-05fbfc464a09dbde22b4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alrestatin 20V, Positive-QTOF	splash10-03di-0090000000-5f78a212bc08de5c58e8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alrestatin 40V, Positive-QTOF	splash10-0a4i-0930000000-d24b7dfca32adf3a77b1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alrestatin 10V, Negative-QTOF	splash10-0udi-0090000000-797688b1e281e06575cc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alrestatin 20V, Negative-QTOF	splash10-03di-0090000000-ee529cc8f829811bdc2d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alrestatin 40V, Negative-QTOF	splash10-08fr-0960000000-9276ed4b3b2aa67ec013	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02020

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2036

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alrestatin

METLIN ID

Not Available

PubChem Compound

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Alrestatin (HMDB0248259)

MOL for HMDB0248259 (Alrestatin)

3D MOL for HMDB0248259 (Alrestatin)

3D SDF for HMDB0248259 (Alrestatin)

3D-SDF for HMDB0248259 (Alrestatin)

PDB for HMDB0248259 (Alrestatin)

3D PDB for HMDB0248259 (Alrestatin)

SMILES for HMDB0248259 (Alrestatin)

INCHI for HMDB0248259 (Alrestatin)

Structure for HMDB0248259 (Alrestatin)

3D Structure for HMDB0248259 (Alrestatin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra