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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:59:46 UTC

Update Date

2021-09-14 15:02:27 UTC

HMDB ID

HMDB0060793

Secondary Accession Numbers

HMDB60793

Metabolite Identification

Common Name

6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one

Description

6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring. 6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one is a moderately basic compound (based on its pKa). 6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazoquinazolin-2-one is a metabolite of anagrelide. It also has been used in the treatment of chronic myeloid leukemia. Anagrelide is a drug used for the treatment of essential thrombocytosis (ET; essential thrombocythemia), or overproduction of blood platelets.

Structure

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

  Mrv0541 07041311592D          

 17 19  0  0  0  0            999 V2000
    1.5983   -0.4834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.1104    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060793

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1N2CC3=C(Cl)C(Cl)=CC=C3N=C2NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H7Cl2N3O2/c11-5-1-2-6-4(7(5)12)3-15-9(17)8(16)14-10(15)13-6/h1-2,9,17H,3H2,(H,13,14,16)

> <INCHI_KEY>
KAXTUTDKZVOONF-UHFFFAOYSA-N

> <FORMULA>
C10H7Cl2N3O2

> <MOLECULAR_WEIGHT>
272.087

> <EXACT_MASS>
270.991531897

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
24.40594554034212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,7-dichloro-3-hydroxy-1H,2H,3H,5H-imidazolidino[2,1-b]quinazolin-2-one

> <ALOGPS_LOGP>
1.27

> <JCHEM_LOGP>
1.6551911329999995

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.654720455342328

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.36979275603826

> <JCHEM_PKA_STRONGEST_BASIC>
1.8751528730005214

> <JCHEM_POLAR_SURFACE_AREA>
64.93

> <JCHEM_REFRACTIVITY>
64.449

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7-dichloro-3-hydroxy-1H,3H,5H-imidazolidino[2,1-b]quinazolin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  O   UNK     0       2.983  -0.902   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.924  -2.843   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       8.925  -0.533   0.000  0.00  0.00          Cl+0
HETATM    8  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0      11.592  -2.073   0.000  0.00  0.00          Cl+0
HETATM   10  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.258  -5.153   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       3.459  -4.859   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.014  -3.613   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    2   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₇Cl₂N₃O₂

Average Molecular Weight

272.087

Monoisotopic Molecular Weight

270.991531897

IUPAC Name

6,7-dichloro-3-hydroxy-1H,2H,3H,5H-imidazolidino[2,1-b]quinazolin-2-one

Traditional Name

6,7-dichloro-3-hydroxy-1H,3H,5H-imidazolidino[2,1-b]quinazolin-2-one

CAS Registry Number

Not Available

SMILES

OC1N2CC3=C(Cl)C(Cl)=CC=C3N=C2NC1=O

InChI Identifier

InChI=1S/C10H7Cl2N3O2/c11-5-1-2-6-4(7(5)12)3-15-9(17)8(16)14-10(15)13-6/h1-2,9,17H,3H2,(H,13,14,16)

InChI Key

KAXTUTDKZVOONF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinazolines

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Quinazoline
Aryl chloride
Aryl halide
Imidazolinone
Benzenoid
2-imidazoline
Guanidine
N-acylimine
Alkanolamine
Carboxylic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen 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 (HMDB: HMDB0060793)

Organ

Kidney (HMDB: HMDB0060793)
Liver (HMDB: HMDB0060793)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060793)

Cellular substructure

Cytoplasm (HMDB: HMDB0060793)

Source

Endogenous

Endogenous (HMDB: HMDB0060793)

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
Water Solubility	0.44 g/L	ALOGPS
logP	1.27	ALOGPS
logP	1.66	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.37	ChemAxon
pKa (Strongest Basic)	1.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.93 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	64.45 m³·mol⁻¹	ChemAxon
Polarizability	24.41 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+H]+	152.316	30932474
DeepCCS	[M-H]-	149.958	30932474
DeepCCS	[M-2H]-	183.381	30932474
DeepCCS	[M+Na]+	158.409	30932474
AllCCS	[M+H]+	155.2	32859911
AllCCS	[M+H-H2O]+	151.5	32859911
AllCCS	[M+NH4]+	158.6	32859911
AllCCS	[M+Na]+	159.6	32859911
AllCCS	[M-H]-	152.8	32859911
AllCCS	[M+Na-2H]-	152.4	32859911
AllCCS	[M+HCOO]-	152.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one	OC1N2CC3=C(Cl)C(Cl)=CC=C3N=C2NC1=O	3975.7	Standard polar	33892256
6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one	OC1N2CC3=C(Cl)C(Cl)=CC=C3N=C2NC1=O	2414.7	Standard non polar	33892256
6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one	OC1N2CC3=C(Cl)C(Cl)=CC=C3N=C2NC1=O	2599.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one,1TMS,isomer #1	C[Si](C)(C)OC1C(=O)NC2=NC3=CC=C(Cl)C(Cl)=C3CN21	2700.7	Semi standard non polar	33892256
6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one,1TMS,isomer #2	C[Si](C)(C)N1C(=O)C(O)N2CC3=C(C=CC(Cl)=C3Cl)N=C21	2550.6	Semi standard non polar	33892256
6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one,2TMS,isomer #1	C[Si](C)(C)OC1C(=O)N([Si](C)(C)C)C2=NC3=CC=C(Cl)C(Cl)=C3CN21	2507.7	Semi standard non polar	33892256
6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one,2TMS,isomer #1	C[Si](C)(C)OC1C(=O)N([Si](C)(C)C)C2=NC3=CC=C(Cl)C(Cl)=C3CN21	2409.7	Standard non polar	33892256
6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one,2TMS,isomer #1	C[Si](C)(C)OC1C(=O)N([Si](C)(C)C)C2=NC3=CC=C(Cl)C(Cl)=C3CN21	3557.9	Standard polar	33892256
6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(=O)NC2=NC3=CC=C(Cl)C(Cl)=C3CN21	2911.0	Semi standard non polar	33892256
6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)C(O)N2CC3=C(C=CC(Cl)=C3Cl)N=C21	2766.0	Semi standard non polar	33892256
6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(=O)N([Si](C)(C)C(C)(C)C)C2=NC3=CC=C(Cl)C(Cl)=C3CN21	2865.5	Semi standard non polar	33892256
6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(=O)N([Si](C)(C)C(C)(C)C)C2=NC3=CC=C(Cl)C(Cl)=C3CN21	2858.7	Standard non polar	33892256
6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(=O)N([Si](C)(C)C(C)(C)C)C2=NC3=CC=C(Cl)C(Cl)=C3CN21	3540.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0036-9240000000-1b013787489222fcce66	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9101000000-04d385462b06c5f79347	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one 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 - 6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one 10V, Positive-QTOF	splash10-00di-0090000000-a7fa230603950d0e5bf0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one 20V, Positive-QTOF	splash10-00di-0090000000-40c9b521f8308d598ad3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one 40V, Positive-QTOF	splash10-01ow-5890000000-9e8c566f8a9521c0527c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one 10V, Negative-QTOF	splash10-014i-0090000000-7d1999107b0d6faf4c7c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one 20V, Negative-QTOF	splash10-0006-9030000000-f8b36094f47b9e4faca4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one 40V, Negative-QTOF	splash10-0006-9110000000-f01e9fd2e648c5160fcb	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11579917

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

Not Available

Showing metabocard for 6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one (HMDB0060793)

MOL for HMDB0060793 (6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one)

3D MOL for HMDB0060793 (6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one)

3D SDF for HMDB0060793 (6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one)

3D-SDF for HMDB0060793 (6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one)

PDB for HMDB0060793 (6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one)

3D PDB for HMDB0060793 (6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one)

SMILES for HMDB0060793 (6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one)

INCHI for HMDB0060793 (6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one)

Structure for HMDB0060793 (6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one)

3D Structure for HMDB0060793 (6,7-Dichloro-3-hydroxy-1,5 dihydro-imidazo[2,1-b]quinazolin-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra