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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:32:11 UTC

Update Date

2021-09-26 22:59:39 UTC

HMDB ID

HMDB0249051

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Benzoyleneurea

Description

quinazoline-2,4-diol 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. quinazoline-2,4-diol is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Benzoyleneurea is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Benzoyleneurea 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

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11    2                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Quinazoline-24-diol	ChEMBL
2,4-Quinazolinedione	MeSH
2,4(1H,3H)-Quinazolinedione	MeSH
2,4(1H,3H)-Quinazolinedione, 2-(11C-labeled)	MeSH

Chemical Formula

C₈H₆N₂O₂

Average Molecular Weight

162.148

Monoisotopic Molecular Weight

162.042927441

IUPAC Name

1,2,3,4-tetrahydroquinazoline-2,4-dione

Traditional Name

1,3-dihydroquinazoline-2,4-dione

CAS Registry Number

Not Available

SMILES

O=C1NC(=O)C2=CC=CC=C2N1

InChI Identifier

InChI=1S/C8H6N2O2/c11-7-5-3-1-2-4-6(5)9-8(12)10-7/h1-4H,(H2,9,10,11,12)

InChI Key

SDQJTWBNWQABLE-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

Quinazoline
Pyrimidone
Pyrimidine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Lactam
Urea
Azacycle
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
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 (PMID: 31557052)

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	0.42	ALOGPS
logP	1.4	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.66	ChemAxon
pKa (Strongest Basic)	-8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.2 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	43.78 m³·mol⁻¹	ChemAxon
Polarizability	15.03 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
DeepCCS	[M+H]+	126.78	30932474
DeepCCS	[M-H]-	122.95	30932474
DeepCCS	[M-2H]-	160.237	30932474
DeepCCS	[M+Na]+	135.776	30932474
AllCCS	[M+H]+	136.2	32859911
AllCCS	[M+H-H2O]+	131.8	32859911
AllCCS	[M+NH4]+	140.3	32859911
AllCCS	[M+Na]+	141.4	32859911
AllCCS	[M-H]-	130.7	32859911
AllCCS	[M+Na-2H]-	131.5	32859911
AllCCS	[M+HCOO]-	132.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.1713 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.86 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	762.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	338.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	104.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	211.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	73.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	285.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	310.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	179.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	631.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	282.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	794.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	229.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	260.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	512.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	269.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	139.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzoyleneurea	O=C1NC(=O)C2=CC=CC=C2N1	2792.7	Standard polar	33892256
Benzoyleneurea	O=C1NC(=O)C2=CC=CC=C2N1	1958.2	Standard non polar	33892256
Benzoyleneurea	O=C1NC(=O)C2=CC=CC=C2N1	1939.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Benzoyleneurea,1TMS,isomer #1	C[Si](C)(C)N1C(=O)[NH]C2=CC=CC=C2C1=O	1979.9	Semi standard non polar	33892256
Benzoyleneurea,1TMS,isomer #1	C[Si](C)(C)N1C(=O)[NH]C2=CC=CC=C2C1=O	1895.5	Standard non polar	33892256
Benzoyleneurea,1TMS,isomer #1	C[Si](C)(C)N1C(=O)[NH]C2=CC=CC=C2C1=O	2352.4	Standard polar	33892256
Benzoyleneurea,1TMS,isomer #2	C[Si](C)(C)N1C(=O)[NH]C(=O)C2=CC=CC=C21	1943.9	Semi standard non polar	33892256
Benzoyleneurea,1TMS,isomer #2	C[Si](C)(C)N1C(=O)[NH]C(=O)C2=CC=CC=C21	1937.7	Standard non polar	33892256
Benzoyleneurea,1TMS,isomer #2	C[Si](C)(C)N1C(=O)[NH]C(=O)C2=CC=CC=C21	2285.7	Standard polar	33892256
Benzoyleneurea,2TMS,isomer #1	C[Si](C)(C)N1C(=O)C2=CC=CC=C2N([Si](C)(C)C)C1=O	2132.4	Semi standard non polar	33892256
Benzoyleneurea,2TMS,isomer #1	C[Si](C)(C)N1C(=O)C2=CC=CC=C2N([Si](C)(C)C)C1=O	2004.1	Standard non polar	33892256
Benzoyleneurea,2TMS,isomer #1	C[Si](C)(C)N1C(=O)C2=CC=CC=C2N([Si](C)(C)C)C1=O	2081.4	Standard polar	33892256
Benzoyleneurea,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=CC=CC=C2C1=O	2104.8	Semi standard non polar	33892256
Benzoyleneurea,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=CC=CC=C2C1=O	2093.7	Standard non polar	33892256
Benzoyleneurea,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=CC=CC=C2C1=O	2426.5	Standard polar	33892256
Benzoyleneurea,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)[NH]C(=O)C2=CC=CC=C21	2119.7	Semi standard non polar	33892256
Benzoyleneurea,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)[NH]C(=O)C2=CC=CC=C21	2136.8	Standard non polar	33892256
Benzoyleneurea,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)[NH]C(=O)C2=CC=CC=C21	2376.6	Standard polar	33892256
Benzoyleneurea,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C2=CC=CC=C2N([Si](C)(C)C(C)(C)C)C1=O	2421.7	Semi standard non polar	33892256
Benzoyleneurea,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C2=CC=CC=C2N([Si](C)(C)C(C)(C)C)C1=O	2391.2	Standard non polar	33892256
Benzoyleneurea,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C2=CC=CC=C2N([Si](C)(C)C(C)(C)C)C1=O	2316.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoyleneurea GC-MS (Non-derivatized) - 70eV, Positive	splash10-03xr-1900000000-b7e76a99867acf5d819f	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoyleneurea 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 - Benzoyleneurea 10V, Positive-QTOF	splash10-03di-0900000000-6f6bcbba114aec782dc0	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyleneurea 20V, Positive-QTOF	splash10-03di-0900000000-0024e9142cf20da392a4	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyleneurea 40V, Positive-QTOF	splash10-022a-3900000000-3c2df9bcf23d21fdb19f	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyleneurea 10V, Negative-QTOF	splash10-03di-0900000000-e91ef93b56ad2809bc96	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyleneurea 20V, Negative-QTOF	splash10-03di-2900000000-a0412d376a65405c3ef7	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyleneurea 40V, Negative-QTOF	splash10-00kf-7900000000-b1f493662f689324ab77	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyleneurea 10V, Negative-QTOF	splash10-03di-0900000000-245b05009ee1c93744d6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyleneurea 20V, Negative-QTOF	splash10-03di-2900000000-978535e8c6c5d2ae75d2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyleneurea 40V, Negative-QTOF	splash10-0006-9100000000-0cbcc383091ff2cde826	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyleneurea 10V, Positive-QTOF	splash10-03di-0900000000-3fd3f930d26ee957274d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyleneurea 20V, Positive-QTOF	splash10-00di-0900000000-901b9dab611625c03bf8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoyleneurea 40V, Positive-QTOF	splash10-0g4l-9500000000-7b01a887219fad1d990c	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

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

64048

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 Benzoyleneurea (HMDB0249051)

MOL for HMDB0249051 (Benzoyleneurea)

3D MOL for HMDB0249051 (Benzoyleneurea)

3D SDF for HMDB0249051 (Benzoyleneurea)

3D-SDF for HMDB0249051 (Benzoyleneurea)

PDB for HMDB0249051 (Benzoyleneurea)

3D PDB for HMDB0249051 (Benzoyleneurea)

SMILES for HMDB0249051 (Benzoyleneurea)

INCHI for HMDB0249051 (Benzoyleneurea)

Structure for HMDB0249051 (Benzoyleneurea)

3D Structure for HMDB0249051 (Benzoyleneurea)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra