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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:38:26 UTC

Update Date

2022-11-23 22:29:21 UTC

HMDB ID

HMDB0259770

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Vasicinone

Description

3-hydroxy-1H,2H,3H,9H-pyrrolo[2,1-b]quinazolin-9-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. Based on a literature review very few articles have been published on 3-hydroxy-1H,2H,3H,9H-pyrrolo[2,1-b]quinazolin-9-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). Vasicinone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Vasicinone 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

  Mrv1533004161519342D          

 15 17  0  0  0  0            999 V2000
    1.5983   -3.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   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
    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
    3.3523   -0.2854    0.0000 O   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
    5.4957   -1.5229    0.0000 C   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  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  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  2 15  1  0  0  0  0
  5 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259770

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CCN2C1=NC1=CC=CC=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H10N2O2/c14-9-5-6-13-10(9)12-8-4-2-1-3-7(8)11(13)15/h1-4,9,14H,5-6H2

> <INCHI_KEY>
SDIVYZXRQHWCKF-UHFFFAOYSA-N

> <FORMULA>
C11H10N2O2

> <MOLECULAR_WEIGHT>
202.213

> <EXACT_MASS>
202.07422757

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
20.5872671590348

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-1H,2H,3H,9H-pyrrolo[2,1-b]quinazolin-9-one

> <ALOGPS_LOGP>
0.16

> <JCHEM_LOGP>
0.2802596043333333

> <ALOGPS_LOGS>
-1.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.698010015330905

> <JCHEM_PKA_STRONGEST_BASIC>
2.790299477977619

> <JCHEM_POLAR_SURFACE_AREA>
52.9

> <JCHEM_REFRACTIVITY>
56.63050000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-1H,2H,3H-pyrrolo[2,1-b]quinazolin-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0       2.983  -6.323   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       4.924  -2.843   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       6.258  -5.153   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14    2    5                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₁H₁₀N₂O₂

Average Molecular Weight

202.213

Monoisotopic Molecular Weight

202.07422757

IUPAC Name

3-hydroxy-1H,2H,3H,9H-pyrrolo[2,1-b]quinazolin-9-one

Traditional Name

3-hydroxy-1H,2H,3H-pyrrolo[2,1-b]quinazolin-9-one

CAS Registry Number

Not Available

SMILES

OC1CCN2C1=NC1=CC=CC=C1C2=O

InChI Identifier

InChI=1S/C11H10N2O2/c14-9-5-6-13-10(9)12-8-4-2-1-3-7(8)11(13)15/h1-4,9,14H,5-6H2

InChI Key

SDIVYZXRQHWCKF-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
Lactam
Secondary alcohol
Azacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen 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	0.16	ALOGPS
logP	0.28	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	13.7	ChemAxon
pKa (Strongest Basic)	2.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.9 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	56.63 m³·mol⁻¹	ChemAxon
Polarizability	20.59 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
AllCCS	[M+H]+	144.527	32859911
AllCCS	[M+H-H2O]+	140.332	32859911
AllCCS	[M+Na]+	149.559	32859911
AllCCS	[M+NH4]+	148.433	32859911
AllCCS	[M-H]-	146.056	32859911
AllCCS	[M+Na-2H]-	145.877	32859911
AllCCS	[M+HCOO]-	145.77	32859911
DeepCCS	[M+H]+	137.314	30932474
DeepCCS	[M-H]-	134.673	30932474
DeepCCS	[M-2H]-	170.741	30932474
DeepCCS	[M+Na]+	146.279	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
VASICINONE	OC1CCN2C1=NC1=CC=CC=C1C2=O	2866.2	Standard polar	33892256
VASICINONE	OC1CCN2C1=NC1=CC=CC=C1C2=O	2090.2	Standard non polar	33892256
VASICINONE	OC1CCN2C1=NC1=CC=CC=C1C2=O	2019.2	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 - Vasicinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0600-2900000000-f3ccfdc6a39ca808d422	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vasicinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vasicinone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vasicinone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vasicinone 6V, Positive-QTOF	splash10-0udi-0190000000-08cf84e49eb4fb8a6cc5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vasicinone 6V, Positive-QTOF	splash10-001i-1900000000-e2c31042fbc84b2148c2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vasicinone 6V, Positive-QTOF	splash10-0udr-0970000000-46f91581a08cf8a6f8cd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vasicinone 6V, Positive-QTOF	splash10-0019-1900000000-4079f45aae10e1d7e507	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vasicinone 6V, Positive-QTOF	splash10-0f79-0970000000-fe6f60687aa16b93c91e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vasicinone 6V, Positive-QTOF	splash10-0f79-0970000000-e34e5bb637adbe7a7319	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vasicinone 6V, Positive-QTOF	splash10-0udi-0190000000-719a1274f1ebfb96a516	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vasicinone 6V, Positive-QTOF	splash10-0f89-2900000000-babd15784f69d1d5ec92	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vasicinone 10V, Positive-QTOF	splash10-0udr-0790000000-2756bc677632f96b6f3a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vasicinone 6V, Positive-QTOF	splash10-0f89-2900000000-c2b4dbdfb07750c92b16	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vasicinone 20V, Positive-QTOF	splash10-000i-0900000000-c5c7527e136e0a5d59ac	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vasicinone 6V, Positive-QTOF	splash10-0019-0900000000-0b8147715dc4d55add13	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vasicinone 40V, Positive-QTOF	splash10-0f89-0900000000-b059b24f0690494ad389	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vasicinone 6V, Positive-QTOF	splash10-0019-1900000000-a7e03d8ec9143e66d671	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vasicinone 6V, Positive-QTOF	splash10-0udi-0190000000-d2e8299bc7f857d60289	2021-09-20	HMDB team, MONA	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	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

9825

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10242

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 Vasicinone (HMDB0259770)

MOL for HMDB0259770 (Vasicinone)

3D MOL for HMDB0259770 (Vasicinone)

3D SDF for HMDB0259770 (Vasicinone)

3D-SDF for HMDB0259770 (Vasicinone)

PDB for HMDB0259770 (Vasicinone)

3D PDB for HMDB0259770 (Vasicinone)

SMILES for HMDB0259770 (Vasicinone)

INCHI for HMDB0259770 (Vasicinone)

Structure for HMDB0259770 (Vasicinone)

3D Structure for HMDB0259770 (Vasicinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra