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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:31:24 UTC

Update Date

2021-09-26 23:11:42 UTC

HMDB ID

HMDB0256199

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol

Description

1H,2H,3H,9H-pyrrolo[2,1-b]quinazolin-3-ol 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 1H,2H,3H,9H-pyrrolo[2,1-b]quinazolin-3-ol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-3-ol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol 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


  Mrv1533004171500072D          

 14 16  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
    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  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  2 14  1  0  0  0  0
  5 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256199

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CCN2CC3=CC=CC=C3N=C12

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O/c14-10-5-6-13-7-8-3-1-2-4-9(8)12-11(10)13/h1-4,10,14H,5-7H2

> <INCHI_KEY>
YIICVSCAKJMMDJ-UHFFFAOYSA-N

> <FORMULA>
C11H12N2O

> <MOLECULAR_WEIGHT>
188.23

> <EXACT_MASS>
188.094963014

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.46243186138894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.74

> <JCHEM_LOGP>
0.6625927100000002

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.752518371435212

> <JCHEM_PKA_STRONGEST_BASIC>
8.221058270097284

> <JCHEM_POLAR_SURFACE_AREA>
35.83

> <JCHEM_REFRACTIVITY>
56.30140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.05e+00 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

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       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  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+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
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    2    5                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END

COMPND    HMDB0256199
HETATM    1  O1  UNL     1      -2.887   0.730   1.591  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.545   0.894   0.258  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.157  -0.236  -0.559  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.248  -1.411  -0.336  1.00  0.00           C  
HETATM    5  N1  UNL     1      -0.923  -0.747  -0.254  1.00  0.00           N  
HETATM    6  C4  UNL     1       0.390  -1.310  -0.527  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.474  -0.385  -0.184  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.796  -0.825  -0.314  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.873  -0.027  -0.036  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.643   1.264   0.391  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.352   1.711   0.524  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.258   0.903   0.242  1.00  0.00           C  
HETATM   13  N2  UNL     1      -0.064   1.370   0.403  1.00  0.00           N  
HETATM   14  C11 UNL     1      -1.060   0.595   0.155  1.00  0.00           C  
HETATM   15  H1  UNL     1      -3.358   1.533   1.933  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.783   1.888  -0.135  1.00  0.00           H  
HETATM   17  H3  UNL     1      -4.189  -0.420  -0.172  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.246   0.022  -1.630  1.00  0.00           H  
HETATM   19  H5  UNL     1      -2.482  -1.926   0.609  1.00  0.00           H  
HETATM   20  H6  UNL     1      -2.219  -2.107  -1.198  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.459  -1.683  -1.577  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.452  -2.222   0.139  1.00  0.00           H  
HETATM   23  H9  UNL     1       2.986  -1.842  -0.650  1.00  0.00           H  
HETATM   24  H10 UNL     1       4.906  -0.403  -0.148  1.00  0.00           H  
HETATM   25  H11 UNL     1       4.463   1.908   0.615  1.00  0.00           H  
HETATM   26  H12 UNL     1       2.110   2.729   0.859  1.00  0.00           H  
CONECT    1    2   15
CONECT    2    3   14   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   14
CONECT    6    7   21   22
CONECT    7    8    8   12
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   13
CONECT   13   14   14
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Vasicine monohydrochloride, (R)-isomer	MeSH
Vasicine, (+-)-isomer	MeSH
Peganine hydrochloride dihydrate	MeSH
Vasicine	MeSH
Vasicine hydrochloride, (R)-isomer	MeSH
Peganine	MeSH

Chemical Formula

C₁₁H₁₂N₂O

Average Molecular Weight

188.23

Monoisotopic Molecular Weight

188.094963014

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC1CCN2CC3=CC=CC=C3N=C12

InChI Identifier

InChI=1S/C11H12N2O/c14-10-5-6-13-7-8-3-1-2-4-9(8)12-11(10)13/h1-4,10,14H,5-7H2

InChI Key

YIICVSCAKJMMDJ-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
N-alkylpyrrolidine
Benzenoid
Imidolactam
Pyrrolidine
Secondary alcohol
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Amidine
Carboxylic acid amidine
Alcohol
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen 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)

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	0.74	ALOGPS
logP	0.66	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	13.75	ChemAxon
pKa (Strongest Basic)	8.22	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	56.3 m³·mol⁻¹	ChemAxon
Polarizability	20.46 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	177.631	30932474
DeepCCS	[M+Na]+	153.169	30932474
AllCCS	[M+H]+	142.7	32859911
AllCCS	[M+H-H2O]+	138.5	32859911
AllCCS	[M+NH4]+	146.7	32859911
AllCCS	[M+Na]+	147.8	32859911
AllCCS	[M-H]-	144.4	32859911
AllCCS	[M+Na-2H]-	144.5	32859911
AllCCS	[M+HCOO]-	144.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol	OC1CCN2CC3=CC=CC=C3N=C12	2770.6	Standard polar	33892256
1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol	OC1CCN2CC3=CC=CC=C3N=C12	1886.2	Standard non polar	33892256
1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol	OC1CCN2CC3=CC=CC=C3N=C12	1968.5	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 - 1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fb9-4900000000-a64e004ceb2759754ec7	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol 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 - 1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol 6V, Positive-QTOF	splash10-000i-0900000000-271508f8ace71319f388	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)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	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

65485

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

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 1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol (HMDB0256199)

MOL for HMDB0256199 (1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol)

3D MOL for HMDB0256199 (1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol)

3D SDF for HMDB0256199 (1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol)

3D-SDF for HMDB0256199 (1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol)

PDB for HMDB0256199 (1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol)

3D PDB for HMDB0256199 (1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol)

SMILES for HMDB0256199 (1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol)

INCHI for HMDB0256199 (1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol)

Structure for HMDB0256199 (1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol)

3D Structure for HMDB0256199 (1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra