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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:56:30 UTC

Update Date

2021-09-26 23:06:43 UTC

HMDB ID

HMDB0253473

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Indolo[2,1-b]quinazoline-6,12-dione

Description

6H,12H-indolo[2,1-b]quinazoline-6,12-dione belongs to the class of organic compounds known as indoloquinazolines. These are polycyclic aromatic compounds containing an indole fused to a quinazoline. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Quinazoline is a heterocyclic compound consisting of two fused six-membered simple aromatic rings, a benzene ring and a pyrimidine ring. 6H,12H-indolo[2,1-b]quinazoline-6,12-dione 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 ). Indolo[2,1-b]quinazoline-6,12-dione is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Indolo[2,1-b]quinazoline-6,12-dione 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


  Mrv1533004171514092D          

 19 22  0  0  0  0            999 V2000
    2.8119    1.7485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745    0.9396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553    0.3944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997   -0.6780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9189   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1571    0.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754    1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990   -0.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037   -1.6385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920   -0.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706   -0.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069    0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369    1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  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
  2 11  1  0  0  0  0
  6 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  3 19  1  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253473

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1C2=NC3=CC=CC=C3C(=O)N2C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H8N2O2/c18-13-10-6-2-4-8-12(10)17-14(13)16-11-7-3-1-5-9(11)15(17)19/h1-8H

> <INCHI_KEY>
VQQVWGVXDIPORV-UHFFFAOYSA-N

> <FORMULA>
C15H8N2O2

> <MOLECULAR_WEIGHT>
248.241

> <EXACT_MASS>
248.058577506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
25.261525592272466

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6H,12H-indolo[2,1-b]quinazoline-6,12-dione

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
2.3956623936666666

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.94101239979379

> <JCHEM_POLAR_SURFACE_AREA>
49.74

> <JCHEM_REFRACTIVITY>
71.61820000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tryptanthrin

> <JCHEM_VEBER_RULE>
0

$$$$

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       5.249   3.264   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.552   1.754   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.397   0.736   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.700  -0.774   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       6.159  -1.266   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.315  -0.248   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.774  -0.740   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.930   0.278   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.627   1.788   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.167   2.280   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.012   1.262   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.358  -1.529   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.180  -3.059   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.225  -0.486   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.692  -0.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.200   0.626   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.442   2.026   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.976   2.170   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.867   0.914   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    2    6                                                  
CONECT   12    4   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    3   14                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

COMPND    HMDB0253473
HETATM    1  O1  UNL     1      -1.489  -2.205   2.454  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.359  -1.401   1.502  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.394  -0.841   0.658  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.785  -0.998   0.624  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.488  -0.302  -0.331  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.877   0.525  -1.234  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.513   0.671  -1.190  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.776  -0.010  -0.248  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.356   0.007  -0.041  1.00  0.00           N  
HETATM   10  C8  UNL     1      -0.110  -0.815   0.994  1.00  0.00           C  
HETATM   11  N2  UNL     1       1.158  -1.009   1.433  1.00  0.00           N  
HETATM   12  C9  UNL     1       2.153  -0.359   0.805  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.482  -0.518   1.212  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.511   0.143   0.578  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.267   0.987  -0.483  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.970   1.159  -0.899  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.920   0.488  -0.256  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.623   0.666  -0.680  1.00  0.00           C  
HETATM   19  O2  UNL     1       0.348   1.423  -1.640  1.00  0.00           O  
HETATM   20  H1  UNL     1      -4.246  -1.655   1.345  1.00  0.00           H  
HETATM   21  H2  UNL     1      -5.568  -0.437  -0.341  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.459   1.078  -1.996  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.035   1.325  -1.905  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.670  -1.190   2.055  1.00  0.00           H  
HETATM   25  H6  UNL     1       5.530  -0.021   0.941  1.00  0.00           H  
HETATM   26  H7  UNL     1       5.106   1.484  -0.948  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.715   1.807  -1.724  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4    4    8
CONECT    4    5   20
CONECT    5    6    6   21
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9
CONECT    9   10   18
CONECT   10   11   11
CONECT   11   12
CONECT   12   13   13   17
CONECT   13   14   24
CONECT   14   15   15   25
CONECT   15   16   26
CONECT   16   17   17   27
CONECT   17   18
CONECT   18   19   19
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Tryptanthrine	MeSH
6,12-Dihydro-6,12-dioxoindole(2,1-b)quinazoline	MeSH
Tryptanthrin	MeSH

Chemical Formula

C₁₅H₈N₂O₂

Average Molecular Weight

248.241

Monoisotopic Molecular Weight

248.058577506

IUPAC Name

6H,12H-indolo[2,1-b]quinazoline-6,12-dione

Traditional Name

tryptanthrin

CAS Registry Number

Not Available

SMILES

O=C1C2=NC3=CC=CC=C3C(=O)N2C2=CC=CC=C12

InChI Identifier

InChI=1S/C15H8N2O2/c18-13-10-6-2-4-8-12(10)17-14(13)16-11-7-3-1-5-9(11)15(17)19/h1-8H

InChI Key

VQQVWGVXDIPORV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoloquinazolines. These are polycyclic aromatic compounds containing an indole fused to a quinazoline. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Quinazoline is a heterocyclic compound consisting of two fused six-membered simple aromatic rings, a benzene ring and a pyrimidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Indoloquinazolines

Alternative Parents

Substituents

Indoloquinazoline
Indole
Indole or derivatives
Aryl ketone
Pyrimidone
Pyrimidine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Ketone
Lactam
Azacycle
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotetracyclic compound (CHEBI:9768 )
organonitrogen heterocyclic compound (CHEBI:9768 )
alkaloid antibiotic (CHEBI:9768 )
Quinazoline alkaloids (C10742 )

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	1.8	ALOGPS
logP	2.4	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.74 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.62 m³·mol⁻¹	ChemAxon
Polarizability	25.26 Å³	ChemAxon
Number of Rings	4	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]-	188.138	30932474
DeepCCS	[M+Na]+	163.518	30932474
AllCCS	[M+H]+	154.3	32859911
AllCCS	[M+H-H2O]+	150.4	32859911
AllCCS	[M+NH4]+	157.9	32859911
AllCCS	[M+Na]+	159.0	32859911
AllCCS	[M-H]-	157.9	32859911
AllCCS	[M+Na-2H]-	156.7	32859911
AllCCS	[M+HCOO]-	155.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Indolo[2,1-b]quinazoline-6,12-dione	O=C1C2=NC3=CC=CC=C3C(=O)N2C2=CC=CC=C12	3335.9	Standard polar	33892256
Indolo[2,1-b]quinazoline-6,12-dione	O=C1C2=NC3=CC=CC=C3C(=O)N2C2=CC=CC=C12	2367.6	Standard non polar	33892256
Indolo[2,1-b]quinazoline-6,12-dione	O=C1C2=NC3=CC=CC=C3C(=O)N2C2=CC=CC=C12	2557.0	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 - Indolo[2,1-b]quinazoline-6,12-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-006t-0090000000-e0b1af0c04d8954ccb97	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indolo[2,1-b]quinazoline-6,12-dione 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 - Indolo[2,1-b]quinazoline-6,12-dione 10V, Positive-QTOF	splash10-0002-0090000000-02816af0a0f47a8fd282	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indolo[2,1-b]quinazoline-6,12-dione 20V, Positive-QTOF	splash10-0002-0090000000-02816af0a0f47a8fd282	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indolo[2,1-b]quinazoline-6,12-dione 40V, Positive-QTOF	splash10-0002-0090000000-02816af0a0f47a8fd282	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indolo[2,1-b]quinazoline-6,12-dione 10V, Negative-QTOF	splash10-0002-0090000000-751003864ddf8d4279fd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indolo[2,1-b]quinazoline-6,12-dione 20V, Negative-QTOF	splash10-0002-0090000000-751003864ddf8d4279fd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indolo[2,1-b]quinazoline-6,12-dione 40V, Negative-QTOF	splash10-0002-0090000000-c5475e99e6d4332275f2	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

C00002200

Chemspider ID

Not Available

KEGG Compound ID

C10742

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73549

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 Indolo[2,1-b]quinazoline-6,12-dione (HMDB0253473)

MOL for HMDB0253473 (Indolo[2,1-b]quinazoline-6,12-dione)

3D MOL for HMDB0253473 (Indolo[2,1-b]quinazoline-6,12-dione)

3D SDF for HMDB0253473 (Indolo[2,1-b]quinazoline-6,12-dione)

3D-SDF for HMDB0253473 (Indolo[2,1-b]quinazoline-6,12-dione)

PDB for HMDB0253473 (Indolo[2,1-b]quinazoline-6,12-dione)

3D PDB for HMDB0253473 (Indolo[2,1-b]quinazoline-6,12-dione)

SMILES for HMDB0253473 (Indolo[2,1-b]quinazoline-6,12-dione)

INCHI for HMDB0253473 (Indolo[2,1-b]quinazoline-6,12-dione)

Structure for HMDB0253473 (Indolo[2,1-b]quinazoline-6,12-dione)

3D Structure for HMDB0253473 (Indolo[2,1-b]quinazoline-6,12-dione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra