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Showing metabocard for Cinnoline (HMDB0250265)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 07:14:56 UTC
Update Date2021-09-26 23:01:37 UTC
HMDB IDHMDB0250265
Secondary Accession NumbersNone
Metabolite Identification
Common NameCinnoline
DescriptionCinnoline, also known as 1,2-benzodiazine or benzopyridazine, belongs to the class of organic compounds known as cinnolines. These are organic aromatic compounds containing a benzene fused to a pyridazine ring. Based on a literature review a significant number of articles have been published on Cinnoline. This compound has been identified in human blood as reported by (PMID: 31557052 ). Cinnoline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cinnoline 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0250265 (Cinnoline)


  Mrv1652309112109152D          

 10 11  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  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
  4 10  1  0  0  0  0
M  END
Download

3D MOL for HMDB0250265 (Cinnoline)

HMDB0250265
     RDKit          3D
Cinnoline
 16 17  0  0  0  0  0  0  0  0999 V2000
   -2.0745   -0.6172   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2174    0.7401    0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0501    1.5000    0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2044    0.9290    0.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3414    1.6318    0.2149 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5306    1.0910    0.1431 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7043   -0.2197   -0.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882   -1.0097   -0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432   -0.4335   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8263   -1.1900   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9724   -1.2057   -0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1846    1.2209    0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1079    2.5506    0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7035   -0.6401   -0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6998   -2.0880   -0.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823   -2.2595   -0.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  1  1  0
  9  4  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  7 14  1  0
  8 15  1  0
 10 16  1  0
M  END
Download

3D SDF for HMDB0250265 (Cinnoline)


  Mrv1652309112109152D          

 10 11  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  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
  4 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250265

> <DATABASE_NAME>
hmdb

> <SMILES>
C1=CC=C2N=NC=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H6N2/c1-2-4-8-7(3-1)5-6-9-10-8/h1-6H

> <INCHI_KEY>
WCZVZNOTHYJIEI-UHFFFAOYSA-N

> <FORMULA>
C8H6N2

> <MOLECULAR_WEIGHT>
130.15

> <EXACT_MASS>
130.053098201

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
13.214240352514915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
cinnoline

> <ALOGPS_LOGP>
0.95

> <JCHEM_LOGP>
1.1511305196666668

> <ALOGPS_LOGS>
-1.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.0682267163677057

> <JCHEM_POLAR_SURFACE_AREA>
25.78

> <JCHEM_REFRACTIVITY>
39.8426

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cinnoline

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0250265 (Cinnoline)

HMDB0250265
     RDKit          3D
Cinnoline
 16 17  0  0  0  0  0  0  0  0999 V2000
   -2.0745   -0.6172   -0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2174    0.7401    0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0501    1.5000    0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2044    0.9290    0.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3414    1.6318    0.2149 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5306    1.0910    0.1431 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7043   -0.2197   -0.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882   -1.0097   -0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432   -0.4335   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8263   -1.1900   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9724   -1.2057   -0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1846    1.2209    0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1079    2.5506    0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7035   -0.6401   -0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6998   -2.0880   -0.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823   -2.2595   -0.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  1  1  0
  9  4  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  7 14  1  0
  8 15  1  0
 10 16  1  0
M  END
Download

PDB for HMDB0250265 (Cinnoline)

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END
Download

3D PDB for HMDB0250265 (Cinnoline)

COMPND    HMDB0250265
HETATM    1  C1  UNL     1      -2.074  -0.617  -0.081  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.217   0.740   0.098  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.050   1.500   0.198  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.204   0.929   0.123  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.341   1.632   0.215  1.00  0.00           N  
HETATM    6  N2  UNL     1       2.531   1.091   0.143  1.00  0.00           N  
HETATM    7  C5  UNL     1       2.704  -0.220  -0.030  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.588  -1.010  -0.134  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.343  -0.433  -0.057  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.826  -1.190  -0.157  1.00  0.00           C  
HETATM   11  H1  UNL     1      -2.972  -1.206  -0.158  1.00  0.00           H  
HETATM   12  H2  UNL     1      -3.185   1.221   0.162  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.108   2.551   0.337  1.00  0.00           H  
HETATM   14  H4  UNL     1       3.704  -0.640  -0.086  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.700  -2.088  -0.276  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.682  -2.260  -0.298  1.00  0.00           H  
CONECT    1    2    2   10   11
CONECT    2    3   12
CONECT    3    4    4   13
CONECT    4    5    9
CONECT    5    6    6
CONECT    6    7
CONECT    7    8    8   14
CONECT    8    9   15
CONECT    9   10   10
CONECT   10   16
END
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SMILES for HMDB0250265 (Cinnoline)

C1=CC=C2N=NC=CC2=C1
Download

INCHI for HMDB0250265 (Cinnoline)

InChI=1S/C8H6N2/c1-2-4-8-7(3-1)5-6-9-10-8/h1-6H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1,2-BenzodiazineChEBI
1,2-DiazanaphthaleneChEBI
alpha-PhenodiazineChEBI
Benzo[c]pyridazineChEBI
BenzopyridazineChEBI
a-PhenodiazineGenerator
Α-phenodiazineGenerator
HexahydrocinnolineHMDB
Chemical FormulaC8H6N2
Average Molecular Weight130.15
Monoisotopic Molecular Weight130.053098201
IUPAC Namecinnoline
Traditional Namecinnoline
CAS Registry NumberNot Available
SMILES
C1=CC=C2N=NC=CC2=C1
InChI Identifier
InChI=1S/C8H6N2/c1-2-4-8-7(3-1)5-6-9-10-8/h1-6H
InChI KeyWCZVZNOTHYJIEI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnolines. These are organic aromatic compounds containing a benzene fused to a pyridazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentCinnolines
Alternative Parents
Substituents
  • Cinnoline
  • Benzenoid
  • Pyridazine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0.95ALOGPS
logP1.15ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)3.07ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.84 m³·mol⁻¹ChemAxon
Polarizability13.21 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+126.78730932474
DeepCCS[M-H]-123.66330932474
DeepCCS[M-2H]-160.58530932474
DeepCCS[M+Na]+135.82430932474
AllCCS[M+H]+125.132859911
AllCCS[M+H-H2O]+120.132859911
AllCCS[M+NH4]+129.832859911
AllCCS[M+Na]+131.132859911
AllCCS[M-H]-123.332859911
AllCCS[M+Na-2H]-124.432859911
AllCCS[M+HCOO]-125.632859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 20229.8779 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.02 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1223.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid380.1 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid134.6 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid244.7 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid189.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid333.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid357.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)107.3 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid750.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid256.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid860.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid252.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid317.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate472.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA265.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water84.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CinnolineC1=CC=C2N=NC=CC2=C12103.7Standard polar33892256
CinnolineC1=CC=C2N=NC=CC2=C11308.8Standard non polar33892256
CinnolineC1=CC=C2N=NC=CC2=C11347.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cinnoline GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-0900000000-4e74f9845b3dd2d907682021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinnoline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnoline 10V, Positive-QTOFsplash10-001i-0900000000-fb0dcf80a365c79dd7542021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnoline 20V, Positive-QTOFsplash10-0f89-0900000000-7e8c974d4534dadb5dcd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnoline 40V, Positive-QTOFsplash10-0fb9-9500000000-8c1239e4681d82f3b2d72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnoline 10V, Negative-QTOFsplash10-004i-0900000000-92ad1adb0c25799beef62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnoline 20V, Negative-QTOFsplash10-004i-0900000000-92ad1adb0c25799beef62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnoline 40V, Negative-QTOFsplash10-004i-0900000000-4c8c4193ccca39e2454e2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8853
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCinnoline
METLIN IDNot Available
PubChem Compound9208
PDB IDNot Available
ChEBI ID36617
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]