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Showing metabocard for Azulene (HMDB0248822)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 02:18:20 UTC
Update Date2021-09-26 22:59:19 UTC
HMDB IDHMDB0248822
Secondary Accession NumbersNone
Metabolite Identification
Common NameAzulene
DescriptionAzulene, also known as azulekeep, belongs to the class of organic compounds known as azulenes. These are polycyclic aromatic compounds containing the azulene skeleton, which consists of the cyclopentadiene ring fused to a cycloheptadiene ring. Azulene has been detected, but not quantified in, several different foods, such as german camomiles (Matricaria recutita), roman camomiles (Chamaemelum nobile), anises (Pimpinella anisum), wild carrots (Daucus carota), and turmerics (Curcuma longa). This could make azulene a potential biomarker for the consumption of these foods. Azulene is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Azulene. This compound has been identified in human blood as reported by (PMID: 31557052 ). Azulene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Azulene 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 HMDB0248822 (Azulene)


  Mrv0541 02241204302D          

 10 11  0  0  0  0            999 V2000
    0.4717   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -0.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -0.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -0.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -1.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -1.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -1.6436    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
  1 10  1  0  0  0  0
M  END
Download

3D MOL for HMDB0248822 (Azulene)

HMDB0248822
     RDKit          3D
Azulene
 18 19  0  0  0  0  0  0  0  0999 V2000
   -2.3959    0.1545   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7654    1.3626    0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4288    1.5616    0.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6225    0.6789    0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9685    0.9965    0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112   -0.1486    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8912   -1.2271   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5853   -0.7501   -0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5536   -1.4937   -0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8827   -1.1290   -0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4436    0.1945   -0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4341    2.2152    0.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1749    2.5429    0.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2992    2.0050    0.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7905   -0.2228    0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1850   -2.2553   -0.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3872   -2.5303   -0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5871   -1.9547   -0.0330 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
  8  4  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
 10 18  1  0
M  END
Download

3D SDF for HMDB0248822 (Azulene)


  Mrv0541 02241204302D          

 10 11  0  0  0  0            999 V2000
    0.4717   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -0.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -0.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -0.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -1.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -1.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -1.6436    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
  1 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248822

> <DATABASE_NAME>
hmdb

> <SMILES>
C1=CC2=CC=CC=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H

> <INCHI_KEY>
CUFNKYGDVFVPHO-UHFFFAOYSA-N

> <FORMULA>
C10H8

> <MOLECULAR_WEIGHT>
128.1705

> <EXACT_MASS>
128.062600256

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
14.698152313886654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
azulene

> <ALOGPS_LOGP>
3.51

> <JCHEM_LOGP>
2.9627225726666664

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
42.5082

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
azulene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0248822 (Azulene)

HMDB0248822
     RDKit          3D
Azulene
 18 19  0  0  0  0  0  0  0  0999 V2000
   -2.3959    0.1545   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7654    1.3626    0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4288    1.5616    0.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6225    0.6789    0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9685    0.9965    0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112   -0.1486    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8912   -1.2271   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5853   -0.7501   -0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5536   -1.4937   -0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8827   -1.1290   -0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4436    0.1945   -0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4341    2.2152    0.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1749    2.5429    0.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2992    2.0050    0.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7905   -0.2228    0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1850   -2.2553   -0.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3872   -2.5303   -0.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5871   -1.9547   -0.0330 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
  8  4  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
 10 18  1  0
M  END
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PDB for HMDB0248822 (Azulene)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.881  -1.822   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.786  -0.576   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.250  -1.052   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.454  -0.092   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.956  -0.435   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.624  -1.822   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.956  -3.210   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.454  -3.552   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.250  -2.592   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.786  -3.068   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9    1                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END
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3D PDB for HMDB0248822 (Azulene)

COMPND    HMDB0248822
HETATM    1  C1  UNL     1      -2.396   0.154  -0.201  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.765   1.363   0.062  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.429   1.562   0.332  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.623   0.679   0.189  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.969   0.996   0.298  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.711  -0.149   0.092  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.891  -1.227  -0.153  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.585  -0.750  -0.101  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.554  -1.494  -0.289  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.883  -1.129  -0.168  1.00  0.00           C  
HETATM   11  H1  UNL     1      -3.444   0.194  -0.475  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.434   2.215   0.042  1.00  0.00           H  
HETATM   13  H3  UNL     1      -0.175   2.543   0.707  1.00  0.00           H  
HETATM   14  H4  UNL     1       2.299   2.005   0.513  1.00  0.00           H  
HETATM   15  H5  UNL     1       3.791  -0.223   0.113  1.00  0.00           H  
HETATM   16  H6  UNL     1       2.185  -2.255  -0.351  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.387  -2.530  -0.578  1.00  0.00           H  
HETATM   18  H8  UNL     1      -2.587  -1.955  -0.033  1.00  0.00           H  
CONECT    1    2    2   10   11
CONECT    2    3   12
CONECT    3    4    4   13
CONECT    4    5    8
CONECT    5    6    6   14
CONECT    6    7   15
CONECT    7    8    8   16
CONECT    8    9
CONECT    9   10   10   17
CONECT   10   18
END
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SMILES for HMDB0248822 (Azulene)

C1=CC2=CC=CC=CC2=C1
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INCHI for HMDB0248822 (Azulene)

InChI=1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
AzulenChEBI
CyclopentacyclohepteneChEBI
AzulekeepHMDB
Chemical FormulaC10H8
Average Molecular Weight128.1705
Monoisotopic Molecular Weight128.062600256
IUPAC Nameazulene
Traditional Nameazulene
CAS Registry NumberNot Available
SMILES
C1=CC2=CC=CC=CC2=C1
InChI Identifier
InChI=1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H
InChI KeyCUFNKYGDVFVPHO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as azulenes. These are polycyclic aromatic compounds containing the azulene skeleton, which consists of the cyclopentadiene ring fused to a cycloheptadiene ring.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassUnsaturated hydrocarbons
Sub ClassOlefins
Direct ParentAzulenes
Alternative Parents
Substituents
  • Azulene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial applicationBiological role
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
logP3.51ALOGPS
logP2.96ChemAxon
logS-2.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.51 m³·mol⁻¹ChemAxon
Polarizability14.7 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]+128.49530932474
DeepCCS[M-H]-125.45630932474
DeepCCS[M-2H]-162.3430932474
DeepCCS[M+Na]+137.5730932474
AllCCS[M+H]+123.932859911
AllCCS[M+H-H2O]+118.932859911
AllCCS[M+NH4]+128.632859911
AllCCS[M+Na]+129.932859911
AllCCS[M-H]-122.332859911
AllCCS[M+Na-2H]-123.332859911
AllCCS[M+HCOO]-124.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AzuleneC1=CC2=CC=CC=CC2=C11751.7Standard polar33892256
AzuleneC1=CC2=CC=CC=CC2=C11274.6Standard non polar33892256
AzuleneC1=CC2=CC=CC=CC2=C11319.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Azulene GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0900000000-9100e2e177a5220488b82021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Azulene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-2900000000-ddfe7244d5f01ca469982014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azulene 10V, Positive-QTOFsplash10-004i-0900000000-c58668897462a120be2c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azulene 20V, Positive-QTOFsplash10-004i-0900000000-5a9b05b0e3abe8a17d1d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azulene 40V, Positive-QTOFsplash10-004i-1900000000-9435ad04abd5c7a3b5a62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azulene 10V, Negative-QTOFsplash10-004i-0900000000-878dba5e57117c17431d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azulene 20V, Negative-QTOFsplash10-004i-0900000000-c732623515fe642c30af2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azulene 40V, Negative-QTOFsplash10-004i-1900000000-79c79d6e40451aba8b2d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azulene 10V, Positive-QTOFsplash10-004i-0900000000-71e8922109bea9aa624a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azulene 20V, Positive-QTOFsplash10-004i-1900000000-18bcf87334724dba4c792021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azulene 40V, Positive-QTOFsplash10-03fr-9400000000-bfa403c802210a24e88e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azulene 10V, Negative-QTOFsplash10-004i-0900000000-ec6816397577a7beb93f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azulene 20V, Negative-QTOFsplash10-004i-0900000000-ec6816397577a7beb93f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azulene 40V, Negative-QTOFsplash10-004i-0900000000-2e84393d7d2cb0f2230f2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 IDFDB004830
KNApSAcK IDC00042269
Chemspider ID8876
KEGG Compound IDC13392
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAzulene
METLIN IDNot Available
PubChem Compound9231
PDB IDNot Available
ChEBI ID31249
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1220911
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 ]