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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:14:17 UTC

Update Date

2021-09-26 23:04:52 UTC

HMDB ID

HMDB0252354

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Fluoranthene

Description

Fluoranthene, also known as benzo[JK]fluorene, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Fluoranthene is possibly neutral. Fluoranthene is a potentially toxic compound. Fluoranthene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. PAHs are are formed during the incomplete burning of organic substances, such as fossil fuels. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. These enzymes metabolize PAH's into their toxic intermediates. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. They may also cause reproductive effects and depress the immune system. This compound has been identified in human blood as reported by (PMID: 31557052 ). Fluoranthene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Fluoranthene 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


  Mrv1652304272019052D          

 16 19  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5457    2.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0609    0.1715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2994    2.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0609    0.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8783    2.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3465   -0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3856    1.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9645    1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6320    0.1715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182    0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  5  2  0  0  0  0
  3  9  1  0  0  0  0
  4  6  2  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  2  0  0  0  0
  8 13  2  0  0  0  0
  9 14  2  0  0  0  0
 10 15  2  0  0  0  0
 11 16  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252354

> <DATABASE_NAME>
hmdb

> <SMILES>
C1=CC=C2C(=C1)C1=CC=CC3=C1C2=CC=C3

> <INCHI_IDENTIFIER>
InChI=1S/C16H10/c1-2-8-13-12(7-1)14-9-3-5-11-6-4-10-15(13)16(11)14/h1-10H

> <INCHI_KEY>
GVEPBJHOBDJJJI-UHFFFAOYSA-N

> <FORMULA>
C16H10

> <MOLECULAR_WEIGHT>
202.2506

> <EXACT_MASS>
202.07825032

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
23.22506007825715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
fluoranthene

> <ALOGPS_LOGP>
5.04

> <JCHEM_LOGP>
4.283927480666667

> <ALOGPS_LOGS>
-6.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
66.72260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fluoranthene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.885   4.915   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.714   0.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.292   4.289   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.714   1.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.639   4.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.380  -0.450   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.453   2.757   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.800   2.478   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.046   0.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.207   1.852   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    8                                                       
CONECT    3    5    9                                                       
CONECT    4    6   10                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    1   12                                                       
CONECT    8    2   13                                                       
CONECT    9    3   14                                                       
CONECT   10    4   15                                                       
CONECT   11    5    6   16                                                  
CONECT   12    7   13   14                                                  
CONECT   13    8   12   15                                                  
CONECT   14    9   12   16                                                  
CONECT   15   10   13   16                                                  
CONECT   16   11   14   15                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   38    0
END

COMPND    HMDB0252354
HETATM    1  C1  UNL     1       3.691   0.555   0.138  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.614  -0.781  -0.240  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.390  -1.391  -0.406  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.226  -0.706  -0.206  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.331   0.629   0.171  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.532   1.276   0.348  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.054   1.083   0.307  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.677   2.275   0.648  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.076   2.357   0.678  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.884   1.278   0.377  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.265   0.085   0.036  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.974  -1.055  -0.283  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.269  -2.211  -0.614  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.890  -2.235  -0.629  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.184  -1.088  -0.307  1.00  0.00           C  
HETATM   16  C16 UNL     1      -0.892   0.033   0.014  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.654   0.989   0.256  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.513  -1.346  -0.405  1.00  0.00           H  
HETATM   19  H3  UNL     1       2.325  -2.430  -0.700  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.584   2.314   0.642  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.050   3.123   0.885  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.534   3.299   0.947  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.938   1.307   0.391  1.00  0.00           H  
HETATM   24  H8  UNL     1      -4.042  -1.101  -0.291  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.791  -3.140  -0.875  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.339  -3.117  -0.881  1.00  0.00           H  
CONECT    1    2    2    6   17
CONECT    2    3   18
CONECT    3    4    4   19
CONECT    4    5   15
CONECT    5    6    6    7
CONECT    6   20
CONECT    7    8    8   16
CONECT    8    9   21
CONECT    9   10   10   22
CONECT   10   11   23
CONECT   11   12   16   16
CONECT   12   13   13   24
CONECT   13   14   25
CONECT   14   15   15   26
CONECT   15   16
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Benzo[JK]fluorene	ChEBI

Chemical Formula

C₁₆H₁₀

Average Molecular Weight

202.2506

Monoisotopic Molecular Weight

202.07825032

IUPAC Name

fluoranthene

Traditional Name

fluoranthene

CAS Registry Number

Not Available

SMILES

C1=CC=C2C(=C1)C1=CC=CC3=C1C2=CC=C3

InChI Identifier

InChI=1S/C16H10/c1-2-8-13-12(7-1)14-9-3-5-11-6-4-10-15(13)16(11)14/h1-10H

InChI Key

GVEPBJHOBDJJJI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Aromatic hydrocarbon
Polycyclic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

ortho- and peri-fused polycyclic arene (CHEBI:33083 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0252354)

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	5.04	ALOGPS
logP	4.28	ChemAxon
logS	-6.3	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.72 m³·mol⁻¹	ChemAxon
Polarizability	23.23 Å³	ChemAxon
Number of Rings	4	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+H]+	150.193	30932474
DeepCCS	[M-H]-	147.798	30932474
DeepCCS	[M-2H]-	181.451	30932474
DeepCCS	[M+Na]+	156.192	30932474
AllCCS	[M+H]+	143.3	32859911
AllCCS	[M+H-H2O]+	139.0	32859911
AllCCS	[M+NH4]+	147.4	32859911
AllCCS	[M+Na]+	148.5	32859911
AllCCS	[M-H]-	148.2	32859911
AllCCS	[M+Na-2H]-	147.1	32859911
AllCCS	[M+HCOO]-	146.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fluoranthene	C1=CC=C2C(=C1)C1=CC=CC3=C1C2=CC=C3	3238.8	Standard polar	33892256
Fluoranthene	C1=CC=C2C(=C1)C1=CC=CC3=C1C2=CC=C3	2035.6	Standard non polar	33892256
Fluoranthene	C1=CC=C2C(=C1)C1=CC=CC3=C1C2=CC=C3	2118.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Fluoranthene GC-MS (Non-derivatized)	splash10-0udi-3590000000-5ab718d6c845c4b1e233	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluoranthene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-0290000000-ec347a3e1f4dea2070be	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluoranthene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-0190000000-b0eb4c94502407be0112	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoranthene 10V, Positive-QTOF	splash10-0udi-0090000000-d7446c72677de15e324d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoranthene 20V, Positive-QTOF	splash10-0udi-0090000000-d7446c72677de15e324d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoranthene 40V, Positive-QTOF	splash10-0udi-0190000000-e551186a60a8bdd9c370	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoranthene 10V, Negative-QTOF	splash10-0udi-0090000000-b8e225a58555792fec89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoranthene 20V, Negative-QTOF	splash10-0udi-0090000000-b8e225a58555792fec89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoranthene 40V, Negative-QTOF	splash10-0udi-0090000000-e236182f2a4045631f86	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoranthene 10V, Positive-QTOF	splash10-0udi-0090000000-d631c56cd3c088dbebc4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoranthene 20V, Positive-QTOF	splash10-0udi-0090000000-d631c56cd3c088dbebc4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoranthene 40V, Positive-QTOF	splash10-0udi-0090000000-d1d130f9bef833b4f7b4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoranthene 10V, Negative-QTOF	splash10-0udi-0090000000-6aba671a40209155866b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoranthene 20V, Negative-QTOF	splash10-0udi-0090000000-6aba671a40209155866b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluoranthene 40V, Negative-QTOF	splash10-0udi-0090000000-6aba671a40209155866b	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

Not Available

KEGG Compound ID

C19425

BioCyc ID

CPD-15564

BiGG ID

Not Available

Wikipedia Link

Fluoranthene

METLIN ID

Not Available

PubChem Compound

9154

PDB ID

Not Available

ChEBI ID

33083

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 Fluoranthene (HMDB0252354)

MOL for HMDB0252354 (Fluoranthene)

3D MOL for HMDB0252354 (Fluoranthene)

3D SDF for HMDB0252354 (Fluoranthene)

3D-SDF for HMDB0252354 (Fluoranthene)

PDB for HMDB0252354 (Fluoranthene)

3D PDB for HMDB0252354 (Fluoranthene)

SMILES for HMDB0252354 (Fluoranthene)

INCHI for HMDB0252354 (Fluoranthene)

Structure for HMDB0252354 (Fluoranthene)

3D Structure for HMDB0252354 (Fluoranthene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra