Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H12 |
| Molecular Weight | 228.2879 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1=CC=C2C(C=CC3=C2C4=CC=CC=C4C=C3)=C1
InChI
InChIKey=TUAHORSUHVUKBD-UHFFFAOYSA-N
InChI=1S/C18H12/c1-3-7-16-13(5-1)9-11-15-12-10-14-6-2-4-8-17(14)18(15)16/h1-12H
| Molecular Formula | C18H12 |
| Molecular Weight | 228.2879 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Polycyclic aromatic hydrocarbons stimulate human CYP3A4 promoter activity via PXR. | 2013-10-24 |
|
| A novel approach for a toxicity prediction model of environmental pollutants by using a quantitative structure-activity relationship method based on toxicogenomics. | 2011 |
|
| Formation and repair of tobacco carcinogen-derived bulky DNA adducts. | 2010-12-20 |
|
| Differential repair of polycyclic aromatic hydrocarbon DNA adducts from an actively transcribed gene. | 2010-09-04 |
|
| Antioxidant airway responses following experimental exposure to wood smoke in man. | 2010-08-20 |
|
| Mutagenicity of an aged gasworks soil during bioslurry treatment. | 2009-06 |
|
| Mutagenicity, stable DNA adducts, and abasic sites induced in Salmonella by phenanthro[3,4-b]- and phenanthro[4,3-b]thiophenes, sulfur analogs of benzo[c]phenanthrene. | 2009-02-10 |
|
| Sensing polycyclic aromatic hydrocarbons with dithiocarbamate-functionalized ag nanoparticles by surface-enhanced Raman scattering. | 2009-02-01 |
|
| Ab initio and experimental studies on structure and vibrational spectra of some partially reduced benzo[c]phenanthrenes. | 2009-02 |
|
| 3'-Intercalation of a N2-dG 1R-trans-anti-benzo[c]phenanthrene DNA adduct in an iterated (CG)3 repeat. | 2008-07 |
|
| Concentration and profile of 22 urinary polycyclic aromatic hydrocarbon metabolites in the US population. | 2008-07 |
|
| Fjord-region benzo[g]chrysene-11,12-dihydrodiol and benzo[c]phenanthrene-3,4-dihydrodiol as substrates for rat liver dihydrodiol dehydrogenase (AKR1C9): structural basis for stereochemical preference. | 2008-03 |
|
| Synthetic, crystallographic, computational, and biological studies of 1,4-difluorobenzo[c]phenanthrene and its metabolites. | 2007-09-28 |
|
| Palladium-catalyzed synthesis of nucleoside adducts from bay- and fjord-region diol epoxides. | 2007-07-06 |
|
| Structure/reactivity relationships in the benzo[c]phenanthrene skeleton: stable ion and electrophilic substitution (nitration, bromination) study of substituted analogues, novel carbocations and substituted derivatives. | 2007-04-27 |
|
| Intercalating polycyclic aromatic hydrocarbon-DNA adducts poison DNA religation by Vaccinia topoisomerase and act as roadblocks to digestion by exonuclease III. | 2006-06-20 |
|
| Reference range levels of polycyclic aromatic hydrocarbons in the US population by measurement of urinary monohydroxy metabolites. | 2006-03 |
|
| Novel synthesis of benzalacetone analogues of naphth[a]azulenes by intramolecular tropylium ion-mediated furan ring-opening reaction and X-ray investigation of a naphth[1,2-a]azulene derivative. | 2005-10-28 |
|
| Cyclodehydrogenation reactions to cyclopentafused polycyclic aromatic hydrocarbons. | 2005-09-01 |
|
| Surface-enhanced micro-Raman detection and characterization of calix[4]arene-polycyclic aromatic hydrocarbon host-guest complexes. | 2005-08 |
|
| Accommodation of a 1S-(-)-benzo[c]phenanthrenyl-N6-dA adduct in the Y-family Dpo4 DNA polymerase active site: structural insights through molecular dynamics simulations. | 2005-03 |
|
| Role of cytochrome p4501 family members in the metabolic activation of polycyclic aromatic hydrocarbons in mouse epidermis. | 2004-12 |
|
| Conformational searches elucidate effects of stereochemistry on structures of deoxyadenosine covalently bound to tumorigenic metabolites of benzo[C] phenanthrene. | 2004-09-01 |
|
| Benzo[c]phenanthrene adducts and nogalamycin inhibit DNA transesterification by vaccinia topoisomerase. | 2004-05-28 |
|
| Selective detection of monohydroxy metabolites of polycyclic aromatic hydrocarbons in urine using liquid chromatography/triple quadrupole tandem mass spectrometry. | 2004 |
|
| Inhibition of Werner syndrome helicase activity by benzo[c]phenanthrene diol epoxide dA adducts in DNA is both strand-and stereoisomer-dependent. | 2003-10-17 |
|
| Nanotubes: number of Kekulé structures and aromaticity. | 2003-03-26 |
|
| Site-specific mutagenesis in Escherichia coli by N2-deoxyguanosine adducts derived from the highly carcinogenic fjord-region benzo[c]phenanthrene 3,4-diol 1,2-epoxides. | 2002-12 |
|
| Thermodynamic and structural factors in the removal of bulky DNA adducts by the nucleotide excision repair machinery. | 2002-11-05 |
|
| Novel stereoselective control over cis vs trans opening of benzo[c]phenanthrene 3,4-diol 1,2-epoxides by the exocyclic N(2)-amino group of deoxyguanosine in the presence of hexafluoropropan-2-ol. | 2002-09-20 |
|
| Benzo[a]pyrene and benz[c]phenanthrene: the effect of structure on the binding of water molecules to the diol epoxides. | 2002-08 |
|
| Different effects on human topoisomerase I by minor groove and intercalated deoxyguanosine adducts derived from two polycyclic aromatic hydrocarbon diol epoxides at or near a normal cleavage site. | 2002-04-19 |
|
| Synthesis and characterization of site-specific and stereoisomeric fjord dibenzo[a,l]pyrene diol epoxide-N(6)-adenine adducts: unusual thermal stabilization of modified DNA duplexes. | 2002-02 |
|
| Characterization of DNA adducts derived from syn-benzo[ghi]fluoranthene-3,4-dihydrodiol-5,5a-epoxide and comparative DNA binding studies with structurally-related anti-diolepoxides of benzo[ghi]fluoranthene and benzo[c]phenanthrene. | 2002-02 |
|
| Quantification of monohydroxy-PAH metabolites in urine by solid-phase extraction with isotope dilution-GC-MS. | 2002-01 |
|
| Characterization of a major aromatic DNA adduct detected in human breast tissues. | 2002 |
|
| Tobacco smoke carcinogens and breast cancer. | 2002 |
|
| Cyclohexene ring and Fjord region twist inversion in stereoisomeric DNA adducts of enantiomeric benzo[c]phenanthrene diol epoxides. | 2001-12 |
|
| Patterns of resistance to exonuclease digestion of oligonucleotides containing polycyclic aromatic hydrocarbon diol epoxide adducts at N6 of deoxyadenosine. | 2001-09 |
|
| Metabolic activation of polycyclic aromatic hydrocarbons and other procarcinogens by cytochromes P450 1A1 and P450 1B1 allelic variants and other human cytochromes P450 in Salmonella typhimurium NM2009. | 2001-09 |
|
| Role of arginine 216 in catalytic activity of murine Alpha class glutathione transferases mGSTAl-1 and mGSTA2-2 toward carcinogenic diol epoxides of polycyclic aromatic hydrocarbons. | 2001-08 |
|
| Metabolic activation of benzo[c]phenanthrene by cytochrome P450 enzymes in human liver and lung. | 2001-06 |
|
| Substituent effects and charge delocalization mode in chrysenium, benzo[c]phenanthrenium, and benzo[g]chrysenium cations: a stable ion and electrophilic substitution study. | 2001-02-09 |
|
| Dose-dependent differences in the profile of mutations induced by carcinogenic (R,S,S,R) bay- and fjord-region diol epoxides of polycyclic aromatic hydrocarbons. | 2001 |
|
| Catalytic efficiencies of allelic variants of human glutathione S-transferase P1-1 toward carcinogenic anti-diol epoxides of benzo[c]phenanthrene and benzo[g]chrysene. | 1998-12-01 |
|
| Glutathione conjugation of bay- and fjord-region diol epoxides of polycyclic aromatic hydrocarbons by glutathione transferases M1-1 and P1-1. | 1997-11 |
|
| Role of the Ha-ras gene in the malignant transformation of rat liver oval cells. | 1997-05-16 |
|
| Role of cytochrome P450 enzyme induction in the metabolic activation of benzo[c]phenanthrene in human cell lines and mouse epidermis. | 1997-05 |
|
| Stereoselective epoxidation and hydration at the K-region of polycyclic aromatic hydrocarbons by cDNA-expressed cytochromes P450 1A1, 1A2, and epoxide hydrolase. | 1996-12-10 |
|
| Contrasting incidence of ras mutations in rat mammary and mouse skin tumors induced by anti-benzo[c]phenanthrene-3,4-diol-1,2-epoxide. | 1994-10 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:45:43 GMT 2025
by
admin
on
Mon Mar 31 18:45:43 GMT 2025
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| Record UNII |
H22XVR3V8A
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| Record Status |
Validated (UNII)
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| Record Version |
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H22XVR3V8A
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205-896-9
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9136
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BENZO(C)PHENANTHRENE
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DTXSID4075459
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82292
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C002615
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m2390
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195-19-7
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