Benzo[a]pyrene

Details

• Internal ID: 006caa18-6061-4a17-9b1e-52aef9b0f644
• Taxonomy: Benzenoids > Pyrenes > Benzopyrenes
• IUPAC Name: benzo[a]pyrene
• SMILES (Canonical): C1=CC=C2C3=C4C(=CC2=C1)C=CC5=C4C(=CC=C5)C=C3
• SMILES (Isomeric): C1=CC=C2C3=C4C(=CC2=C1)C=CC5=C4C(=CC=C5)C=C3
• InChI: InChI=1S/C20H12/c1-2-7-17-15(4-1)12-16-9-8-13-5-3-6-14-10-11-18(17)20(16)19(13)14/h1-12H
• InChI Key: FMMWHPNWAFZXNH-UHFFFAOYSA-N
• Popularity: 22,100 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₂
• Molecular Weight: 252.30 g/mol
• Exact Mass: 252.093900383 g/mol
• Topological Polar Surface Area (TPSA): 0.00 Ų
• XlogP: 6.00
• Atomic LogP (AlogP): 5.74
• H-Bond Acceptor: 0
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 50-32-8
• 3,4-Benzopyrene
• benzo[pqr]tetraphene
• BENZO(A)PYRENE
• 3,4-Benzpyrene
• benzo[def]chrysene
• Benzpyrene
• 6,7-Benzopyrene
• 3,4-BP
• Benz[a]pyrene
• 3,4-Benz[a]pyrene
• 3,4-Benzopirene
• 3,4-Benzpyren
• Benzopyrene
• B(a)P
• Benz(a)pyrene
• Benzo(d,e,f)chrysene
• 3,4-Benz(a)pyrene
• 3,4 Benzpyrene
• (B(a)P)
• RCRA waste number U022
• Benzo[d,e,f]chrysene
• 3,4-Benzo(a)pyrene
• B[a]p
• NSC 21914
• 3,4 Benzopyrene
• Benzo(def)chrysene
• 3,4-benzylpyrene
• BP
• CCRIS 76
• CHEBI:29865
• HSDB 2554
• 3,4-Benzpyren [German]
• Benzo[A]-Pyrene
• 3,4-Benzypyrene
• EINECS 200-028-5
• 3,4-Benzopirene [Italian]
• UNII-3417WMA06D
• DTXSID2020139
• AI3-50461
• 3417WMA06D
• Benzo[a]pyrene (BaP)
• C20H12
• NSC-21914
• RCRA waste no. U022
• Benzo(a)pyrene radical cation
• CHEMBL31184
• DTXCID40139
• Benzo(a)pyrene, radical ion(1+)
• Benzo(a)pyrene, radical ion(1-)
• NSC21914
• benzo(pqr)tetraphene
• Benzo(a)pyrene, labeled with tritium
• MFCD00003602
• Benzo(3,4)pyrene, radical ion(1+)
• 42299-33-2
• BENZO(A)PYRENE-7 8-D2 98
• Coal tar pitch volatiles: benzo(a)pyrene
• 6699-27-0
• BENZO(A)PYRENE (IARC)
• BENZO(A)PYRENE [IARC]
• 34505-58-3
• Benzopireno
• Benzo [a] pireno
• Benzo[d,f]chrysene
• 6,7-Benzpyren
• Benzo Pyrene[BAP]
• Spectrum_001871
• SpecPlus_000953
• Spectrum2_001081
• Spectrum3_001695
• Spectrum4_000609
• Spectrum5_001824
• Epitope ID:117721
• Benzo(a)pyrene {B(a)P}
• BENZO(A)PYRENE [MI]
• BSPBio_003250
• KBioGR_001138
• KBioSS_002390
• MLS002695983
• BIDD:ER0497
• DivK1c_007049
• SPBio_001122
• 3,4-Benzopyrene (carcinogen)
• BENZO(A)PYRENE [HSDB]
• KBio1_001993
• KBio2_002385
• KBio2_004953
• KBio2_007521
• KBio3_002470
• HMS3089C04
• HMS3746C17
• benzo[a]pyrene; benzo[def]chrysene
• Benzo[a]pyrene, >=96% (HPLC)
• Tox21_200710
• 3,4-BENZPYRENE (CARCINOGEN)
• BDBM50137506
• CCG-39759
• LS-139
• AKOS015907666
• AM61580
• CS-7789
• CS-T-05163
• CAS-50-32-8
• WLN: L D6 B6666 2AB TJ
• NCGC00178185-01
• NCGC00178185-02
• NCGC00258264-01
• NCI60_001824
• SMR000393676
• SY048151
• 3,4-Benzopyrene (purified by sublimation)
• Benzo(a)pyrene; (Coal tar pitch volatiles)
• Benzo[a]pyrene 1000 microg/mL in Acetone
• HY-107377
• B0085
• Benzo(a)pyrene; (Coal tar pitch volatiles)
• Benzo[a]pyrene 10 microg/mL in Acetonitrile
• FT-0614185
• Benzo[a]pyrene 100 microg/mL in Acetonitrile
• Benzo[a]pyrene 100 microg/mL in Cyclohexane
• C07535
• A828066
• A828067
• Benzo[a]pyrene, vial of 1 g, analytical standard
• Q306051
• BRD-K09668667-001-02-0
• Benzo[a]pyrene, certified reference material, TraceCERT(R)
• Benzo[a]pyrene, analytical standard, for environmental analysis
• BENZO(A)PYRENE (SEE ALSO: BENZO(E)PYRENE (CAS 192-97-2))

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9954	99.54%
Caco-2	+	0.8289	82.89%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Lysosomes	0.8244	82.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9503	95.03%
OATP1B3 inhibitior	+	0.9656	96.56%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8250	82.50%
P-glycoprotein inhibitior	-	0.8699	86.99%
P-glycoprotein substrate	-	0.9479	94.79%
CYP3A4 substrate	-	0.6764	67.64%
CYP2C9 substrate	-	0.8036	80.36%
CYP2D6 substrate	+	0.3525	35.25%
CYP3A4 inhibition	-	0.9288	92.88%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.8548	85.48%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.6798	67.98%
CYP2C8 inhibition	-	0.5938	59.38%
CYP inhibitory promiscuity	+	0.5335	53.35%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5700	57.00%
Carcinogenicity (trinary)	Warning	0.4954	49.54%
Eye corrosion	+	0.6689	66.89%
Eye irritation	+	0.9863	98.63%
Skin irritation	+	0.9222	92.22%
Skin corrosion	-	0.7730	77.30%
Ames mutagenesis	+	1.0000	100.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6231	62.31%
Micronuclear	-	0.6024	60.24%
Hepatotoxicity	+	0.9250	92.50%
skin sensitisation	+	0.9334	93.34%
Respiratory toxicity	-	0.8889	88.89%
Reproductive toxicity	-	0.8778	87.78%
Mitochondrial toxicity	-	0.9875	98.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.7913	79.13%
Estrogen receptor binding	+	0.9693	96.93%
Androgen receptor binding	+	0.9310	93.10%
Thyroid receptor binding	+	0.8570	85.70%
Glucocorticoid receptor binding	+	0.9045	90.45%
Aromatase binding	+	0.9467	94.67%
PPAR gamma	+	0.9060	90.60%
Honey bee toxicity	-	0.8701	87.01%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	1.0000	100.00%
Fish aquatic toxicity	+	0.9750	97.50%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	28000 nM	IC50	via CMAUP
CHEMBL3201	P35869	Aryl hydrocarbon receptor	2700 nM; 5 nM	EC50; EC50	PMID: 20060304; PMID: 14684315
CHEMBL3356	P05177	Cytochrome P450 1A2	40 nM	IC50	via CMAUP
CHEMBL1951	P21397	Monoamine oxidase A	5972 nM	IC50	via CMAUP
CHEMBL1824	P04626	Receptor protein-tyrosine kinase erbB-2	41503 nM	IC50	via CMAUP
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	26235 nM	IC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.55%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.97%	95.56%
CHEMBL240	Q12809	HERG	89.74%	89.76%
CHEMBL2535	P11166	Glucose transporter	86.63%	98.75%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	85.80%	96.42%
CHEMBL3959	P16083	Quinone reductase 2	84.42%	89.49%
CHEMBL1951	P21397	Monoamine oxidase A	82.77%	91.49%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.60%	96.67%
CHEMBL3401	O75469	Pregnane X receptor	81.35%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.97%	86.33%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	80.35%	92.08%

Plants that contains it

• Angelica sinensis
• Helianthus annuus

Cross-Links

• PubChem: 2336
• NPASS: NPC50063
• ChEMBL: CHEMBL31184
• LOTUS: LTS0143131
• wikiData: Q306051