Pyrene

Details

• Internal ID: 77634621-0dfd-4b3b-8624-497d0171549c
• Taxonomy: Benzenoids > Pyrenes
• IUPAC Name: pyrene
• SMILES (Canonical): C1=CC2=C3C(=C1)C=CC4=CC=CC(=C43)C=C2
• SMILES (Isomeric): C1=CC2=C3C(=C1)C=CC4=CC=CC(=C43)C=C2
• InChI: InChI=1S/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H
• InChI Key: BBEAQIROQSPTKN-UHFFFAOYSA-N
• Popularity: 18,835 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₀
• Molecular Weight: 202.25 g/mol
• Exact Mass: 202.078250319 g/mol
• Topological Polar Surface Area (TPSA): 0.00 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 4.58
• H-Bond Acceptor: 0
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 129-00-0
• Benzo[def]phenanthrene
• Pyren
• beta-Pyrene
• Benzo(def)phenanthrene
• .beta.-Pyrene
• Pyren [German]
• CCRIS 1256
• Pireno
• CHEBI:39106
• HSDB 4023
• EINECS 204-927-3
• UNII-9E0T7WFW93
• NSC 17534
• 9E0T7WFW93
• Coal tar pitch volatiles:pyrene
• DTXSID3024289
• Pyrene-13C6
• AI3-23977
• Pyrene[def]phenanthrene
• NSC-17534
• NSC-66449
• 1346601-04-4
• CHEMBL279564
• DTXCID804289
• Coal tar pitch volatiles: pyrene
• EC 204-927-3
• NSC17534
• Pyrene sublimed grade
• 1228182-40-8
• NCGC00090910-03
• PYRENE (IARC)
• PYRENE [IARC]
• 41496-25-7
• Pyrne
• beta-Pyrine
• Pyrene, Powder
• Pyren(GERMAN)
• MFCD00004136
• Pyrene, 98%
• PYRENE [HSDB]
• benzo(d,e,f)phenanthrene
• {Benzo[def]phenanthrene}
• PYRENE [MI]
• Epitope ID:119715
• Pyrene, analytical standard
• Pyrene, crystalline, 95%
• Benzo (d,e,f) phenanthrene
• Pyrene (ACD/Name 4.0)
• BIDD:ER0347
• Pyrene, sublimed grade, 99%
• Pyrene (purified by sublimation)
• HMS3749I11
• CS-B1735
• NSC66449
• WLN: L666 B6 2AB PJ
• Pyrene 10 microg/mL in Cyclohexane
• Tox21_400063
• BDBM50214608
• LS-719
• Pyrene 10 microg/mL in Acetonitrile
• STL570454
• AKOS000269680
• Pyrene 100 microg/mL in Acetonitrile
• NCGC00090910-01
• NCGC00090910-02
• NCGC00090910-04
• AS-13613
• CAS-129-00-0
• HY-103609
• FT-0622695
• FT-0674169
• P1104
• P2072
• Pyrene, BCR(R) certified Reference Material
• EN300-174930
• A805889
• AB-131/40897138
• Pyrene, purum, for fluorescence, >=97.0% (GC)
• Q415723
• Pyrene, certified reference material, TraceCERT(R)
• Q-201641
• Z57901968
• Pyrene, puriss. p.a., for fluorescence, >=99.0% (GC)
• Pyrene, certified reference material, 1000 mug/mL in methanol
• 8P0
• InChI=1/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9954	99.54%
Caco-2	+	0.8773	87.73%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Lysosomes	0.8244	82.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9774	97.74%
OATP1B3 inhibitior	+	0.9656	96.56%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.6256	62.56%
P-glycoprotein inhibitior	-	0.9232	92.32%
P-glycoprotein substrate	-	0.9932	99.32%
CYP3A4 substrate	-	0.8529	85.29%
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	-	0.9561	95.61%
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	+	0.9925	99.25%
Skin irritation	+	0.9222	92.22%
Skin corrosion	-	0.7730	77.30%
Ames mutagenesis	+	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7316	73.16%
Micronuclear	-	0.6024	60.24%
Hepatotoxicity	+	0.9125	91.25%
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	+	0.6432	64.32%
Acute Oral Toxicity (c)	III	0.7913	79.13%
Estrogen receptor binding	+	0.9197	91.97%
Androgen receptor binding	+	0.7977	79.77%
Thyroid receptor binding	+	0.7123	71.23%
Glucocorticoid receptor binding	+	0.7638	76.38%
Aromatase binding	+	0.7785	77.85%
PPAR gamma	+	0.7537	75.37%
Honey bee toxicity	-	0.9425	94.25%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.9000	90.00%
Fish aquatic toxicity	+	0.9750	97.50%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	12589.3 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	28183.8 nM	Potency	via CMAUP
CHEMBL2231	P04798	Cytochrome P450 1A1	41 nM	IC50	PMID: 17544277
CHEMBL3356	P05177	Cytochrome P450 1A2	7 nM	IC50	PMID: 17544277
CHEMBL4878	Q16678	Cytochrome P450 1B1	2 nM; 2 nM	IC50; IC50	PMID: 17544277; via Super-PRED
CHEMBL340	P08684	Cytochrome P450 3A4	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3959	P16083	Quinone reductase 2	89.86%	89.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.65%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.35%	91.11%

Plants that contains it

• Angelica dahurica
• Atractylodes lancea
• Atractylodes macrocephala

Cross-Links

• PubChem: 31423
• NPASS: NPC245896
• ChEMBL: CHEMBL279564