Phenanthrene

Details

• Internal ID: c61ac45e-d013-4bb3-abd3-51120720c586
• Taxonomy: Benzenoids > Phenanthrenes and derivatives
• IUPAC Name: phenanthrene
• SMILES (Canonical): C1=CC=C2C(=C1)C=CC3=CC=CC=C32
• SMILES (Isomeric): C1=CC=C2C(=C1)C=CC3=CC=CC=C32
• InChI: InChI=1S/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10H
• InChI Key: YNPNZTXNASCQKK-UHFFFAOYSA-N
• Popularity: 15,402 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₀
• Molecular Weight: 178.23 g/mol
• Exact Mass: 178.078250319 g/mol
• Topological Polar Surface Area (TPSA): 0.00 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 3.99
• H-Bond Acceptor: 0
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 85-01-8
• Phenanthren
• Phenanthracene
• Phenanthrin
• Ravatite
• Phenantrin
• Phenanthrene, pure
• Phenanthren [German]
• CCRIS 1233
• HSDB 2166
• EINECS 201-581-5
• UNII-448J8E5BST
• NSC 26256
• NSC-26256
• Phenanthrene-13C2
• 448J8E5BST
• DTXSID6024254
• CHEBI:28851
• AI3-00790
• (3)HELICENE
• CHEMBL46730
• DTXCID904254
• NSC26256
• MFCD00001168
• Coal tar pitch volatiles: phenanthrene
• Phenanthrene 10 microg/mL in Cyclohexane
• Phenanthrene 200 microg/mL in Isooctane
• Phenanthrene 10 microg/mL in Acetonitrile
• Phenanthrene 100 microg/mL in Acetonitrile
• PHENANTHRENE (IARC)
• PHENANTHRENE [IARC]
• CAS-85-01-8
• PEY
• Fenantreno
• Phenanthrene-
• 9-Phenanthrene
• phenanthrene-ring
• Phenanthrene, 98%
• phenanthren, kemisk rent
• Phenanthrene Zone Refined
• PHENANTHRENE [MI]
• 9,10-Dehydrophenanthrene
• bmse000560
• PHENANTHRENE [HSDB]
• MLS002454437
• WLN: L B666J
• HMS2268O22
• HY-B1727
• Tox21_201638
• Tox21_300573
• BDBM50159266
• STL453632
• AKOS008967330
• Phenanthrene (purified by sublimation)
• LS-1845
• Phenanthrene, zone-refined, >=99.5%
• NCGC00091177-01
• NCGC00091177-02
• NCGC00091177-03
• NCGC00091177-04
• NCGC00254398-01
• NCGC00259187-01
• Phenanthrene, sublimed grade, >=99.5%
• AC-11346
• AS-12847
• CID 71309489
• SMR000112025
• CS-0013733
• FT-0631391
• FT-0633623
• FT-0673667
• FT-0673668
• P0079
• P0331
• P1310
• P2877
• EN300-18073
• Phenanthrene Zone Refined (number of passes:30)
• A841054
• Q422037
• 5-Amino-6-chloro-3-pyridinecarboxylicacidmethylester
• W-104097
• Z57139327
• Phenanthrene, certified reference material, TraceCERT(R)
• Phenanthrene, purum, for fluorescence, >=97.0% (HPLC)
• Phenanthrene, analytical standard, for environmental analysis
• InChI=1/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10
• 1173018-81-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9954	99.54%
Caco-2	+	0.8668	86.68%
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	+	0.9658	96.58%
OATP1B3 inhibitior	+	0.9656	96.56%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.5625	56.25%
P-glycoprotein inhibitior	-	0.9637	96.37%
P-glycoprotein substrate	-	0.9944	99.44%
CYP3A4 substrate	-	0.7773	77.73%
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	-	0.9420	94.20%
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	+	0.9967	99.67%
Skin irritation	+	0.9222	92.22%
Skin corrosion	-	0.7730	77.30%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7123	71.23%
Micronuclear	-	0.6024	60.24%
Hepatotoxicity	+	0.8823	88.23%
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	+	0.4687	46.87%
Acute Oral Toxicity (c)	III	0.7913	79.13%
Estrogen receptor binding	+	0.8559	85.59%
Androgen receptor binding	+	0.8613	86.13%
Thyroid receptor binding	+	0.5687	56.87%
Glucocorticoid receptor binding	-	0.4866	48.66%
Aromatase binding	+	0.7239	72.39%
PPAR gamma	+	0.6831	68.31%
Honey bee toxicity	-	0.9392	93.92%
Biodegradation	+	0.5750	57.50%
Crustacea aquatic toxicity	+	0.9800	98.00%
Fish aquatic toxicity	+	0.9750	97.50%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	35481.3 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	39810.7 nM	Potency	via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	1000 nM; 1000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	1995.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.01%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.10%	95.56%
CHEMBL3959	P16083	Quinone reductase 2	82.06%	89.49%

Plants that contains it

• Actaea cimicifuga
• Actaea dahurica
• Actaea simplex
• Arnebia euchroma
• Arnebia guttata
• Bletilla striata
• Buddleja lindleyana
• Cornus officinalis
• Humulus scandens
• Lithospermum erythrorhizon
• Peganum harmala
• Pogostemon cablin
• Pterolobium hexapetalum
• Saxifraga stolonifera
• Trichosanthes rosthornii
• Vitis vinifera

Cross-Links

• PubChem: 995
• NPASS: NPC96835
• ChEMBL: CHEMBL46730
• LOTUS: LTS0089727
• wikiData: Q422037