phenanthrene

Synonyms: "phenanthren", "phenanthrin", "phenanthracene", "ravatite", "phenantrin".

Source: Phenanthrene is produced by incomplete combustion of fossil fuels, and from plant-derived precursors in sediments. Comercially, phenanthrene is used to make dyes, plastics, pesticides, explosives, drugs and steroids

Identifiers:

IUPAC Name: phenanthrene
CAS Number: 85-01-8
PubChem ID: 995
InChiKey: YNPNZTXNASCQKK-UHFFFAOYSA-N
Canonical SMILES: C1=CC=C2C(=C1)C=CC3=CC=CC=C32

Structural Properties:

Molecular Formula: C14H10
Molecular Weight: 178.234

Pharmacophore Features:

Number of bond donors: 0
Number of bond acceptors: 0
Number of atoms different from hydrogen: 14

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Evidence Supporting This Chemical as an Endocrine Disruptor
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Benisek M, Kubincova P, Blaha L, Hilscherova K. 2011. The effects of PAHs and N-PAHs on retinoid signaling and Oct-4 expression in vitro. Toxicol Lett 200(3):169-175. DOI: 10.1016/j.toxlet.2010.11.011. URL: http://www.sciencedirect.com/science/article/pii/S0378427410017716?via%3Dihub.
Evans AD, Nipper M. 2007. Toxicity of phenanthrene and lindane mixtures to marine invertebrates. Environmental Toxicology 22(5):495-501. DOI: 10.1002/tox.20279. URL: http://onlinelibrary.wiley.com/doi/10.1002/tox.20279/abstractIncardona JP, Collier TK, Scholz NL. 2004. Defects in cardiac function precede morphological abnormalities in fish embryos exposed to polycyclic aromatic hydrocarbons. Toxicol Appl Pharmacol 196(2):191-205. DOI: 10.1016/j.taap.2003.11.026. URL: https://www.sciencedirect.com/science/article/pii/S0041008X04000110?via%3Dihub.
Monteiro PRR, Reis-Henriques MA, Coimbra J. 2000. Plasma steroid levels in female flounder (Platichthys flesus) after chronic dietary exposure to single polycyclic aromatic hydrocarbons. Marine Environmental Research 49(5):453-467. DOI: 10.1016/S0141-1136(99)00085-9. URL: https://www.sciencedirect.com/science/article/pii/S0141113699000859.
Monteiro PRR, Reis-Henriques MA, Coimbra J. 2000. Polycyclic aromatic hydrocarbons inhibit in vitro ovarian steroidogenesis in the flounder (Platichthys flesus L.). Aquatic Toxicology 48(4):549-559. DOI: 10.1016/S0166-445X(99)00055-7. URL: https://www.sciencedirect.com/science/article/pii/S0166445X99000557.

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