2,3-bis(4-hydroxyphenyl)propionitrile - Ontology Report - Rat Genome Database

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The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:	2,3-bis(4-hydroxyphenyl)propionitrile	go back to main search page
Accession:	CHEBI:63949	browse the term
Definition:	A nitrile that is acetonitrile in which one of the hydrogens is replaced by a 4-hydroxyphenyl group while a second hydrogen is replaced by a 4-hydroxybenzyl group. It is a specific agonist for estrogen receptor beta (ERbeta).
Synonyms:	exact_synonym:	2,3-BHPPN ; 2,3-bis(4-hydroxyphenyl)propanenitrile; DPN compound
	related_synonym:	2,3-bis(p-hydroxyphenyl)propionitrile; Formula=C15H13NO2; InChI=1S/C15H13NO2/c16-10-13(12-3-7-15(18)8-4-12)9-11-1-5-14(17)6-2-11/h1-8,13,17-18H,9H2; InChIKey=GHZHWDWADLAOIQ-UHFFFAOYSA-N; SMILES=Oc1ccc(CC(C#N)c2ccc(O)cc2)cc1
	alt_id:	MESH:C486182
	xref:	CAS:1428-67-7; LINCS:LSM-1423
	xref_mesh:	MESH:C486182
	xref:	PMID:21268084; PMID:21397017; PMID:21636213; PMID:21712365; Reaxys:3337109

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Genes (46)

2,3-bis(4-hydroxyphenyl)propionitrile

term browser

Symbol

Object Name

Qualifiers

Evidence

Notes

Source

PubMed Reference(s)

RGD Reference(s)

Position

G

aryl hydrocarbon receptor

multiple interactions

[2,3-bis(4-hydroxyphenyl)-propionitrile results in increased activity of AHR protein] which results in increased expression of CYP1A1 mRNA

NCBI chr 6:52,234,089...52,271,568
Ensembl chr 6:52,234,089...52,271,568

G

AKT serine/threonine kinase 1

multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [TGFA protein results in increased phosphorylation of AKT1 protein]

NCBI chr 6:131,713,716...131,735,319
Ensembl chr 6:131,713,720...131,733,921

G

apolipoprotein D

decreases expression

2,3-bis(4-hydroxyphenyl)-propionitrile results in decreased expression of APOD mRNA

NCBI chr11:69,431,261...69,452,306
Ensembl chr11:69,431,260...69,452,305

G

BCL2, apoptosis regulator

increases expression
multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of BCL2 mRNA; 2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of BCL2 protein
ESR1 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of BCL2 protein]; ESR2 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of BCL2 mRNA]
2,3-bis(4-hydroxyphenyl)-propionitrile promotes the reaction [Chlorodiphenyl (54% Chlorine) results in decreased expression of BCL2 protein]

PMID:19264808 PMID:24216299

NCBI chr13:22,689,783...22,853,920
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743

G

caspase 3

multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile promotes the reaction [Chlorodiphenyl (54% Chlorine) results in increased activity of CASP3 protein]; 2,3-bis(4-hydroxyphenyl)-propionitrile promotes the reaction [perfluorooctane sulfonic acid results in increased cleavage of CASP3 protein]

PMID:24216299 PMID:34303733

NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648

G

cyclin D1

multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile promotes the reaction [Chlorodiphenyl (54% Chlorine) results in decreased expression of CCND1 protein]; 2,3-bis(4-hydroxyphenyl)-propionitrile promotes the reaction [perfluorooctane sulfonic acid results in decreased expression of CCND1 protein]

PMID:24216299 PMID:34303733

NCBI chr 1:200,089,002...200,098,524
Ensembl chr 1:200,089,002...200,098,602

G

catenin beta 1

multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [Estrogens deficiency results in decreased expression of CTNNB1 mRNA]

NCBI chr 8:120,640,008...120,667,110
Ensembl chr 8:120,639,995...120,667,111

G

cytochrome P450, family 1, subfamily a, polypeptide 1

multiple interactions
increases expression

[2,3-bis(4-hydroxyphenyl)-propionitrile results in increased activity of AHR protein] which results in increased expression of CYP1A1 mRNA
2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of CYP1A1 mRNA

NCBI chr 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125

G

24-dehydrocholesterol reductase

increases expression

2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of DHCR24 mRNA

NCBI chr 5:121,344,552...121,371,124
Ensembl chr 5:121,344,575...121,371,137

G

desert hedgehog signaling molecule

decreases expression

2,3-bis(4-hydroxyphenyl)-propionitrile results in decreased expression of DHH mRNA

NCBI chr 7:130,050,910...130,056,406
Ensembl chr 7:130,050,910...130,056,406

G

estrogen receptor 1

multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile binds to and results in increased activity of ESR1 protein; ESR1 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of BCL2 protein]; ESR1 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PDCD4 protein]; ESR1 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PTEN protein]

PMID:19264808 PMID:24425189

NCBI chr 1:41,106,335...41,499,104
Ensembl chr 1:41,210,475...41,495,002

G

estrogen receptor 2

increases activity
multiple interactions
increases expression
affects localization
affects response to substance
affects binding

2,3-bis(4-hydroxyphenyl)-propionitrile results in increased activity of ESR2 protein
2,3-bis(4-hydroxyphenyl)-propionitrile binds to and results in increased activity of ESR2 protein; [2,3-bis(4-hydroxyphenyl)-propionitrile binds to and results in increased activity of ESR2 protein] which results in increased secretion of Bicarbonates; ESR2 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of SOD2 protein]; ESR2 protein alternative form inhibits the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of ESR2 protein]
2,3-bis(4-hydroxyphenyl)-propionitrile binds to and results in increased activity of ESR2 protein; 2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [KAT5 protein results in decreased activity of ESR2 protein]; 2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [KAT5 protein results in increased activity of ESR2 protein]; 2,3-bis(4-hydroxyphenyl)-propionitrile results in increased phosphorylation of and results in increased localization of and results in increased activity of ESR2 protein; dicyclohexyl phthalate inhibits the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased activity of ESR2 protein]; ESR2 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of BCL2 mRNA]; ESR2 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PDCD4 mRNA]; Fulvestrant inhibits the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased activity of ESR2 protein]
2,3-bis(4-hydroxyphenyl)-propionitrile binds to and results in increased activity of ESR2 protein; 2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [Estrogens deficiency results in increased expression of ESR2 protein alternative form]; [2,3-bis(4-hydroxyphenyl)-propionitrile binds to and results in increased activity of ESR2 protein] inhibits the reaction [Resveratrol results in decreased expression of PRL protein]; [2,3-bis(4-hydroxyphenyl)-propionitrile binds to and results in increased activity of ESR2 protein] which results in increased expression of SLC1A2 protein
2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of ESR2 mRNA; 2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of ESR2 protein; 2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of ESR2 protein alternative form
2,3-bis(4-hydroxyphenyl)-propionitrile affects the localization of ESR2 protein
ESR2 protein affects the susceptibility to 2,3-bis(4-hydroxyphenyl)-propionitrile
2,3-bis(4-hydroxyphenyl)-propionitrile binds to ESR2 protein

PMID:15236189 PMID:15585566 PMID:15910780 PMID:17935960 PMID:18499763 More...

NCBI chr 6:94,858,438...94,909,630
Ensembl chr 6:94,809,547...94,908,919

G

F11 receptor

multiple interactions
increases expression

Fulvestrant inhibits the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of F11R mRNA]; Fulvestrant inhibits the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of F11R protein]
2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of F11R mRNA; 2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of F11R protein

NCBI chr13:83,873,797...83,897,388
Ensembl chr13:83,873,797...83,897,402

G

Indian hedgehog signaling molecule

decreases expression

2,3-bis(4-hydroxyphenyl)-propionitrile results in decreased expression of IHH mRNA

NCBI chr 9:76,504,315...76,510,532
Ensembl chr 9:76,504,315...76,510,532

G

interleukin 12A

multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [Lipopolysaccharides results in increased expression of IL12A protein]

NCBI chr 2:152,965,769...152,973,035
Ensembl chr 2:152,965,769...152,972,734

G

interleukin 1 alpha

multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [Lipopolysaccharides results in increased secretion of IL1A protein]

NCBI chr 3:116,526,601...116,537,055
Ensembl chr 3:116,526,604...116,536,822

G

interleukin 1 beta

multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [Lipopolysaccharides results in increased secretion of IL1B protein]

NCBI chr 3:116,577,005...116,583,386
Ensembl chr 3:116,577,010...116,583,415

G

interleukin 33

multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [Toluene 2,4-Diisocyanate results in increased expression of IL33 protein]; [2,3-bis(4-hydroxyphenyl)-propionitrile co-treated with Toluene 2,4-Diisocyanate] results in increased expression of IL33 protein
[Lipopolysaccharides co-treated with 2,3-bis(4-hydroxyphenyl)-propionitrile] results in increased expression of IL33 protein

PMID:30017638 PMID:30445053

NCBI chr 1:227,701,964...227,736,374
Ensembl chr 1:227,721,435...227,736,373

G

lysine acetyltransferase 5

multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [KAT5 protein results in decreased activity of ESR2 protein]; 2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [KAT5 protein results in increased activity of ESR2 protein]

NCBI chr 1:202,895,751...202,903,178
Ensembl chr 1:202,895,751...202,903,458

G

mitogen activated protein kinase 1

affects phosphorylation
multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile affects the phosphorylation of MAPK1 protein
2,3-bis(4-hydroxyphenyl)-propionitrile promotes the reaction [perfluorooctane sulfonic acid results in decreased phosphorylation of MAPK1 protein]

PMID:20870566 PMID:34303733

NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616

G

mitogen activated protein kinase 3

affects phosphorylation
multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile affects the phosphorylation of MAPK3 protein
2,3-bis(4-hydroxyphenyl)-propionitrile promotes the reaction [perfluorooctane sulfonic acid results in decreased phosphorylation of MAPK3 protein]

PMID:20870566 PMID:34303733

NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863

G

microRNA 21

decreases expression

2,3-bis(4-hydroxyphenyl)-propionitrile results in decreased expression of MIR21 mRNA

NCBI chr10:71,405,257...71,405,348
Ensembl chr10:71,405,257...71,405,348

G

mitochondrially encoded cytochrome c oxidase I

increases expression

2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of COX1 protein

NCBI chr MT:5,323...6,867
NCBI chr MT:5,323...6,867
NCBI chr MT:5,323...6,867
NCBI chr MT:5,323...6,867
NCBI chr MT:5,323...6,867
NCBI chr MT:5,323...6,867
NCBI chr MT:5,323...6,867
NCBI chr MT:5,323...6,867
NCBI chr MT:5,323...6,867
NCBI chr MT:5,323...6,867
Ensembl chr MT:5,323...6,867

G

nuclear respiratory factor 1

increases expression

2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of NRF1 mRNA

NCBI chr 4:58,664,932...58,772,328
Ensembl chr 4:58,664,957...58,825,328

G

occludin

multiple interactions
increases expression

Fulvestrant inhibits the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of OCLN mRNA]; Fulvestrant inhibits the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of OCLN protein]
2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of OCLN mRNA; 2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of OCLN protein

NCBI chr 2:31,657,217...31,707,466
Ensembl chr 2:31,657,220...31,764,150

G

programmed cell death 4

increases expression
decreases expression
multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PDCD4 protein
2,3-bis(4-hydroxyphenyl)-propionitrile results in decreased expression of PDCD4 mRNA
ESR1 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PDCD4 protein]; ESR2 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PDCD4 mRNA]

NCBI chr 1:252,921,342...252,944,278
Ensembl chr 1:252,921,392...252,944,275

G

proopiomelanocortin

multiple interactions

[4,4',4''-(4-propyl-((1)H)-pyrazole-1,3,5-triyl) tris-phenol co-treated with 2,3-bis(4-hydroxyphenyl)-propionitrile] results in decreased expression of POMC mRNA

NCBI chr 6:26,939,844...26,945,666
Ensembl chr 6:26,939,837...26,945,664

G

peroxiredoxin 5

increases expression

2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PRDX5 protein

NCBI chr 1:204,099,826...204,103,589
Ensembl chr 1:204,099,826...204,114,268

G

prolactin

multiple interactions

[2,3-bis(4-hydroxyphenyl)-propionitrile binds to and results in increased activity of ESR2 protein] inhibits the reaction [resveratrol results in decreased expression of PRL protein]

NCBI chr17:37,859,999...37,870,062
Ensembl chr17:37,860,007...37,870,062

G

phosphatase and tensin homolog

increases expression
multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PTEN protein
ESR1 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of PTEN protein]

NCBI chr 1:230,630,443...230,697,070
Ensembl chr 1:230,630,338...230,696,838

G

prostaglandin E receptor 2

decreases expression

2,3-bis(4-hydroxyphenyl)-propionitrile results in decreased expression of PTGER2 mRNA

NCBI chr15:18,215,013...18,228,714
Ensembl chr15:18,217,285...18,228,714

G

prostaglandin E receptor 4

decreases expression

2,3-bis(4-hydroxyphenyl)-propionitrile results in decreased expression of PTGER4 mRNA

NCBI chr 2:54,330,563...54,347,451
Ensembl chr 2:54,335,424...54,346,670

G

prostaglandin-endoperoxide synthase 2

multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [Lipopolysaccharides results in increased secretion of PTGS2 protein]

NCBI chr13:62,163,936...62,172,193
Ensembl chr13:62,163,932...62,172,188

G

regulator of G-protein signaling 9

multiple interactions

[Amphetamine co-treated with 2,3-bis(4-hydroxyphenyl)-propionitrile] results in decreased expression of RGS9 mRNA

NCBI chr10:94,195,265...94,270,892
Ensembl chr10:94,197,054...94,270,892

G

ryanodine receptor 2

increases phosphorylation

2,3-bis(4-hydroxyphenyl)-propionitrile results in increased phosphorylation of RYR2 protein

NCBI chr17:58,389,925...58,975,641
Ensembl chr17:58,389,925...58,975,142

G

solute carrier family 1 member 2

multiple interactions

2-(2-amino-3-methoxyphenyl)-4H-1-benzopyran-4-one inhibits the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of SLC1A2 protein]; 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of SLC1A2 protein]; [2,3-bis(4-hydroxyphenyl)-propionitrile binds to and results in increased activity of ESR2 protein] which results in increased expression of SLC1A2 protein; Fulvestrant inhibits the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of SLC1A2 protein]; RTKI cpd inhibits the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of SLC1A2 protein]

NCBI chr 3:89,005,129...89,135,469
Ensembl chr 3:89,005,129...89,126,498

G

superoxide dismutase 2

multiple interactions
increases expression

2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [[Oxygen deficiency co-treated with Oxygen] results in decreased activity of SOD2 protein]
2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [4,4',4''-(4-propyl-((1)H)-pyrazole-1,3,5-triyl) tris-phenol inhibits the reaction [Glucose results in decreased expression of SOD2 protein]]
2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of SOD2 protein
ESR2 protein affects the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of SOD2 protein]

PMID:20962025 PMID:21215799 PMID:23526725 PMID:24465521

NCBI chr 1:47,638,318...47,645,163
Ensembl chr 1:47,636,528...47,645,189

G

serine and arginine rich splicing factor 7

multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [Estrogens deficiency results in decreased expression of SRSF7 mRNA]

NCBI chr 6:14,811,775...14,818,968
Ensembl chr 6:14,811,808...14,818,965

G

steroidogenic acute regulatory protein

increases expression

2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of STAR protein

NCBI chr16:66,267,094...66,274,368
Ensembl chr16:66,264,807...66,271,672

G

tachykinin, precursor 1

increases expression

2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of TAC1 mRNA

NCBI chr 4:35,679,183...35,687,180
Ensembl chr 4:35,679,704...35,687,178

G

transforming growth factor alpha

multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [TGFA protein results in increased phosphorylation of AKT1 protein]

NCBI chr 4:118,618,043...118,700,897
Ensembl chr 4:118,618,269...118,700,894

G

tumor necrosis factor

multiple interactions

[Lipopolysaccharides co-treated with 2,3-bis(4-hydroxyphenyl)-propionitrile] results in increased secretion of TNF protein
2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [Lipopolysaccharides results in increased secretion of TNF protein]
2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [Lipopolysaccharides results in increased expression of TNF protein]

PMID:21127968 PMID:30017638 PMID:30445053

NCBI chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629

G

tryptophan hydroxylase 2

multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [Estrogens deficiency results in decreased expression of TPH2 mRNA]

NCBI chr 7:50,685,694...50,789,424
Ensembl chr 7:50,685,694...50,789,424

G

transient receptor potential cation channel, subfamily V, member 1

multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [Capsaicin results in increased activity of TRPV1 protein]; Tamoxifen inhibits the reaction [2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [Capsaicin results in increased activity of TRPV1 protein]]

NCBI chr10:57,851,428...57,876,513
Ensembl chr10:57,851,428...57,876,513

G

ubiquinol cytochrome c reductase core protein 2

increases expression

2,3-bis(4-hydroxyphenyl)-propionitrile results in increased expression of UQCRC2 protein

NCBI chr 1:175,167,933...175,198,499
Ensembl chr 1:175,167,894...175,199,453

G

zinc finger (CCCH type), RNA binding motif and serine/arginine rich 2

multiple interactions

2,3-bis(4-hydroxyphenyl)-propionitrile inhibits the reaction [Estrogens deficiency results in decreased expression of ZRSR2 mRNA]

NCBI chr X:30,547,424...30,571,613
Ensembl chr X:30,547,536...30,570,125

Term paths to the root

Path 1
Term	Annotations
CHEBI ontology	19880
chemical entity	19878
group	19831
pseudohalo group	4581
cyano group	4581
nitrile	4581
2,3-bis(4-hydroxyphenyl)propionitrile	46
Path 2
Term	Annotations
CHEBI ontology	19880
subatomic particle	19878
composite particle	19878
hadron	19878
baryon	19878
nucleon	19878
atomic nucleus	19878
atom	19878
main group element atom	19817
p-block element atom	19817
carbon group element atom	19757
carbon atom	19754
organic molecular entity	19754
one-carbon compound	17869
hydrogen cyanide	4796
cyanides	4779
nitrile	4581
2,3-bis(4-hydroxyphenyl)propionitrile	46

paths to the root