Dienestrol

Details

• Internal ID: 2875b997-4fa1-48fe-b326-49faf784662f
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 4-[(2E,4E)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
• SMILES (Canonical): CC=C(C1=CC=C(C=C1)O)C(=CC)C2=CC=C(C=C2)O
• SMILES (Isomeric): C/C=C(/C(=C/C)/C1=CC=C(C=C1)O)\C2=CC=C(C=C2)O
• InChI: InChI=1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3/b17-3+,18-4+
• InChI Key: NFDFQCUYFHCNBW-SCGPFSFSSA-N
• Popularity: 969 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈O₂
• Molecular Weight: 266.30 g/mol
• Exact Mass: 266.130679813 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.60
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• Dienoestrol
• Dehydrostilbestrol
• Cycladiene
• E,E-Dienestrol
• Restrol
• Dienol
• Estraguard
• Estroral
• Follidiene
• Oestrasid
• Oestrodiene
• Synestrol
• 13029-44-2
• 84-17-3
• Estragard
• Gynefollin
• Oestroral
• Dinovex
• Retalon
• (E,E)-Dienestrol
• Estrodienol
• Hormofemin
• Dehydrostilboestrol
• Oestrodienol
• Dienesterol
• Dinestrol
• Follormon
• Oestrovis
• Sexadien
• Teserene
• Willnestrol
• Agaldog
• alpha-Dienestrol
• para-Dien
• Dienestrol (E,E)
• Dienestrolo
• Dienestrolum
• Dienoestrol bp
• p,p'-(Diethylideneethylene)diphenol
• Di(p-oxyphenyl)-2,4-hexadiene
• Dienestrol [INN]
• 3,4-Bis(4-hydroxyphenyl)-2,4-hexadiene
• Dienestrolo [DCIT]
• 4,4'-(Diethylideneethylene)diphenol
• 4-[(2E,4E)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
• Dienestrolum [INN-Latin]
• Dienestrol, (E,E)-Isomer
• MLS000069528
• 3,4-Bis(p-hydroxyphenyl)-2,4-hexadiene
• 4,4'-hexa-2,4-diene-3,4-diyldiphenol
• Dienestrol, .alpha.-
• 4,4'-Hydroxy-gamma,delta-diphenyl-beta,delta-hexadiene
• Di(para-oxyphenyl)-2,4-hexadiene
• Dienestrol (USP/INN)
• NSC 59809
• UNII-RRW32X4U1F
• 4,4'-(1,2-Diethylidene-1,2-ethanediyl)bisphenol
• .alpha.-dienestrol diacetate
• RRW32X4U1F
• Isodienestrol
• Phenol, 4,4'-(diethylideneethylene)di-
• Dienestrol [USP:INN:BAN]
• DV (TN)
• para,para'-(Diethylideneethylene)diphenol
• SMR000058597
• 4,4'-((2E,4E)-hexa-2,4-diene-3,4-diyl)diphenol
• CCRIS 9121
• 3,4-Bis(para-hydroxyphenyl)-2,4-hexadiene
• Dienestrol diacetate, .alpha.-
• 2,4-Hexadiene, 3,4-bis(4-hydroxyphenyl)-
• HSDB 3313
• EINECS 201-519-7
• Dienoestrol [Nonsteroidal oestrogens]
• NSC-59809
• DV
• 4,4'-Dihydroxy-gamma,delta-diphenyl-beta,delta-hexadiene
• Phenol, 4,4'-(1,2-diethylidene-1,2-ethanediyl)bis-
• (E,E)-4,4'-(Diethylideneethylene)diphenol
• Phenol, 4,4'-(1,2-diethylidene-1,2-ethanediyl)bis-, (E,E)-
• 4,4'-(2E,4E)-hexa-2,4-diene-3,4-diyldiphenol
• DTXCID50809641
• Phenol, 4,4'-(diethylideneethylene)di-, trans-, (E,E)-
• Phenol, 4,4'-((1E,2E)-1,2-diethylidene-1,2-ethanediyl)bis-
• Phenol, 4,4'-[(1E,2E)-1,2-diethylidene-1,2-ethanediyl]bis-
• Dienestrol [USAN:INN]
• SR-01000003032
• CHEBI:4518
• DTXSID7022382
• dienestrol-
• CAS-84-17-3
• Prestwick_52
• NCGC00016335-01
• Restrol, Dienestrol
• Dienestrol trans-form
• DIENESTROL [MI]
• Opera_ID_421
• 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
• alpha-dienestrol diacetate
• Prestwick2_000798
• Prestwick3_000798
• Spectrum5_000875
• DIENESTROL [HSDB]
• DIENESTROL [VANDF]
• D09ZQN
• DIENESTROL [MART.]
• CHEMBL1018
• DIENESTROL [WHO-DD]
• SCHEMBL52170
• BSPBio_000936
• BSPBio_002177
• MLS001077274
• MLS002207222
• MLS002222156
• SPECTRUM1500241
• BPBio1_001030
• cid_667476
• GTPL7160
• SCHEMBL2896853
• DIENESTROL [EP IMPURITY]
• DIENESTROL [ORANGE BOOK]
• BDBM40491
• HMS502G13
• DIENESTROL [USP IMPURITY]
• DTXSID20873495
• HMS1570O18
• HMS1920G04
• HMS2091M14
• HMS2097O18
• HMS2232M11
• HMS3714O18
• Pharmakon1600-01500241
• DIENESTROL TRANS-FORM [MI]
• HY-B1403
• Tox21_110378
• CCG-40189
• MFCD00050983
• NSC756734
• s1858
• AKOS015902490
• Tox21_110378_1
• 1ST2217
• CS-4911
• DB00890
• NSC-756734
• IDI1_000771
• NCGC00018153-03
• NCGC00018153-04
• NCGC00018153-05
• NCGC00018153-06
• NCGC00018153-07
• NCGC00018153-10
• NCGC00022210-03
• NCGC00022210-04
• NCGC00178779-01
• NCGC00178779-02
• AC-13162
• BS-17610
• SBI-0051344.P003
• LS-104381
• 4,4'-(Hexa-2,4-diene-3,4-diyl)diphenol
• D0449
• C08090
• D00898
• D81865
• Dienestrol, VETRANAL(TM), analytical standard
• AB00051967_16
• A936711
• EN300-24161605
• J-005782
• Q5274949
• SR-01000003032-2
• SR-01000003032-4
• 4,4'-[(2E,4E)-2,4-Hexadiene-3,4-diyl]diphenol
• BRD-K55106630-001-01-0
• BRD-K95309561-001-05-6
• BRD-K95309561-001-15-5
• Dienestrol, European Pharmacopoeia (EP) Reference Standard
• Dienestrol, United States Pharmacopeia (USP) Reference Standard
• 4,4'-Dihydroxy-.gamma.,.delta.-diphenyl-.beta.,.delta.-hexadiene
• Phenol, 4,4'-(1,2-diethylidene-1,2-ethanediyl)bis-, (E,E-(9CI)
• PHENOL, 4,4'-(1,2-DIETHYLIDENE-1,2-ETHANEDIYL)BIS-, (E,E)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9974	99.74%
Caco-2	+	0.6415	64.15%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8033	80.33%
OATP2B1 inhibitior	-	0.7758	77.58%
OATP1B1 inhibitior	-	0.7737	77.37%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.5777	57.77%
P-glycoprotein inhibitior	-	0.9245	92.45%
P-glycoprotein substrate	-	0.9563	95.63%
CYP3A4 substrate	-	0.7479	74.79%
CYP2C9 substrate	-	0.7735	77.35%
CYP2D6 substrate	-	0.7087	70.87%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	+	0.8605	86.05%
CYP2C19 inhibition	+	0.8993	89.93%
CYP2D6 inhibition	-	0.8201	82.01%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.4661	46.61%
CYP inhibitory promiscuity	+	0.8844	88.44%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.5493	54.93%
Carcinogenicity (trinary)	Non-required	0.4556	45.56%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.8540	85.40%
Skin irritation	-	0.8150	81.50%
Skin corrosion	-	0.9313	93.13%
Ames mutagenesis	-	0.9900	99.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5181	51.81%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	+	0.9289	92.89%
Respiratory toxicity	-	0.9333	93.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	+	0.6402	64.02%
Acute Oral Toxicity (c)	III	0.8176	81.76%
Estrogen receptor binding	+	0.9280	92.80%
Androgen receptor binding	+	0.9319	93.19%
Thyroid receptor binding	+	0.7724	77.24%
Glucocorticoid receptor binding	+	0.9079	90.79%
Aromatase binding	+	0.8743	87.43%
PPAR gamma	+	0.8970	89.70%
Honey bee toxicity	-	0.9779	97.79%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9782	97.82%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	25118.9 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	25118.9 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	19952.6 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	7943.3 nM; 7943.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL206	P03372	Estrogen receptor alpha	13241.54 nM	EC50	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	28183.8 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	8912.5 nM; 31622.8 nM; 19952.6 nM; 25118.9 nM; 10000 nM	Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	1995.3 nM; 10 nM	Potency; Potency	via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL242	Q92731	Estrogen receptor beta	95.94%	98.35%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	89.01%	93.10%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.03%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	85.55%	91.49%
CHEMBL2581	P07339	Cathepsin D	83.94%	98.95%
CHEMBL4208	P20618	Proteasome component C5	83.90%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.81%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.55%	91.11%

Plants that contains it

• Magnolia obovata
• Magnolia officinalis

Cross-Links

• PubChem: 667476
• NPASS: NPC26244
• ChEMBL: CHEMBL1018
• LOTUS: LTS0090685
• wikiData: Q5274949