Estrone

Details

• Internal ID: caf115e9-19d5-425b-8a22-df5dd515759a
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Estrane steroids > Estrogens and derivatives
• IUPAC Name: (8R,9S,13S,14S)-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• SMILES (Canonical): CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4)O
• SMILES (Isomeric): C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O
• InChI: InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1
• InChI Key: DNXHEGUUPJUMQT-CBZIJGRNSA-N
• Popularity: 21,039 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₂O₂
• Molecular Weight: 270.40 g/mol
• Exact Mass: 270.161979940 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.82
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 53-16-7
• folliculin
• OESTRONE
• Theelin
• Thelykinin
• Ketohydroxyestrin
• estrovarin
• Estrugenone
• Kestrone
• Estron
• Tokokin
• Aquacrine
• Disynformon
• Folliculine
• Follicunodis
• Glandubolin
• Hiestrone
• Hormestrin
• Oestroform
• Oestronum
• Oestroperos
• Destrone
• Femidyn
• Folipex
• Folisan
• Menagen
• Oestrin
• Kolpon
• Unden
• Estrone-A
• Ketohydroxyoestrin
• Cristallovar
• Endofolliculina
• Crinovaryl
• Crystogen
• Estrusol
• Folikrin
• Follestrine
• Follestrol
• Hormofollin
• Hormovarine
• Ketodestrin
• Menformon
• Mestronaq
• Ovifollin
• Perlatan
• Solliculin
• Thelestrin
• Thynestron
• Wynestron
• 3-Hydroxyestra-1,3,5(10)-trien-17-one
• Ketohydroxy-Estratriene
• Femestrone injection
• Folliculine benzoate
• Estrogenic Substance
• 1,3,5(10)-Estratrien-3-ol-17-one
• Ovex (tablets)
• estrol
• Estrona
• Estrona [Spanish]
• Fem-O-Gen
• Estronum [INN-Latin]
• Estrona [INN-Spanish]
• Estronum
• Unden (pharmaceutical)
• Estra-1,3,5(10)-trien-17-one, 3-hydroxy-
• E(sub 1)
• 3-Hydroxy-17-keto-estra-1,3,5-triene
• hydroxyestrones
• Folliculinum
• 3-Hydroxy-oestra-1,3,5(10)-trien-17-one
• Estrone [USAN:INN]
• 1,3,5(10)-Oestratrien-3-ol-17-one
• 3-Hydroxy-17-keto-oestra-1,3,5-triene
• delta-1,3,5-Estratrien-3beta-ol-17-one
• delta-1,3,5-Oestratrien-3beta-ol-17-one
• delta-1,3,5-estratrien-3-beta-ol-17-one
• 3-Hydroxyestra-1,3,5(10)-triene-17-one
• delta-1,3,5-oestratrien-3-beta-ol-17-one
• (+)-Estrone
• Estrone (E1)
• CCRIS 285
• (+/-)-Oestrone
• 3-Hydroxy-1,3,5(10)-estratrien-17-one
• Unden (pharmaceutical) (VAN)
• (+/-)-Estrone
• Aquest
• Estradiol metabolite e1
• Oestrone [Steroidal oestrogens]
• Estrone DL-form [MI]
• HSDB 3324
• Estrone, (+/-)-
• NATURAL ESTROGENIC SUBSTANCE-ESTRONE
• 1,3,5-Estratrien-3-ol-17-one
• NSC 9699
• (8R,9S,13S,14S)-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• 19973-76-3
• EINECS 200-164-5
• UNII-2DI9HA706A
• Estrone (TN)
• BRN 1915077
• 2DI9HA706A
• DTXSID4022367
• CHEBI:17263
• 3-hydroxy-estra-1,3,5(10)-trien-17-one
• NSC-9699
• WAY 164397
• Estrone (JAN/USP/INN)
• Estrone [USP:INN:BAN]
• CHEMBL1405
• UNII-X9XKA379T9
• Fermidyn
• Estrin
• MLS000028475
• DTXCID402367
• Femestrone inj.
• X9XKA379T9
• EC 200-164-5
• 3-08-00-01171 (Beilstein Handbook Reference)
• CMC_13458
• Estra-1,3,5(10)-trien-17-one, 3-hydroxy-, (+/-)-
• SMR000058338
• 3-hydroxyl-1,3,5(10)-estratien-17-one
• ESTRONE (MART.)
• ESTRONE [MART.]
• E0026
• ESTRONE (USP-RS)
• ESTRONE [USP-RS]
• E 9750
• (13S)-3-hydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one
• [2,4,6,7-3H]-E1
• ESTRONE (USP MONOGRAPH)
• ESTRONE [USP MONOGRAPH]
• NSC9699
• (9beta,13alpha)-3-Hydroxyestra-1,3,5(10)-Trien-17-One
• Unigen
• Wehgen
• Follidrin (tablets)
• Ketophydroxyestrin
• WynestronPencap M
• (8R,9S,13S,14S)-3-HYDROXY-13-METHYL-6,7,8,9,11,12,13,14,15,16-DECAHYDRO-17H-CYCLOPENTA(A)PHENANTHREN-17-ONE
• (8R,9S,13S,14S)-3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthren-17-one
• ETHINYLESTRADIOL IMPURITY C (EP IMPURITY)
• ETHINYLESTRADIOL IMPURITY C [EP IMPURITY]
• Estrone, (+-)-Isomer
• ESTRADIOL HEMIHYDRATE IMPURITY A (EP IMPURITY)
• ESTRADIOL HEMIHYDRATE IMPURITY A [EP IMPURITY]
• Estrone, (9 beta)-Isomer
• oestron
• Estrone, (8 alpha)-Isomer
• 1,3,5-Oestratrien-3-ol-17-one
• estron-
• Oestrone, Estrone
• CAS-53-16-7
• NCGC00015423-03
• Therapeutic Estrone
• J3Z
• Hauck Brand of Estrone
• Hyrex Brand of Estrone
• ESTRONE [VANDF]
• Opera_ID_330
• ESTRONE [HSDB]
• Estrone, >=99%
• ESTRONE [INN]
• ESTRONE [JAN]
• ESTRONE [MI]
• Vortech Brand of Estrone
• Prestwick0_000914
• Prestwick1_000914
• Prestwick2_000914
• Prestwick3_000914
• Spectrum5_002047
• ESTRONE [WHO-DD]
• bmse000549
• D00ZFP
• FOLLICULINUM [HPUS]
• Lopac0_000513
• SCHEMBL21702
• BSPBio_000788
• MLS001077340
• MLS002695951
• MLS006011890
• BIDD:ER0145
• ESTRONE [ORANGE BOOK]
• SPBio_002977
• BPBio1_000868
• GTPL2818
• MEGxm0_000444
• SGCUT00128
• Estrone 1.0 mg/ml in Methanol
• ACon0_000083
• ACon1_000122
• BDBM17289
• [2,4,6,7-3H]-Estrone
• G03CA07
• G03CC04
• HMS1570H10
• HMS2090E22
• HMS2097H10
• HMS2232O15
• HMS3261H07
• HMS3714H10
• BCP13336
• HY-B0234
• to_000049
• Tox21_113567
• Tox21_201375
• Tox21_303651
• Tox21_500513
• BBL033470
• BL-090
• LMST02010004
• s1665
• STK801833
• AKOS005622512
• AKOS007930641
• Tox21_113567_1
• AC-1395
• CCG-204604
• DB00655
• DS-6316
• Estrone 100 microg/mL in Acetonitrile
• LP00513
• SDCCGSBI-0050497.P002
• SMP1_000123
• NCGC00023643-03
• NCGC00023643-04
• NCGC00023643-05
• NCGC00023643-06
• NCGC00023643-07
• NCGC00023643-08
• NCGC00023643-09
• NCGC00023643-10
• NCGC00023643-11
• NCGC00023643-12
• NCGC00023643-13
• NCGC00023643-15
• NCGC00023643-16
• NCGC00023643-22
• NCGC00179433-01
• NCGC00179433-02
• NCGC00179433-03
• NCGC00257402-01
• NCGC00258926-01
• NCGC00261198-01
• Estrone, meets USP testing specifications
• LS-64884
• D1,3,5(10)-Estratrien-3-ol-17-one
• 3-Hydroxyoestra-1,3,5(10)-trien-17-one
• AB00382990
• Estrone, VETRANAL(TM), analytical standard
• EU-0100513
• 3-hydroxy-estra-1,3,5(10)-triene-17-one
• C00468
• D00067
• EN300-120636
• AB00382990-16
• AB00382990-17
• AB00382990_18
• estra-1(10),2,4-trien-17-one, 3-hydroxy-
• Q414986
• SR-01000000085
• SR-01000075867
• Estra-1, 3,5 (10)-trien-17-ona, 3-hidroxi-
• Q-201073
• SR-01000000085-3
• SR-01000075867-1
• BRD-K81839095-001-04-6
• BRD-K81839095-001-30-1
• 86C77018-146D-4603-ACEA-CA0D8C4F1E2C
• Estrone, European Pharmacopoeia (EP) Reference Standard
• Z1530425070
• Estrone, United States Pharmacopeia (USP) Reference Standard
• Estrone, Pharmaceutical Secondary Standard; Certified Reference Material
• (1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadeca-2,4,6-trien-14-one
• (1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-14-one
• (8R,13S)-3-Hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7753	77.53%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7882	78.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9753	97.53%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.7750	77.50%
BSEP inhibitior	-	0.7221	72.21%
P-glycoprotein inhibitior	-	0.9167	91.67%
P-glycoprotein substrate	-	0.6988	69.88%
CYP3A4 substrate	+	0.6957	69.57%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	-	0.7000	70.00%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9353	93.53%
CYP2C19 inhibition	-	0.8954	89.54%
CYP2D6 inhibition	-	0.9599	95.99%
CYP1A2 inhibition	+	0.9017	90.17%
CYP2C8 inhibition	+	0.9412	94.12%
CYP inhibitory promiscuity	-	0.8681	86.81%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7600	76.00%
Carcinogenicity (trinary)	Non-required	0.3609	36.09%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9584	95.84%
Skin irritation	+	0.6660	66.60%
Skin corrosion	-	0.9023	90.23%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7459	74.59%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	+	0.9000	90.00%
skin sensitisation	-	0.9435	94.35%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8450	84.50%
Acute Oral Toxicity (c)	III	0.7811	78.11%
Estrogen receptor binding	+	0.9287	92.87%
Androgen receptor binding	+	0.8695	86.95%
Thyroid receptor binding	+	0.7772	77.72%
Glucocorticoid receptor binding	+	0.8971	89.71%
Aromatase binding	+	0.8686	86.86%
PPAR gamma	-	0.5378	53.78%
Honey bee toxicity	-	0.8981	89.81%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9907	99.07%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5393	Q9UNQ0	ATP-binding cassette sub-family G member 2	3000 nM	IC50	PMID: 12533678
CHEMBL1293237	P54132	Bloom syndrome protein	199.5 nM; 199.5 nM; 199.5 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED
CHEMBL2421	P08185	Corticosteroid binding globulin	10000 nM	Ki	PMID: 15139751
CHEMBL1978	P11511	Cytochrome P450 19A1	2500 nM	Ki	PMID: 26469743
CHEMBL3356	P05177	Cytochrome P450 1A2	1258.93 nM	AC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	1995.3 nM; 1995.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	6309.6 nM; 1.3 nM; 1.3 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED
CHEMBL3181	P14061	Estradiol 17-beta-dehydrogenase 1	109 nM; 330 nM; 109 nM; 218 nM; 810 nM; 600 nM	IC50; IC50; IC50; IC50; IC50; IC50	PMID: 19836949; PMID: 16480268; via Super-PRED; PMID: 18035543; PMID: 18372081; PMID: 18372081
CHEMBL206	P03372	Estrogen receptor alpha	7 nM; 29 nM; 7.647 nM; 96 nM	EC50; IC50; IC50; IC50	via Super-PRED; PMID: 16610787; via CMAUP; PMID: 19836949
CHEMBL242	Q92731	Estrogen receptor beta	8 nM; 540 nM; 31 nM	EC50; IC50; IC50	via Super-PRED; PMID: 15081034; PMID: 16610787
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	15848.9 nM; 15.8 nM; 15.8 nM; 15.8 nM; 15848.9 nM	Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED; via CMAUP; via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	3981.1 nM; 3981.1 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293298	Q01453	Peripheral myelin protein 22	2685.5 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	11.2 nM; 28183.8 nM; 11.2 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED
CHEMBL1833	P41595	Serotonin 2b (5-HT2b) receptor	13630 nM	IC50	via CMAUP
CHEMBL228	P31645	Serotonin transporter	5301 nM	IC50	via CMAUP
CHEMBL3305	P04278	Testis-specific androgen-binding protein	6.607 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.11%	91.11%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	97.84%	89.05%
CHEMBL2581	P07339	Cathepsin D	93.63%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.49%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.91%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.29%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.10%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.09%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.81%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.76%	97.25%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	88.03%	97.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.15%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.00%	90.71%
CHEMBL217	P14416	Dopamine D2 receptor	84.73%	95.62%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.01%	93.40%
CHEMBL1937	Q92769	Histone deacetylase 2	82.58%	94.75%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	82.41%	100.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.14%	85.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.19%	100.00%

Plants that contains it

• Aglaia elaeagnoidea
• Aristolochia littoralis
• Astragalus gummifer
• Cardiospermum halicacabum
• Centaurea nigrescens
• Cirsium japonicum
• Coreopsis fasciculata
• Crepis foetida
• Crinum viviparum
• Cuphea carthagenensis
• Dioscoreophyllum cumminsii
• Dorstenia lindeniana
• Erigeron canadensis
• Euphorbia segetalis
• Garcinia celebica
• Ozoroa insignis
• Parastrephia lepidophylla
• Penstemon secundiflorus
• Perilla frutescens
• Phaseolus vulgaris
• Phedimus kamtschaticus
• Phlogacanthus thyrsiformis
• Phoenix dactylifera
• Phytolacca acinosa
• Piper arboreum
• Pouzolzia occidentalis
• Psidium guajava
• Punica granatum
• Ruta microcarpa
• Selinum carvifolium
• Sidastrum multiflorum
• Solanum glaucophyllum
• Syncolostemon parviflorus
• Thuja plicata
• Triglochin maritima
• Urtica triangularis
• Zanthoxylum schreberi

Cross-Links

• PubChem: 5870
• NPASS: NPC190501
• ChEMBL: CHEMBL1405
• LOTUS: LTS0023699
• wikiData: Q414986