| In ZINC since | Heavy atoms | Benign functionality |
|---|---|---|
| June 21st, 2008 | 20 | No |
Popular Name: Estradiol Estradiol
Find On: PubMed — Wikipedia — Google
CAS Numbers: 35380-71-3 , 50-28-2 , 53866-33-4 , 57-91-0 , 79037-37-9 , [50-28-2]
(17beta)-Estra-1,3,5(10)-triene-3,17-diol
(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol
(8xi,9xi,14xi,17alpha)-estra-1,3,5(10)-triene-3,17-diol
1,3,5-Estratriene-3,17beta-diol
17β-estra-1,3,5(10)-triene-3,17-diol
17¦Â-estradiol, oestradiol, 17¦Â-Oestradiol, ¦Â-Estradiol
35380-71-3; D07918; Estradiol hemihydrate; Estrasorb (TN); Vagifem (TN)
50-28-2; C00951; Estradiol; Estradiol-17beta; beta-Estradiol
50-28-2; CPD-352; beta-Estradiol; estradiol; estradiol-17beta
50-28-2; Estradiol-17 beta; Prestwick_207
beta-Estradiol, 99% (dry wt.), ca 3% water
Beta-estradiol; 17beta-Estradiol; 17b-Oestradiol; 3,17b-Dihydroxyestra-1,3,5(10)-triene
BETA-ESTRADIOL; CPD000059126; SAM001247032
BETA-ESTRADIOL; CPD000059126; SAM001247032; estradiol
CHEBI:23963; CHEBI:42475; CHEBI:4864; CHEBI:14219
CHLORDIAZEPOXIDE; ESTROGENS, ESTERIFIED; LS-187899; MENRIUM 5-2
CPD000059126; BETA-ESTRADIOL; 50-28-2
estra-1,3,5(10)-triene-3,17beta-diol
Estradiol Hemihydrate (FDA); Estradiol (BAN
| Type pH range | xlogP | Des A‑Pol Apolar desolvation (kcal/mol) | Des Pol Polar desolvation (kcal/mol) | H Don H-bond donors | H Acc H-bond acceptors | Chg Net charge | tPSA (Ų) | MWT Molecular weight (g/mol) | RB Rotatable bonds | DL |
|---|---|---|---|---|---|---|---|---|---|---|
| Ref Reference (pH 7) | 3.43 | 4.8 | -5.19 | 2 | 2 | 0 | 40 | 272.388 | 0 | ↓ |
| Note Type | Comments | Provided By |
|---|---|---|
| biological_source | Isol. from ovaries and pregnancy urine. Sex pheromone for mallard ducks | ZereneX Building Blocks |
| mechanism | . | ZereneX Building Blocks |
| Melting_Point | 175-178? | Alfa-Aesar |
| Melting_Point | 175-178° | Alfa-Aesar |
| MP | 176 | TCI |
| Mp [°C] | 176 - 180 | Acros Organics |
| ALOGPS_SOLUBILITY | 2.13e-02 g/l | DrugBank-approved |
| purity | 9.500000000000000e+001 | Enamine Building Blocks Enamine Building Blocks |
| Purity | 97% | Fluorochem |
| Purity | 99% | APIChem |
| UniProt Database Links | AB2C_ARATH; AB5C_ARATH; ABCA8_HUMAN; ABCCB_HUMAN; ALDO1_ARATH; ALDO2_ARATH; AMPN_HUMAN; AOXA_HUMAN; APOB_CHICK; CCD80_RAT; CETP_CHICK; CLC2G_MOUSE; COLI_SHEEP; CP191_CARAU; CP191_PIG; CP192_CARAU; CP192_PIG; CP193_PIG; CP19A_ANGJA; CP19A_BOVIN; CP19A_CALJ | ChEBI |
| UniProt Database Links | AB2C_ARATH; ABCA8_HUMAN; ABCCB_HUMAN; ALDO1_ARATH; ALDO2_ARATH; AMPN_HUMAN; AOXA_HUMAN; APOB_CHICK; CCD80_RAT; CETP_CHICK; CLC2G_MOUSE; COLI_SHEEP; CP191_CARAU; CP191_PIG; CP192_CARAU; CP192_PIG; CP193_PIG; CP19A_ANGJA; CP19A_BOVIN; CP19A_CALJA; CP19A_CAN | ChEBI |
| Patent Database Links | EP0902025; EP0970695; EP1281710; EP1782814; EP1862167; US2004167106; US2004235712; US2005054656; US2007202147; US2007259890; US2008292608; WO2005000404; WO2005116000 | ChEBI |
| Patent Database Links | EP1438962; EP1522306; EP1524269; EP1535618; EP1547600; EP1570848; EP1598081; EP1640009; EP1671624; EP1685843; EP1698329; EP1715038; EP1731142; EP1759734; EP1795185; EP1808160; EP1810665; EP1820494; EP1829529; EP1834959; EP1867321; EP1872774; EP1878438; EP | ChEBI |
| biological_use | Estradiol (and its semisynthetic esters) are used in estrogen replacement therapy | IBScreen Bioactives |
| mechanism | Estradiol enters cells freely and interacts with a cytoplasmic target cell receptor. | IBScreen Bioactives |
| Therapy | estrogen | SMDC Pharmakon |
| Target | Estrogen/progestogen Receptor | Selleck Chemicals |
| H phrase | H350: May cause cancer | Acros Organics |
| H phrase | H350: May cause cancer; H373: May cause damage to organs through prolonged or repeated exposure; H361fd: Suspected of damaging fertility. Suspected of damaging the unborn child; H362: May cause harm to breast-fed children | Acros Organics |
| PUBCHEM_SUBSTANCE_COMMENT | NCC_SAMPLE_SUPPLIER : Tocris Cookson Ltd.; NCC_SUPPLIER_STRUCTURE_ID : 101474 | NIH Clinical Collection via PubChem |
| Therapy | Nuclear receptor ligands: estrogen | SMDC Iconix |
| Target | Others | Selleck Chemicals |
| P phrase | P201: Obtain special instructions before use | Acros Organics |
| P phrase | P201: Obtain special instructions before use; P202: Do not handle until all safety precautions have been read and understood; P281: Use personal protective equipment as required; P308 + P313: IF exposed or concerned: Get medical advice/attention; P260: Do | Acros Organics |
| R phrase | R45: May cause cancer. | Acros Organics |
| R phrase | R45: May cause cancer.; R48/20/21/22: Harmful : danger of serious damage to health by prolonged exposure through inhalation, in contact with skin and if swallowed.; R62: Possible risk of impaired fertility.; R63: Possible risk of harm to the unborn child. | Acros Organics |
| Reactome Database Links | REACT_13668; REACT_25243; REACT_6949; REACT_9963 | ChEBI |
| S phrase | S53: Avoid exposure - obtain special instructions before use. | Acros Organics |
| S phrase | S53: Avoid exposure - obtain special instructions before use.; S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). | Acros Organics |
| PUBCHEM_SUBSTANCE_COMMENT | SAMPLE_SUPPLIER: Tocris Bioscience; SUPPLIER_STRUCTURE_ID: 101474 | NIH Clinical Collection via PubChem |
| Hazard | T: Toxic | Acros Organics |
| biological_use | The most potent of the natural estrogens | IBScreen Bioactives IBScreen Bioactives |
| mechanism | The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell. | IBScreen Bioactives |
| mechanism | When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. | IBScreen Bioactives |
| Code | Description | Organism Class | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| ANDR-1-E | Androgen Receptor (cluster #1 Of 4), Eukaryotic | Eukaryotes | 26 | 0.53 | Binding ≤ 10μM |
| ERR1-1-E | Estrogen-related Receptor Alpha (cluster #1 Of 1), Eukaryotic | Eukaryotes | 4 | 0.59 | Binding ≤ 10μM |
| ERR2-1-E | Estrogen-related Receptor Beta (cluster #1 Of 1), Eukaryotic | Eukaryotes | 3 | 0.60 | Binding ≤ 10μM |
| ESR1-1-E | Estrogen Receptor Alpha (cluster #1 Of 5), Eukaryotic | Eukaryotes | 0 | 0.00 | Binding ≤ 10μM |
| ESR2-1-E | Estrogen Receptor Beta (cluster #1 Of 4), Eukaryotic | Eukaryotes | 4 | 0.59 | Binding ≤ 10μM |
| GPER-1-E | G-protein Coupled Estrogen Receptor 1 (cluster #1 Of 1), Eukaryotic | Eukaryotes | 6 | 0.58 | Binding ≤ 10μM |
| SHBG-1-E | Testis-specific Androgen-binding Protein (cluster #1 Of 1), Eukaryotic | Eukaryotes | 50 | 0.51 | Binding ≤ 10μM |
| ERR1-1-E | Estrogen-related Receptor Alpha (cluster #1 Of 1), Eukaryotic | Eukaryotes | 6 | 0.58 | Functional ≤ 10μM |
| ERR2-1-E | Estrogen-related Receptor Beta (cluster #1 Of 1), Eukaryotic | Eukaryotes | 5 | 0.58 | Functional ≤ 10μM |
| ESR1-1-E | Estrogen Receptor Alpha (cluster #1 Of 3), Eukaryotic | Eukaryotes | 50 | 0.51 | Functional ≤ 10μM |
| ESR2-1-E | Estrogen Receptor Beta (cluster #1 Of 2), Eukaryotic | Eukaryotes | 10 | 0.56 | Functional ≤ 10μM |
| GPER-1-E | G-protein Coupled Estrogen Receptor 1 (cluster #1 Of 1), Eukaryotic | Eukaryotes | 0 | 0.00 | Functional ≤ 10μM |
| ADO-2-E | Aldehyde Oxidase (cluster #2 Of 3), Eukaryotic | Eukaryotes | 3000 | 0.39 | ADME/T ≤ 10μM |
| Z80224-1-O | MCF7 (Breast Carcinoma Cells) (cluster #1 Of 14), Other | Other | 1 | 0.63 | Functional ≤ 10μM |
| Z80226-1-O | MCF7-2A (cluster #1 Of 1), Other | Other | 0 | 0.00 | Functional ≤ 10μM |
| Z80475-2-O | SK-BR-3 (Breast Adenocarcinoma) (cluster #2 Of 3), Other | Other | 0 | 0.00 | Functional ≤ 10μM |
| Z81068-1-O | Ishikawa (Uterine Carcinoma Cells) (cluster #1 Of 1), Other | Other | 0 | 0.00 | Functional ≤ 10μM |
| Z81247-2-O | HeLa (Cervical Adenocarcinoma Cells) (cluster #2 Of 9), Other | Other | 1 | 0.63 | Functional ≤ 10μM |
| Uniprot | Swissprot | Description | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| ANDR_HUMAN | P10275 | Androgen Receptor, Human | 19.1 | 0.54 | Binding ≤ 1μM |
| ESR1_RAT | P06211 | Estrogen Receptor Alpha, Rat | 0.354 | 0.66 | Binding ≤ 1μM |
| ESR1_HUMAN | P03372 | Estrogen Receptor Alpha, Human | 0.1 | 0.70 | Binding ≤ 1μM |
| ESR1_BOVIN | P49884 | Estrogen Receptor Alpha, Bovin | 0.1 | 0.70 | Binding ≤ 1μM |
| ESR1_MOUSE | P19785 | Estrogen Receptor Alpha, Mouse | 2.2 | 0.61 | Binding ≤ 1μM |
| ESR2_MOUSE | O08537 | Estrogen Receptor Beta, Mouse | 0.5 | 0.65 | Binding ≤ 1μM |
| ESR2_HUMAN | Q92731 | Estrogen Receptor Beta, Human | 0.1 | 0.70 | Binding ≤ 1μM |
| ESR2_RAT | Q62986 | Estrogen Receptor Beta, Rat | 0.354 | 0.66 | Binding ≤ 1μM |
| ERR1_HUMAN | P11474 | Estrogen-related Receptor Alpha, Human | 3.6 | 0.59 | Binding ≤ 1μM |
| ERR2_HUMAN | O95718 | Estrogen-related Receptor Beta, Human | 3.2 | 0.59 | Binding ≤ 1μM |
| GPER_HUMAN | Q99527 | G-protein Coupled Estrogen Receptor 1, Human | 5.7 | 0.58 | Binding ≤ 1μM |
| SHBG_HUMAN | P04278 | Testis-specific Androgen-binding Protein, Human | 50 | 0.51 | Binding ≤ 1μM |
| ANDR_HUMAN | P10275 | Androgen Receptor, Human | 19.1 | 0.54 | Binding ≤ 10μM |
| ESR1_RAT | P06211 | Estrogen Receptor Alpha, Rat | 0.354 | 0.66 | Binding ≤ 10μM |
| ESR1_HUMAN | P03372 | Estrogen Receptor Alpha, Human | 0.1 | 0.70 | Binding ≤ 10μM |
| ESR1_BOVIN | P49884 | Estrogen Receptor Alpha, Bovin | 0.1 | 0.70 | Binding ≤ 10μM |
| ESR1_MOUSE | P19785 | Estrogen Receptor Alpha, Mouse | 2.2 | 0.61 | Binding ≤ 10μM |
| ESR2_MOUSE | O08537 | Estrogen Receptor Beta, Mouse | 0.5 | 0.65 | Binding ≤ 10μM |
| ESR2_HUMAN | Q92731 | Estrogen Receptor Beta, Human | 0.1 | 0.70 | Binding ≤ 10μM |
| ESR2_RAT | Q62986 | Estrogen Receptor Beta, Rat | 0.354 | 0.66 | Binding ≤ 10μM |
| ERR1_HUMAN | P11474 | Estrogen-related Receptor Alpha, Human | 3.6 | 0.59 | Binding ≤ 10μM |
| ERR2_HUMAN | O95718 | Estrogen-related Receptor Beta, Human | 3.2 | 0.59 | Binding ≤ 10μM |
| GPER_HUMAN | Q99527 | G-protein Coupled Estrogen Receptor 1, Human | 5.7 | 0.58 | Binding ≤ 10μM |
| SHBG_HUMAN | P04278 | Testis-specific Androgen-binding Protein, Human | 50 | 0.51 | Binding ≤ 10μM |
| ESR1_HUMAN | P03372 | Estrogen Receptor Alpha, Human | 0.1 | 0.70 | Functional ≤ 10μM |
| ESR2_HUMAN | Q92731 | Estrogen Receptor Beta, Human | 0.1 | 0.70 | Functional ≤ 10μM |
| ESR2_RAT | Q62986 | Estrogen Receptor Beta, Rat | 0.14 | 0.69 | Functional ≤ 10μM |
| ERR1_HUMAN | P11474 | Estrogen-related Receptor Alpha, Human | 5.9 | 0.58 | Functional ≤ 10μM |
| ERR2_HUMAN | O95718 | Estrogen-related Receptor Beta, Human | 4.6 | 0.58 | Functional ≤ 10μM |
| GPER_HUMAN | Q99527 | G-protein Coupled Estrogen Receptor 1, Human | 0.3 | 0.67 | Functional ≤ 10μM |
| Z81247 | Z81247 | HeLa (Cervical Adenocarcinoma Cells) | 0.59 | 0.65 | Functional ≤ 10μM |
| Z81068 | Z81068 | Ishikawa (Uterine Carcinoma Cells) | 0.1 | 0.70 | Functional ≤ 10μM |
| Z80224 | Z80224 | MCF7 (Breast Carcinoma Cells) | 0.1 | 0.70 | Functional ≤ 10μM |
| Z80226 | Z80226 | MCF7-2A | 0.1 | 0.70 | Functional ≤ 10μM |
| Z80475 | Z80475 | SK-BR-3 (Breast Adenocarcinoma) | 0.1 | 0.70 | Functional ≤ 10μM |
| ADO_RAT | Q9Z0U5 | Aldehyde Oxidase, Rat | 3000 | 0.39 | ADME/T ≤ 10μM |
| ADO_HUMAN | Q06278 | Aldehyde Oxidase, Human | 80 | 0.50 | ADME/T ≤ 10μM |
| Description | Species |
|---|---|
| Cytosolic sulfonation of small molecules | |
| Endogenous sterols | |
| Estrogen biosynthesis |
| Description | Species |
|---|---|
| G alpha (i) signalling events | |
| Nuclear Receptor transcription pathway | |
| Nuclear signaling by ERBB4 | |
| Peptide ligand-binding receptors | |
| PPARA activates gene expression | |
| Transcriptional activation of mitochondrial biogenesis | |
| Vitamins B6 activation to pyridoxal phosphate |
No pre-computed analogs available. Try a structural similarity search.