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Alpha-estradiol
- Family: Plantae - Rosaceae
- Kingdom: Plantae
-
Class: Steroid
- Subclass: Phytosterol
| Canonical Smiles | Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@H]2O)C |
|---|---|
| InChI | InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1 |
| InChIKey | VOXZDWNPVJITMN-SFFUCWETSA-N |
| Formula | C18H24O2 |
| HBA | 2 |
| HBD | 2 |
| MW | 272.39 |
| Rotatable Bonds | 0 |
| TPSA | 40.46 |
| LogP | 3.61 |
| Number Rings | 4 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.67 |
| Exact Mass | 272.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Prunus armeniaca | Rosaceae | Plantae | 36596 |
Showing of synonyms
Alpha-estradiol
17alpha-Estradiol
57-91-0
Alfatradiol
17a-estradiol
17-alpha-Estradiol
3,17-Dihydroxyestratriene
Estradiol-17alpha
Epiestrol
A-Estradiol
17.alpha.-Estradiol
17-Epiestradiol
.alpha.-Estradiol
Alfatradiol [INN]
Estra-1,3,5(10)-triene-3,17alpha-diol
(8R,9S,13S,14S,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
Oestradiol-17alpha
Oestradiol-17-alpha
Estradiol, .alpha.-
NSC 20293
Estradiol 17-.alpha.
ESTRADIOL, ALPHA-
17a-Oestradiol
17-epi-Estradiol
Alfatradiol (INN)
CCRIS 7203
17alpha-E2
DTXSID8022377
CHEBI:17160
3VQ38D63M7
EINECS 200-354-8
1,3,5-Estratriene-3,17-alpha-diol
(17alpha)-estra-1,3,5(10)-triene-3,17-diol
ALFATRADIOL [MART.]
BRN 2698044
DTXCID702377
Oestra-1,3,5(10)-triene-3,17alpha-diol
.ALPHA.-ESTRADIOL [MI]
MITO-4509
3,17alpha-Dihydroxyestra-1,3,5(10)-triene
3,17alpha-Dihydroxyoestra-1,3,5(10)-triene
Estra-1,3,5(10)-triene-3,17.alpha.-diol
17A-ESTRADIOL [WHO-DD]
1,3,5-Estratriene-3,17a-diol
3,17-alpha-Dihydroxyoestra-1,3,5(10)-triene
4-06-00-06611 (Beilstein Handbook Reference)
Estra-1,3,5(10)-triene-3,17a-diol
Oestra-1,3,5(10)-triene-3,17a-diol
3,17a-Dihydroxyestra-1,3,5(10)-triene
3,17a-Dihydroxyoestra-1,3,5(10)-triene
ALFATRADIOL (MART.)
13b-Methyl-1,3,5(10)-gonatriene-3,17a-diol
ETHINYLESTRADIOL IMPURITY L [EP IMPURITY]
ESTRADIOL HEMIHYDRATE IMPURITY B [EP IMPURITY]
Estra-1,3,5(10)-triene-3,17-diol, (17-alpha)-
ETHINYLESTRADIOL IMPURITY L (EP IMPURITY)
ESTRADIOL HEMIHYDRATE IMPURITY B (EP IMPURITY)
Alfatradiolum
(1S,10R,11S,14R,15S)-15-methyltetracyclo(8.7.0.02,7.011,15)heptadeca-2(7),3,5-triene-5,14-diol
(1S,10R,11S,14R,15S)-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-triene-5,14-diol
(8R,9S,13S,14S,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta(a)phenanthrene-3,17-diol
17alpha-Oestradiol
ESTRADIOL 17-ALPHA
1,3,5-Estratriene-3,17alpha-diol
Estra-1,3,5(10)trien-3,17alpha-diol
13beta-methyl-1,3,5(10)-gonatriene-3,17alpha-diol
200-354-8
Epiestradiol
17|A-estradiol
17alpha estradiol
17?-Estradiol
17.alpha.-Oestradiol
Oestradiol-17.alpha.
Estradiol, 17.alpha.-
(8R,9S,13S,14S,17R)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
17-alpha-Estradiol 100 microg/mL in Acetonitrile
17 ?-Estradiol
MFCD00064144
MX-4509
CAS-57-91-0
Estra-1,3,5(10)-triene-3,17alpha-diol (17alpha-Estradiol
17-epi-Estradiol)
(1S,10R,11S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol
3,3,5(10)-triene
UNII-3VQ38D63M7
Alpha -Estradiol
1,3,5-Estratriene-3,17.alpha.-diol
I+/--Astradiol
Estra-1,3,5(10)-triene-3,17-diol, (17a)-
Alphaestradiol powder
Estradiol, 17alpha-
Oestra-1,3,5(10)-triene-3,17.alpha.-diol
3,17.alpha.-Dihydroxyestra-1,3,5(10)-triene
Alpha-Estradiol, 98%
3,17.alpha.-Dihydroxyoestra-1,3,5(10)-triene
UPCMLD-DP131
Alpha-Estradiol (Standard)
Ethinyl Estradiol Impurity L
KBioGR_002281
KBioSS_002282
BIDD:ER0163
SCHEMBL121568
CHEMBL286452
HY-B0141AR
UPCMLD-DP131:001
BDBM20624
GTPL12600
HY-B0141A
KBio2_002281
KBio2_004849
KBio2_007417
KBio3_002761
ABP-150
MSK2270
CMAP_000011
Tox21_201262
Tox21_303644
HB2493
LMST02010029
S5910
1,5-Estratriene-3,17.alpha.-diol
AKOS024457306
AC-2168
FE22820
GS-5672
NCGC00161666-01
NCGC00161666-02
NCGC00161666-03
NCGC00161666-04
NCGC00256569-01
NCGC00258814-01
Alpha-Estradiol, powder, >=98% (TLC)
1,3,5(10)-Estratriene-3,17alpha-diol
CS-0014231
E0919
Estra-1,5(10)-triene-3,17.alpha.-diol
NS00075580
Oestra-1,5(10)-triene-3,17.alpha.-diol
3,17alpha-Dihydroxy-1,3,5(10)-estratriene
C02537
D07121
H10403
Alpha-Estradiol, VETRANAL(TM), analytical standard
Q4721888
WLN: L E5 B666TTT&J E1 FQ OQ 17-ALPHA
13beta-methyl-1,3,5(10)-gonatrien-3,17alpha-diol
Estra-1,5(10)-triene-3,17-diol, (17.alpha.)-
23E54080-77C2-4457-A388-FCBCE0B68C38
17alpha-Estradiol (17-epi-Estradiol
Estra-1,3,5(10)-triene-3,17alpha-diol)
(17a)-Estra-1,3,5(10)-triene-3,17-diol
- Awad O. (1974). Steroidal estrogens of Prunus armeniaca seeds. Phytochemistry, 1974, 13(3), 678-679. [View]
Pubchem:
68570
Cas:
57-91-0
Gnps:
CCMSLIB00005774490
Zinc:
ZINC000003815415
Kegg Ligand:
C02537
Chebi:
17160
Metabolights:
MTBLC17160
Chembl:
CHEMBL286452
Comptox:
DTXSID8022377
Bindingdb:
20624
CPRiL:
16302
SMILES: C1CCC(C12)CCC3c4c(CCC23)cccc4
Level: 0
Mol. Weight: 272.39 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.94
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.330
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.88
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.760
- Plasma Protein Binding
- 81.09
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.600
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.220
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.350
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.890
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Toxic
- NR-ER-LBD
- Toxic
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- 0.840
- Rat (Acute)
- 2.210
- Rat (Chronic Oral)
- 2.120
- Fathead Minnow
- 3.920
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 374.700
- Hydration Free Energy
- -5.900
- Log(D) at pH=7.4
- 3.810
- Log(P)
- 3.66
- Log S
- -4.59
- Log(Vapor Pressure)
- -7.32
- Melting Point
- 207.14
- pKa Acid
- 11.54
- pKa Basic
- 7.37
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.9275 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9198 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.9074 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9025 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.8951 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8889 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8765 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 4 | 0.8764 |
| Steroid 17-alpha-hydroxylase/17,20 lyase | P05093 | CP17A_HUMAN | Homo sapiens | 3 | 0.8760 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.8671 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8621 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 4 | 0.8619 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 3 | 0.8619 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8601 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 3 | 0.8558 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8539 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8508 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.8493 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.8455 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8370 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8315 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.8270 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8247 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8201 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 3 | 0.8165 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.7949 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7942 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7913 |
| Sterol 14alpha-demethylase | P9WPP9 | CP51_MYCTU | Mycobacterium tuberculosis | 4 | 0.7844 |
| Sulfotransferase 1E1 | P49891 | ST1E1_MOUSE | Mus musculus | 4 | 0.7841 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7832 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7810 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.7802 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7781 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7768 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.7764 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7761 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.7759 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7735 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.7697 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7688 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7650 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.7642 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.7627 |
| Estrogen receptor beta | Q92731 | ESR2_HUMAN | Homo sapiens | 4 | 0.7623 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7608 |
| Estrogen receptor beta | Q92731 | ESR2_HUMAN | Homo sapiens | 4 | 0.7597 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7568 |
| Estrogen receptor beta | Q62986 | ESR2_RAT | Rattus norvegicus | 4 | 0.7547 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.7539 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.7535 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7534 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.7520 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 4 | 0.7520 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.7484 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 4 | 0.7457 |
| Estrogen receptor beta | Q92731 | ESR2_HUMAN | Homo sapiens | 4 | 0.7440 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7439 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7371 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7370 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7362 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7321 |
| cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B | Q13370 | PDE3B_HUMAN | Homo sapiens | 3 | 0.7317 |
| AGAP003309-PA | A0A1U7F4W2 | A0A1U7F4W2_ANOGA | Anopheles gambiae | 3 | 0.7299 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.7289 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7265 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 4 | 0.7260 |
| High affinity 3',5'-cyclic-AMP phosphodiesterase 7A | Q13946 | PDE7A_HUMAN | Homo sapiens | 3 | 0.7241 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7238 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.7229 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7216 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7138 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7109 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7101 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7082 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7040 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7040 |