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20-hydroxyecdysone
- Family: Plantae - Podocarpaceae
- Kingdom: Plantae
-
Class: Steroid
- Subclass: Sterol
| Canonical Smiles | O[C@H]1C[C@@]2(C)[C@@H](C[C@H]1O)C(=O)C=C1[C@@H]2CC[C@]2([C@@]1(O)CC[C@@H]2[C@]([C@@H](CCC(O)(C)C)O)(O)C)C |
|---|---|
| InChI | InChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1 |
| InChIKey | NKDFYOWSKOHCCO-YPVLXUMRSA-N |
| Formula | C27H44O7 |
| HBA | 7 |
| HBD | 6 |
| MW | 480.64 |
| Rotatable Bonds | 5 |
| TPSA | 138.45 |
| LogP | 1.85 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.89 |
| Exact Mass | 480.31 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Atriplex portulacoides | Chenopodiaceae | Plantae | 376799 |
| 2 | Sida spinosa | Malvaceae | Plantae | 108380 |
| 3 | Podocarpus gracilior | Podocarpaceae | Plantae | 165205 |
Showing of synonyms
20-hydroxyecdysone
5289-74-7
Crustecdysone
Beta-Ecdysone
Ekdisten
Ecdysten
Beta-ECDYSTERONE
Beta-Ecdisone
(2beta,3beta,5beta,22R)-2,3,14,20,22,25-hexahydroxycholest-7-en-6-one
(+)-Ecdysterone
BIO101
(+)-20-Hydroxyecdysone
.beta-Ecdysterone
20-Hydroxyecdyson
UNII-779A7KPL0Y
20 Hydroxyecdysone
779A7KPL0Y
CHEBI:16587
BIO-101
20-Hydroxy-a-ecdysone
20-HYDROXY-.ALPHA.-ECDYSONE
NSC 629484
NSC-629484
Bio 101
BRN 1917578
AI3-44727
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
DTXSID5040388
20-HYDROXYECDYSONE [MI]
20-HYDROXYECDYSONE [WHO-DD]
Cholest-7-en-6-one, 2,3,14,20,22,25-hexahydroxy-, (2.beta.,3.beta.,5.beta.,22R)-
2-beta,3-beta,14,20,22,25-Hexahydroxy-5-beta-cholet-7-en-6-one
2beta,3beta,14alpha,20,22R,25-hexahydroxy-5beta-cholest-7-en-6-one
2beta,3beta,14alpha,20R,22R,25-hexahydroxy-5beta-cholest-7-en-6-one
Cholest-7-en-6-one, 2,3,14,20,22,25-hexahydroxy-, (2beta,3beta,5beta,22R)-
(22R)-2beta,3beta,14alpha,20,22,25-hexahydroxy-5beta-cholest-7-en-6-one
5-beta-Cholest-7-en-6-one, 2-beta,3-beta,14,20,22,25-hexahydroxy-, (22R)-
Cholest-7-en-6-one, 2,3,14,20,22,25-hexahydroxy-, (2-beta,3-beta,5-beta,22R)-
B-Ecdysterone
Beta-Ecydisone
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-((2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl)-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta(a)phenanthren-6-one
20r-hydroxyecdysone
20-Hydroxy-I+--ecdysone
BIO-101 [WHO-DD]
DTXCID3020388
20-HYDROXY-ALPHA-ECDYSONE
3a,7,8-trihydroxy-9a,11a-dimethyl-1-(2,3,6-trihydroxy-6-methylheptan-2-yl)-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta(a)phenanthren-5-one
3A,7,8-TRIHYDROXY-9A,11A-DIMETHYL-1-(2,3,6-TRIHYDROXY-6-METHYLHEPTAN-2-YL)-1H,2H,3H,5AH,6H,7H,8H,9H,9BH,10H,11H-CYCLOPENTA[A]PHENANTHREN-5-ONE
2beta,3beta,14alpha,20beta,22alpha,25-Hexahydroxycholest-7-en-6-one
Cholest-7-en-6-one, 2,3,14,20,22,25-hexahydroxy-, (2-beta,3-beta,5-beta,22R)-(9CI)
528974-7
Ecdysterone
Isoinokosterone
Viticosterone
Commisterone
Crustecdyson
Ecdysteron
Hydroxyecdysone
THE-7
20-OH ecdysone
MFCD00036740
B-Ecdysone
CHEMBL224128
20E
20-E
(2b,3b,5b,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one
SMR000539832
Ecdystene
Sarconeos
20-Hydroxyedysone
?- Ecdysone
Crustecdysone (Standard)
2beta,3beta,14alpha,20beta,22,25-Hexahydroxy-7-cholesten-6-one
|A-ECDYSONE,2,3,14,20,22,25-HEXAHYDROXY-7-CHOLESTEN-6-ONE
Cholest-7-en-6-one, 2,3,14,20,22,25-hexahydroxy-, (2b,3b,5b,22R)-
SCHEMBL22086
MLS001164644
MLS002207226
BIO 101 [WHO-DD]
GTPL11987
HY-N6979R
NKDFYOWSKOHCCO-YPVLXUMRSA-N
GLXC-07082
HMS2230L09
HY-N6979
BDBM50326777
HB3718
LMST01010209
S2417
AKOS004120029
CCG-269554
FH10452
AC-19603
AC-34796
CS-0007134
NS00097285
20-Hydroxyecdysone, >=93% (HPLC), powder
Q423338
(2|A,3|A,5|A,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one
(2Beta,3beta,5beta)-2,3,14,20,22,25-hexahydroxycholest-7-en-6-one
2-beta,3-beta,14,20,22,25-Hexahydroxy-5-beta-cholet-7-en-6- one
(2alpha,3alpha,5alpha,22R)-2,3,14,20,22,25-hexahydroxycholest-7-en-6-one
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-((2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl)-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(1R,2R)-1,2,5-trihydroxy-1,5-dimethyl-hexyl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
2,3,14-Trihydroxy-10,13-dimethyl-17-(1,2,5-trihydroxy-1,5-dimethyl-hexyl)-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-6-one
- Darwish FM, Reinecke MG (2003). Ecdysteroids and other constituents from Sida spinosa L. Phytochemistry,2003,62(8),1179-1184. [View] [PubMed]
- Nejma AB, Nguir A, et al. (2015). New septanoside and 20-hydroxyecdysone septanoside derivative from Atriplex portulacoides roots with preliminary biological activities. Bioorganic and Medicinal Chemistry Letters,2015,25(8),1665-1670. [View] [PubMed]
- Faiella L, Temraz A, et al. (2012). Terpenoids from the leaves of Podocarpus gracilior. Phytochemistry Letters,2012,5(2),297-300. [View]
Pubchem:
5459840
Cas:
5289-74-7
Zinc:
ZINC000238809241
Chebi:
16587
Nmrshiftdb2:
60018792
Metabolights:
MTBLC16587
Chembl:
CHEMBL224128
Comptox:
DTXSID5040388
Drugbank:
DB16935
Pdb Ligand:
20E
Bindingdb:
50326777
Selleck:
20-hydroxyecdysone
CPRiL:
4128
SMILES: C1CCC(C12)CCC3C2=CC(=O)C4C3CCCC4
Level: 0
Mol. Weight: 480.64 g/mol
Antibacterial
Anticholinesterase
Antioxidant
Absorption
- Caco-2 (logPapp)
- -5.0
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.25
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.38
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.52
- Plasma Protein Binding
- 73.29
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 3.14
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.42
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.28
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.75
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -96.62
- Rat (Acute)
- 4.8
- Rat (Chronic Oral)
- 2.37
- Fathead Minnow
- 3.83
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 504.08
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 1.6
- Log(P)
- 1.26
- Log S
- -2.47
- Log(Vapor Pressure)
- -10.56
- Melting Point
- 194.98
- pKa Acid
- 6.81
- pKa Basic
- 6.23
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.9264 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.9264 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8528 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8528 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7739 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7739 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7727 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7727 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7701 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7701 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7629 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7629 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7588 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7588 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7561 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7561 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7337 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7337 |