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Ponasterone A
- Family: Plantae - Podocarpaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Ecdysone
| Canonical Smiles | CC(CC[C@H]([C@@]([C@H]1CC[C@@]2([C@]1(C)CC[C@H]1C2=CC(=O)[C@H]2[C@]1(C)C[C@H](O)[C@@H](C2)O)O)(O)C)O)C |
|---|---|
| InChI | InChI=1S/C27H44O6/c1-15(2)6-7-23(31)26(5,32)22-9-11-27(33)17-12-19(28)18-13-20(29)21(30)14-24(18,3)16(17)8-10-25(22,27)4/h12,15-16,18,20-23,29-33H,6-11,13-14H2,1-5H3/t16-,18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1 |
| InChIKey | PJYYBCXMCWDUAZ-JJJZTNILSA-N |
| Formula | C27H44O6 |
| HBA | 6 |
| HBD | 5 |
| MW | 464.64 |
| Rotatable Bonds | 5 |
| TPSA | 118.22 |
| LogP | 2.74 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.89 |
| Exact Mass | 464.31 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Podocarpus gracilior | Podocarpaceae | Plantae | 165205 |
Showing of synonyms
Ponasterone A
13408-56-5
25-deoxyecdysterone
25-Deoxycedysterone
2,3,14,20,22-PENTAHYDROXYCHOLEST-7-EN-6-ONE
UNII-84986BG3NG
CHEBI:28135
84986BG3NG
(2S,3R,5R,9R,10R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
PONASTERONE A [MI]
DTXSID0040595
2beta,3beta,14,20,22-Pentahydroxy-5beta-cholest-7-en-6-one
(22R)-2beta,3beta,14,20,22-pentahydroxy-5beta-cholest-7-en-6-one
Cholest-7-en-6-one, 2,3,14,20,22-pentahydroxy-, (2.beta.,3.beta.,5.beta.,22R)-
Cholest-7-en-6-one, 2,3,14,20,22-pentahydroxy-, (2beta,3beta,5beta,22R)-
AI3-44686
(2beta,3beta,5beta,22R)-2,3,14,20,22-pentahydroxycholest-7-en-6-one
5.BETA.-CHOLEST-7-EN-6-ONE, 2.BETA.,3.BETA.,14,20,22-PENTAHYDROXY-, (22R)-
25-deoxy-20-ecdysone
25d20E
(2S,3R,5R,9R,10R,13R,14S,17S)-17-((2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl)-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta(a)phenanthren-6-one
DTXCID8020595
2 beta,3 beta,14,20,22-Pentahydroxy-5 beta-cholest-7-en-6-one
(2I2,3I2,5I2,22R)-2,3,14,20,22-Pentahydroxycholest-7-en-6-one
5BETA-CHOLEST-7-EN-6-ONE, 2BETA,3BETA,14,20,22-PENTAHYDROXY-, (22R)-
CHEMBL549789
P1A
25-Deoxy-20-hydroxyecdysone
Ponasteron a
(2ss,3ss,5ss,22R)-2,3,14,20,22-Pentahydroxycholest-7-en-6-one
(22R)-2ss,3ss,14,20,22-Pentahydroxy-5ss-cholest-7-en-6-one
Ponasterone A, >=65%
SCHEMBL61749
GLXC-10978
HY-N1534
BDBM50326776
HB4033
LMST01010195
MFCD00272144
AKOS032948506
NCGC00390385-01
DA-77002
FP158558
CS-0017083
C08835
E71095
Q27103520
(2alpha,3alpha,5alpha,22R)-2,3,14,20,22-pentahydroxycholest-7-en-6-one
2beta,3beta,14alpha,20R,22R-Pentahydroxy-5beta-cholest-7-en-6-one
25-DEOXY-20-HYDROXYECDYSONE,
- Faiella L, Temraz A, et al. (2012). Terpenoids from the leaves of Podocarpus gracilior. Phytochemistry Letters,2012,5(2),297-300. [View]
Pubchem:
115127
Cas:
13408-56-5
Zinc:
ZINC000004097822
Kegg Ligand:
C08835
Chebi:
28135
Nmrshiftdb2:
60146128
Chembl:
CHEMBL549789
Comptox:
DTXSID0040595
Pdb Ligand:
P1A
Bindingdb:
50326776
CPRiL:
124443
SMILES: C1CCC(C12)CCC3C2=CC(=O)C4C3CCCC4
Level: 0
Mol. Weight: 464.64 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.72
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.01
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.73
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.7
- Plasma Protein Binding
- 78.91
- 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
- 4.27
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.69
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.26
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.03
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- 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
- -75.9
- Rat (Acute)
- 4.42
- Rat (Chronic Oral)
- 2.36
- Fathead Minnow
- 3.82
- 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
- 484.0
- Hydration Free Energy
- -3.07
- Log(D) at pH=7.4
- 3.19
- Log(P)
- 2.6
- Log S
- -3.2
- Log(Vapor Pressure)
- -9.98
- Melting Point
- 180.34
- pKa Acid
- 7.12
- pKa Basic
- 6.18
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8604 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8604 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8054 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8054 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7731 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7731 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 4 | 0.7671 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 4 | 0.7671 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7556 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.7556 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7508 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7508 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7370 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7370 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 4 | 0.7299 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 4 | 0.7299 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.7275 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.7275 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7113 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7113 |