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Beta-anhydroepidigitoxigenin
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpene Lactone
| Canonical Smiles | O[C@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2(C1=CC[C@@H]2C1=CC(=O)OC1)C)C |
|---|---|
| InChI | InChI=1S/C23H32O3/c1-22-9-7-16(24)12-15(22)3-4-17-19-6-5-18(14-11-21(25)26-13-14)23(19,2)10-8-20(17)22/h6,11,15-18,20,24H,3-5,7-10,12-13H2,1-2H3/t15-,16-,17-,18+,20-,22-,23+/m0/s1 |
| InChIKey | FXWZKNUSMJAEKJ-LZELGGJRSA-N |
| Formula | C23H32O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 356.51 |
| Rotatable Bonds | 1 |
| TPSA | 46.53 |
| LogP | 4.41 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.78 |
| Exact Mass | 356.24 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Calotropis procera | Apocynaceae | Plantae | 141467 |
Showing of synonyms
Beta-anhydroepidigitoxigenin
Anhydroepidigitoxigenin
3-[(3S,5S,8R,9S,10S,13R,17S)-3-Hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
3-((3S,5S,8R,9S,10S,13R,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-17-yl)-2H-furan-5-one
??-Anhydrouzarigenin
SCHEMBL21578273
AKOS040762530
FS-9738
- Shaker KM, Morsy N, et al. (2010). Secondary metabolites from Calotropis procera (Aiton). Phytochemistry Letters,2010,3(4),212-216. [View]
No compound-protein relationship available.
SMILES: C1OC(=O)C=C1C(CC2)C(C=23)CCC4C3CCC5C4CCCC5
Level: 1
Mol. Weight: 356.51 g/mol
SMILES: C1CCC(C=12)CCC3C2CCC4C3CCCC4
Level: 0
Mol. Weight: 356.51 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 356.51 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.84
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.74
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.71
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.53
- Plasma Protein Binding
- 62.82
- 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
- Non-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
- 10.33
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.1
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.71
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.31
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Toxic
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -9.62
- Rat (Acute)
- 2.36
- Rat (Chronic Oral)
- 1.58
- Fathead Minnow
- 3.92
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 441.82
- Hydration Free Energy
- -2.95
- Log(D) at pH=7.4
- 3.88
- Log(P)
- 3.77
- Log S
- -5.49
- Log(Vapor Pressure)
- -7.57
- Melting Point
- 201.29
- pKa Acid
- 10.68
- pKa Basic
- 6.98
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9500 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9500 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9412 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9412 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.9407 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.9407 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9256 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9256 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9217 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9217 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9060 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9060 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8962 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8962 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8768 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8768 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8657 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8657 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8650 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8650 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8566 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8566 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8555 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8555 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8506 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8506 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8417 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8417 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8316 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8316 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.8166 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.8166 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 4 | 0.8053 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 4 | 0.8053 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 4 | 0.7994 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 4 | 0.7994 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 4 | 0.7983 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 4 | 0.7983 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 3 | 0.7677 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 3 | 0.7677 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 3 | 0.7658 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 3 | 0.7658 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7615 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7615 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7583 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7583 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7473 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7473 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.7462 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.7462 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 4 | 0.7417 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 4 | 0.7417 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7345 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7345 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7314 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7314 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7298 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7298 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 4 | 0.7267 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 4 | 0.7267 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7232 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7232 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 4 | 0.7222 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 4 | 0.7222 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7207 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7207 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 3 | 0.7202 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 3 | 0.7202 |