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14beta-hydroxybufa-3,5,20,22-tetraenolide
- Family: Plantae - Hyacinthaceae
- Kingdom: Plantae
-
Class: Steroid
- Subclass: Bufadienolide
| Canonical Smiles | O=c1ccc(co1)[C@H]1CC[C@]2([C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CCC=C2)O |
|---|---|
| InChI | InChI=1S/C24H30O3/c1-22-12-4-3-5-17(22)7-8-20-19(22)10-13-23(2)18(11-14-24(20,23)26)16-6-9-21(25)27-15-16/h3,5-7,9,15,18-20,26H,4,8,10-14H2,1-2H3/t18-,19+,20-,22+,23-,24+/m1/s1 |
| InChIKey | KBOQXVVZFSWICE-FIJLXMTKSA-N |
| Formula | C24H30O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 366.5 |
| Rotatable Bonds | 1 |
| TPSA | 50.44 |
| LogP | 4.97 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.62 |
| Exact Mass | 366.22 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Drimiopsis maculata, Eucomis schiffii, Urginea epigea, Drimia altissima | Hyacinthaceae | Plantae | — |
| 2 | Urginea epigea | Hyacinthaceae | Plantae | 2895781 |
Showing of synonyms
14beta-hydroxybufa-3,5,20,22-tetraenolide
- Pohl T, Koorbanally C, et al. (2001). Bufadienolides from Drimia robusta and Urginea. Phytochemistry, 2001, 58(4), 557–561. [View]
- Fusi F, Ferrara A, et al. (2008). Vascular myorelaxing activity of isolates from South African Hyacinthaceae partly mediated by activation of soluble guanylyl cyclase in rat aortic ring preparations. Journal of pharmacy and pharmacology, 2008, 60(4), 489–497. [View]
No compound-protein relationship available.
SMILES: C1CC=CC(=CC2)C1C(CC3)C2C(C34)CCC4c5ccc(=O)oc5
Level: 1
Mol. Weight: 366.5 g/mol
SMILES: C1CCC(C12)CCC3C2CC=C4C3CCC=C4
Level: 0
Mol. Weight: 366.5 g/mol
SMILES: O=c1cccco1
Level: 0
Mol. Weight: 366.5 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.81
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.31
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.37
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.35
- Plasma Protein Binding
- 77.74
- 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
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.68
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.77
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.27
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.3
- 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
- -10.92
- Rat (Acute)
- 2.6
- Rat (Chronic Oral)
- 1.54
- Fathead Minnow
- 3.92
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 449.99
- Hydration Free Energy
- -4.9
- Log(D) at pH=7.4
- 4.22
- Log(P)
- 4.2
- Log S
- -5.72
- Log(Vapor Pressure)
- -7.94
- Melting Point
- 204.25
- pKa Acid
- 9.42
- pKa Basic
- 7.37
| 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 | 0.9394 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9332 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8884 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8562 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8369 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8300 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8249 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7763 |
| High affinity 3',5'-cyclic-AMP phosphodiesterase 7A | Q13946 | PDE7A_HUMAN | Homo sapiens | 3 | 0.7739 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.7672 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7663 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7626 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7548 |
| 17-beta-hydroxysteroid dehydrogenase 14 | Q9BPX1 | DHB14_HUMAN | Homo sapiens | 2 | 0.7507 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7483 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7458 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7442 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7421 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7333 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7332 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7328 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 2 | 0.7302 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.7281 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7267 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 2 | 0.7194 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7189 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 2 | 0.7134 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7125 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.7123 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 2 | 0.7121 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7117 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7051 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7033 |
| Class B acid phosphatase | Q540U1 | APHA_SALTM | Salmonella typhimurium | 2 | 0.7032 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7021 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7021 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7009 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7006 |