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6alpha-acetoxy-3beta,8beta,14beta-trihydroxy-10,13-dimethylbufa-4,20,22-trienolide 3-O-beta-D-glucopyranoside
- Family: Plantae - Asparagaceae
- Kingdom: Plantae
-
Class: Steroid
- Subclass: Sterol Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@H]2CC[C@]3(C(=C2)[C@@H](OC(=O)C)C[C@@]2([C@@H]3CC[C@]3([C@]2(O)CC[C@@H]3c2ccc(=O)oc2)C)O)C)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C32H44O12/c1-16(34)42-21-13-31(39)23(8-10-30(3)19(7-11-32(30,31)40)17-4-5-24(35)41-15-17)29(2)9-6-18(12-20(21)29)43-28-27(38)26(37)25(36)22(14-33)44-28/h4-5,12,15,18-19,21-23,25-28,33,36-40H,6-11,13-14H2,1-3H3/t18-,19+,21-,22+,23+,25+,26-,27+,28+,29-,30+,31-,32+/m0/s1 |
| InChIKey | LSMIOFMZNVEEBR-SAUSJFMBSA-N |
| Formula | C32H44O12 |
| HBA | 12 |
| HBD | 6 |
| MW | 620.69 |
| Rotatable Bonds | 5 |
| TPSA | 196.35 |
| LogP | 0.64 |
| Number Rings | 6 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 44 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.75 |
| Exact Mass | 620.28 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Rhodocodon rotundus | Asparagaceae | Plantae | 1069049 |
Showing of synonyms
6alpha-acetoxy-3beta,8beta,14beta-trihydroxy-10,13-dimethylbufa-4,20,22-trienolide 3-O-beta-D-glucopyranoside
- Whitmore H, Sishtla K, et al. (2020). Bufadienolides and anti-angiogenic homoisoflavonoids from Rhodocodon cryptopodus, Rhodocodon rotundus and Rhodocodon cyathiformis. Fitoterapia, 2020, 141, 104479. [View]
No compound-protein relationship available.
SMILES: c1oc(=O)ccc1C2CCC(C23)C4C(CC3)C5C(CC4)=CC(CC5)OC6CCCCO6
Level: 2
Mol. Weight: 620.69 g/mol
SMILES: C1CCC(C12)CCC3C2CCC=4C3CCC(C4)OC5CCCCO5
Level: 1
Mol. Weight: 620.69 g/mol
SMILES: C1CCC=C(CC2)C1C(CC3)C2C(C34)CCC4c5ccc(=O)oc5
Level: 1
Mol. Weight: 620.69 g/mol
SMILES: C1CCC(C12)CCC3C2CCC=4C3CCCC4
Level: 0
Mol. Weight: 620.69 g/mol
SMILES: O=c1cccco1
Level: 0
Mol. Weight: 620.69 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 620.69 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.51
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.910
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 13.6
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.760
- Plasma Protein Binding
- 88.56
- 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
- 2.560
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -4.030
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.310
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.870
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Toxic
- NR-ER
- Toxic
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -26541.300
- Rat (Acute)
- 5.640
- Rat (Chronic Oral)
- 3.270
- Fathead Minnow
- 49.480
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 420.310
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 1.520
- Log(P)
- 0.48
- Log S
- -2.59
- Log(Vapor Pressure)
- -13.22
- Melting Point
- 216.28
- pKa Acid
- 5.87
- pKa Basic
- 6.26
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9670 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9584 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8902 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.8712 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8439 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.8187 |
| Metapyrocatechase | Q7WYF5 | Q7WYF5_9PSED | Pseudomonas alkylphenolica | 3 | 0.8132 |
| High affinity 3',5'-cyclic-AMP phosphodiesterase 7A | Q13946 | PDE7A_HUMAN | Homo sapiens | 3 | 0.8006 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7864 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7754 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7625 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7581 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.7544 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7504 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7495 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7456 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7452 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7440 |
| 17-beta-hydroxysteroid dehydrogenase 14 | Q9BPX1 | DHB14_HUMAN | Homo sapiens | 2 | 0.7432 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7432 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7430 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7407 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7363 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 2 | 0.7310 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 2 | 0.7304 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7279 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7253 |
| cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B | Q13370 | PDE3B_HUMAN | Homo sapiens | 3 | 0.7246 |
| Focal adhesion kinase 1 | Q05397 | FAK1_HUMAN | Homo sapiens | 2 | 0.7242 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 2 | 0.7229 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7179 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 2 | 0.7136 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 2 | 0.7126 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7124 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7123 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7118 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 2 | 0.7054 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 2 | 0.7034 |
| Aldo-keto reductase family 1 member A1 | P50578 | AK1A1_PIG | Sus scrofa | 3 | 0.7020 |