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Hellebrigenin 3-acetate
- Family: Plantae - Melianthaceae
- Kingdom: Plantae
- Class: Steroid
| Canonical Smiles | O=C[C@@]12CC[C@@H](C[C@@]2(O)CC[C@@H]2[C@@H]1CC[C@]1([C@]2(O)CC[C@@H]1c1ccc(=O)oc1)C)OC(=O)C |
|---|---|
| InChI | InChI=1S/C26H34O7/c1-16(28)33-18-5-10-24(15-27)20-6-9-23(2)19(17-3-4-22(29)32-14-17)8-12-26(23,31)21(20)7-11-25(24,30)13-18/h3-4,14-15,18-21,30-31H,5-13H2,1-2H3/t18-,19+,20-,21+,23+,24-,25-,26-/m0/s1 |
| InChIKey | VIOBLZMEZRNYRR-XDFZRXKSSA-N |
| Formula | C26H34O7 |
| HBA | 7 |
| HBD | 2 |
| MW | 458.55 |
| Rotatable Bonds | 3 |
| TPSA | 114.04 |
| LogP | 3.11 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.73 |
| Exact Mass | 458.23 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Bersama abyssinica | Melianthaceae | Plantae | 113247 |
| 2 | Bersama abyssinica | Melianthaceae | Plantae | 113247 |
Showing of synonyms
Hellebrigenin 3-acetate
4064-09-9
Hellebrigenin, 3-acetate
[(3S,5S,8R,9S,10S,13R,14S,17R)-10-formyl-5,14-dihydroxy-13-methyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
AC1Q6ASK
HELLEBRIGENIN-3-ACETATE
AC1L6I64
CHEBI:5644
NSC106676
NSC-106676
C08867
Q27106846
5.beta.-Bufa-20, 3.beta.,5,14-trihydroxy-19-oxo-, 3-acetate
Bufa-20, 3-(acetyloxy)-5,14-dihydroxy-19-oxo-, (3.beta.,5.beta.)-
- Kupchan SM, Hemingway RJ, et al. (1968). The isolation and characterization of hellebrigenin 3-acetate and hellebrigenin 3, 5-diacetate, bufadienolide tumor inhibitors from Bersama abyssinica.. Tetrahedron letters,1968,9(2),149-152. [View] [PubMed]
- Kupchan SM, Hemingway RJ, et al. (1969). XLIV. Isolation and characterization of hellebrigenin 3-acetate and hellebrigenin 3, 5-diacetate, Bufadienolide tumor inhibitors from Bersama abyssinica.. The Journal of organic chemistry,1969,34(12),3894-3898. [View] [PubMed]
No compound-protein relationship available.
SMILES: C1CCCC(CC2)C1C(CC3)C2C(C34)CCC4c5ccc(=O)oc5
Level: 1
Mol. Weight: 458.55 g/mol
SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4
Level: 0
Mol. Weight: 458.55 g/mol
SMILES: O=c1cccco1
Level: 0
Mol. Weight: 458.55 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.95
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.7
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.69
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.6
- Plasma Protein Binding
- 68.85
- 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
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.42
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.43
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.25
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.84
- Micronucleos
- Toxic
- 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
- -148.82
- Rat (Acute)
- 5.68
- Rat (Chronic Oral)
- 1.4
- Fathead Minnow
- 3.97
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 478.86
- Hydration Free Energy
- -3.02
- Log(D) at pH=7.4
- 2.06
- Log(P)
- 1.89
- Log S
- -4.17
- Log(Vapor Pressure)
- -9.45
- Melting Point
- 228.46
- pKa Acid
- 7.14
- pKa Basic
- 6.72
| 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 | 0.9477 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9477 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9346 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9346 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8402 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8402 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8192 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8192 |
| High affinity 3',5'-cyclic-AMP phosphodiesterase 7A | Q13946 | PDE7A_HUMAN | Homo sapiens | 3 | 0.7706 |
| High affinity 3',5'-cyclic-AMP phosphodiesterase 7A | Q13946 | PDE7A_HUMAN | Homo sapiens | 3 | 0.7706 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7583 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7583 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7575 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7575 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7506 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7506 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7492 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7492 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7453 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7453 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7444 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7444 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7444 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7444 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7343 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7343 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 2 | 0.7338 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 2 | 0.7338 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7290 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7290 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7265 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7265 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7206 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7206 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7195 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7195 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7122 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7122 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.7104 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.7104 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7070 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7070 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 2 | 0.7045 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 2 | 0.7045 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 2 | 0.7021 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 2 | 0.7021 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 2 | 0.7002 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 2 | 0.7002 |