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Bryoniaoside A
- Family: Plantae - Cucurbitaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@H]2CC[C@@H]3C(=CC[C@@H]4[C@@]3(C)C(=O)C[C@]3([C@@]4(C)CC[C@@H]3[C@](C/C=C/C(O[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)(C)C)(O)C)C)C2(C)C)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C42H68O13/c1-21-29(45)31(47)34(50)36(52-21)55-37(2,3)16-10-17-41(8,51)25-15-18-39(6)26-13-11-22-23(42(26,9)27(44)19-40(25,39)7)12-14-28(38(22,4)5)54-35-33(49)32(48)30(46)24(20-43)53-35/h10-11,16,21,23-26,28-36,43,45-51H,12-15,17-20H2,1-9H3/b16-10+/t21-,23+,24+,25-,26-,28-,29-,30+,31+,32-,33+,34+,35-,36-,39-,40+,41-,42-/m0/s1 |
| InChIKey | HASGCQFWZRNVTG-WUCDEJKUSA-N |
| Formula | C42H68O13 |
| HBA | 13 |
| HBD | 8 |
| MW | 780.99 |
| Rotatable Bonds | 9 |
| TPSA | 215.83 |
| LogP | 2.28 |
| Number Rings | 6 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 55 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.88 |
| Exact Mass | 780.47 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Bryonia cretica | Cucurbitaceae | Plantae | 61884 |
Showing of synonyms
Bryoniaoside A
- Matsuda H, Nakashima S, et al. (2010). Cucurbitane-Type Triterpenes with Anti-proliferative Effects on U937 Cells from an Egyptian Natural Medicine, Bryonia cretica: Structures of New Triterpene Glycosides, Bryoniaosides A and B. Chemical & pharmaceutical bulletin, 2010, 58(5), 747-51. [View] [PubMed]
No compound-protein relationship available.
SMILES: O1CCCCC1OCC=CCCC2CCC(C23)C4C(C(=O)C3)C5C(=CC4)CC(CC5)OC6CCCCO6
Level: 2
Mol. Weight: 780.99 g/mol
SMILES: O1CCCCC1OCC=CCCC2CCC(C23)C4C(C(=O)C3)C5C(=CC4)CCCC5
Level: 1
Mol. Weight: 780.99 g/mol
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3CCC(C4)OC5CCCCO5
Level: 1
Mol. Weight: 780.99 g/mol
SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3CCCC4
Level: 0
Mol. Weight: 780.99 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 780.99 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.22
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- 3.900
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 1253.72
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.930
- Plasma Protein Binding
- 110.67
- 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
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 2.080
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -29.810
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.950
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.540
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- 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
- -2277299.630
- Rat (Acute)
- 4.690
- Rat (Chronic Oral)
- 3.810
- Fathead Minnow
- 2881.230
- 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
- 253187.280
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 3.780
- Log(P)
- 2.4
- Log S
- -3.38
- Log(Vapor Pressure)
- -8215.73
- Melting Point
- 239.29
- pKa Acid
- -19.36
- pKa Basic
- 6.74
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8033 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7958 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7706 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7602 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7399 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7368 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7278 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7115 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7087 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7035 |