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Riparianin
- Family: Plantae - Hyacinthaceae:Urgineoideae
- Kingdom: Plantae
-
Class: Steroid
- Subclass: Bufadienolide
| Canonical Smiles | CO[C@@]12O[C@@H]3C=C4CC[C@@H]5[C@@H]([C@]4(C[C@H]3O[C@@H]([C@@H]1O)O[C@H]([C@H]2O)C)C)[C@H](O)C(=O)[C@]1([C@]5(O)C[C@@H]([C@@H]1c1ccc(=O)oc1)OC(=O)C)C |
|---|---|
| InChI | InChI=1S/C33H42O13/c1-14-26(37)33(41-5)28(39)29(43-14)45-20-11-30(3)17(10-19(20)46-33)7-8-18-24(30)25(36)27(38)31(4)23(16-6-9-22(35)42-13-16)21(44-15(2)34)12-32(18,31)40/h6,9-10,13-14,18-21,23-26,28-29,36-37,39-40H,7-8,11-12H2,1-5H3/t14-,18+,19+,20+,21-,23-,24+,25-,26+,28-,29-,30-,31-,32-,33-/m0/s1 |
| InChIKey | MXRQWOBJNWUMFK-QDWXTXCPSA-N |
| Formula | C33H42O13 |
| HBA | 13 |
| HBD | 4 |
| MW | 646.69 |
| Rotatable Bonds | 3 |
| TPSA | 191.42 |
| LogP | 0.7 |
| Number Rings | 7 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 46 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.73 |
| Exact Mass | 646.26 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Urginea riparia | Hyacinthaceae:Urgineoideae | Plantae | 72879 |
Showing of synonyms
Riparianin
- Crouch NR, Langlois A, et al. (2007). Bufadienolides from Drimia macrocentra and Urginea riparia (Hyacinthaceae: Urgineoideae). Phytochemistry, 2007, 68(13), 1731–1734. [View]
Pubchem:
101437110
No compound-protein relationship available.
SMILES: c1oc(=O)ccc1C2CCC(C23)C4C(CC3=O)C5C(CC4)=CC6C(C5)OC7CC(O6)CCO7
Level: 1
Mol. Weight: 646.69 g/mol
SMILES: C1CCC(C12)C3C(CC2=O)C4C(CC3)=CC5C(C4)OC6CC(O5)CCO6
Level: 0
Mol. Weight: 646.69 g/mol
SMILES: O=c1cccco1
Level: 0
Mol. Weight: 646.69 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.73
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.8
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 38.92
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.71
- Plasma Protein Binding
- 89.85
- 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
- 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
- 4.2
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.69
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.31
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.79
- 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
- Toxic
- T. Pyriformis
- -74868.18
- Rat (Acute)
- 5.09
- Rat (Chronic Oral)
- 2.94
- Fathead Minnow
- 107.67
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 4159.94
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 1.64
- Log(P)
- 0.82
- Log S
- -3.38
- Log(Vapor Pressure)
- -129.58
- Melting Point
- 255.05
- pKa Acid
- 5.41
- pKa Basic
- 3.31
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Purine nucleoside phosphorylase | Q8I3X4 | Q8I3X4_PLAF7 | Plasmodium falciparum | 3 | 0.7995 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7831 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.7709 |
| Purine nucleoside phosphorylase DeoD-type | Q5EEL8 | DEOD_BACCE | Bacillus cereus | 3 | 0.7564 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7544 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7499 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7451 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7434 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7430 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7383 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7376 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7349 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7332 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.7327 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.7315 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7195 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 2 | 0.7188 |
| Focal adhesion kinase 1 | Q05397 | FAK1_HUMAN | Homo sapiens | 2 | 0.7142 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7058 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7006 |