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Prototiamin C
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpenoid
| Canonical Smiles | CC(=O)O[C@@H]1C[C@@H]2[C@]([C@@H]3[C@]1(C)C1=CC[C@H]([C@]1(C)CC3)[C@@H]1C[C@@H](OC1=O)[C@@H]1OC1(C)C)(C)C=CC(=O)C2(C)C |
|---|---|
| InChI | InChI=1S/C32H44O6/c1-17(33)36-25-16-23-28(2,3)24(34)12-14-31(23,7)22-11-13-30(6)19(9-10-21(30)32(22,25)8)18-15-20(37-27(18)35)26-29(4,5)38-26/h10,12,14,18-20,22-23,25-26H,9,11,13,15-16H2,1-8H3/t18-,19-,20+,22+,23-,25+,26-,30-,31+,32-/m0/s1 |
| InChIKey | XSENKEHAQYTOPY-QAPXOFNMSA-N |
| Formula | C32H44O6 |
| HBA | 6 |
| HBD | 0 |
| MW | 524.7 |
| Rotatable Bonds | 3 |
| TPSA | 82.2 |
| LogP | 5.59 |
| Number Rings | 6 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 38 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.78 |
| Exact Mass | 524.31 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Entandrophragma congoënse | Meliaceae | Plantae | 2590899 |
| 2 | Entandrophragma congoense | Meliaceae | Plantae | 2590899 |
Showing of synonyms
Prototiamin C
CHEMBL3581612
[(5R,7R,8R,9R,10R,13S,17S)-17-[(3S,5R)-5-[(2S)-3,3-dimethyloxiran-2-yl]-2-oxo-tetrahydrofuran-3-yl]-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-yl] acetate
No compound-protein relationship available.
SMILES: O1CC1C(O2)CC(C2=O)C(CC3)C(C=34)CCC5C4CCC6C5C=CC(=O)C6
Level: 2
Mol. Weight: 524.7 g/mol
SMILES: O1CCC(C1=O)C(CC2)C(C=23)CCC4C3CCC5C4C=CC(=O)C5
Level: 1
Mol. Weight: 524.7 g/mol
SMILES: O1CC1C(O2)CCC2=O
Level: 1
Mol. Weight: 524.7 g/mol
SMILES: C1CCC(C=12)CCC3C2CCC4C3C=CC(=O)C4
Level: 0
Mol. Weight: 524.7 g/mol
SMILES: O=C1CCCO1
Level: 0
Mol. Weight: 524.7 g/mol
SMILES: C1CO1
Level: 0
Mol. Weight: 524.7 g/mol
Anti-plasmodial
Absorption
- Caco-2 (logPapp)
- -5.19
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.93
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.41
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.05
- Plasma Protein Binding
- 67.64
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- 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
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.09
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.97
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.44
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 8.12
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Toxic
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -1089.38
- Rat (Acute)
- 3.08
- Rat (Chronic Oral)
- 1.68
- Fathead Minnow
- 6.29
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 507.96
- Hydration Free Energy
- -2.89
- Log(D) at pH=7.4
- 4.62
- Log(P)
- 4.76
- Log S
- -6.68
- Log(Vapor Pressure)
- -8.18
- Melting Point
- 211.3
- pKa Acid
- 7.06
- pKa Basic
- 4.37
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7716 |
| Retinol-binding protein 1 | P09455 | RET1_HUMAN | Homo sapiens | 3 | 0.7309 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7275 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7064 |