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3,4-secotirucalla-23-oxo-4(28),7,24-trien-3,21-dioic acid (21-methyl ester)
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | COC(=O)[C@H]([C@@H]1CC[C@]2([C@@]1(C)CC[C@H]1C2=CC[C@H]([C@]1(C)CCC(=O)O)C(=C)C)C)CC(=O)C=C(C)C |
|---|---|
| InChI | InChI=1S/C31H46O5/c1-19(2)17-21(32)18-22(28(35)36-8)24-11-15-31(7)26-10-9-23(20(3)4)29(5,14-13-27(33)34)25(26)12-16-30(24,31)6/h10,17,22-25H,3,9,11-16,18H2,1-2,4-8H3,(H,33,34)/t22-,23-,24-,25-,29-,30-,31+/m0/s1 |
| InChIKey | DAQCFFGRXTVWBG-MMOXWZNWSA-N |
| Formula | C31H46O5 |
| HBA | 4 |
| HBD | 1 |
| MW | 498.7 |
| Rotatable Bonds | 9 |
| TPSA | 80.67 |
| LogP | 6.93 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 36 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.71 |
| Exact Mass | 498.33 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Entandrophragma angolense | Meliaceae | Plantae | 587577 |
Showing of synonyms
3,4-secotirucalla-23-oxo-4(28),7,24-trien-3,21-dioic acid (21-methyl ester)
- Orisadipe AT, Adesomoju AA, et al. (2005). Tirucallane triterpenes from the leaf extract of Entandrophragma angolense. Phytochemistry,2005,66(19),2324-2328. [View]
No compound-protein relationship available.
SMILES: C1CCC(C12)CCC3C2=CCCC3
Level: 0
Mol. Weight: 498.7 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.33
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.000
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.71
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 2.150
- Plasma Protein Binding
- 103.31
- 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
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 1.570
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.310
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.650
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.510
- Micronucleos
- Safe
- 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
- -246.950
- Rat (Acute)
- 3.030
- Rat (Chronic Oral)
- 2.010
- Fathead Minnow
- 4.020
- 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
- 498.100
- Hydration Free Energy
- -3.090
- Log(D) at pH=7.4
- 3.710
- Log(P)
- 6.48
- Log S
- -5.75
- Log(Vapor Pressure)
- -9.78
- Melting Point
- 181.76
- pKa Acid
- 7.96
- pKa Basic
- 5.38
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8915 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8492 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.8124 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7953 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7666 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.7443 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7294 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7233 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7202 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7189 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7140 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7123 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7117 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 3 | 0.7076 |