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Turraflorin A
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Tetranortriterpenoid
| Canonical Smiles | COC(=O)C[C@@H]1[C@](C)(C=CC(=O)C1(C)C)[C@H]1[C@@H](OC(=O)C)[C@H](OC(=O)C)[C@@]2(C(=CC[C@@H]2c2cocc2)C1=C)C |
|---|---|
| InChI | InChI=1S/C31H38O8/c1-17-21-9-10-22(20-12-14-37-16-20)31(21,7)28(39-19(3)33)27(38-18(2)32)26(17)30(6)13-11-24(34)29(4,5)23(30)15-25(35)36-8/h9,11-14,16,22-23,26-28H,1,10,15H2,2-8H3/t22-,23+,26-,27-,28+,30+,31-/m1/s1 |
| InChIKey | NCVYEYGQXPQYTC-YTJYDEETSA-N |
| Formula | C31H38O8 |
| HBA | 8 |
| HBD | 0 |
| MW | 538.64 |
| Rotatable Bonds | 6 |
| TPSA | 109.11 |
| LogP | 5.1 |
| Number Rings | 4 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 39 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.55 |
| Exact Mass | 538.26 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Turraea floribunda | Meliaceae | Plantae | 992802 |
Showing of synonyms
Turraflorin A
Methyl 2-((1R,2R)-2-((1R,5R,6R,7R,7as)-6,7-bis(acetyloxy)-1-(furan-3-yl)-7a-methyl-4-methylidene-2,4,5,6,7,7a-hexahydro-1H-inden-5-yl)-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl)acetic acid
Methyl 2-((1R,2S)-2-((1R,5R,6R,7R,7aS)-6,7-diacetyloxy-1-(furan-3-yl)-7a-methyl-4-methylidene-2,5,6,7-tetrahydro-1H-inden-5-yl)-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl)acetate
Methyl 2-[(1R,2R)-2-[(1R,5R,6R,7R,7as)-6,7-bis(acetyloxy)-1-(furan-3-yl)-7a-methyl-4-methylidene-2,4,5,6,7,7a-hexahydro-1H-inden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetic acid
Methyl 2-[(1R,2S)-2-[(1R,5R,6R,7R,7aS)-6,7-diacetyloxy-1-(furan-3-yl)-7a-methyl-4-methylidene-2,5,6,7-tetrahydro-1H-inden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate
154974-37-5
CHEMBL2386306
- McFarland K, Mulholland DA, et al. (2004). Limonoids from Turraea floribunda (Meliaceae). Phytochemistry, 2004, 65(14), 2031–2037. [View]
Pubchem:
12150033
Cas:
154974-37-5
Zinc:
ZINC000096922407
Nmrshiftdb2:
70055302
Chembl:
CHEMBL2386306
No compound-protein relationship available.
SMILES: O=C1C=CC(CC1)C(C2=C)CCC(C2=3)C(CC3)c4ccoc4
Level: 2
Mol. Weight: 538.64 g/mol
SMILES: O=C1C=CC(CC1)C(C2=C)CCC(C2=3)CCC3
Level: 1
Mol. Weight: 538.64 g/mol
SMILES: C=C1CCCC(C1=2)C(CC2)c3ccoc3
Level: 1
Mol. Weight: 538.64 g/mol
SMILES: C=C1CCCC(C1=2)CCC2
Level: 0
Mol. Weight: 538.64 g/mol
SMILES: O=C1C=CCCC1
Level: 0
Mol. Weight: 538.64 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 538.64 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.6
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.720
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.6
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.190
- Plasma Protein Binding
- 92.58
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.370
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.040
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.200
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 8.360
- 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
- -1605.800
- Rat (Acute)
- 3.600
- Rat (Chronic Oral)
- 2.650
- Fathead Minnow
- 8.910
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 446.780
- Hydration Free Energy
- -2.870
- Log(D) at pH=7.4
- 3.570
- Log(P)
- 4.35
- Log S
- -5.36
- Log(Vapor Pressure)
- -8.49
- Melting Point
- 174.39
- pKa Acid
- 9.01
- pKa Basic
- 3.41
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8642 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7795 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7668 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7537 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7425 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7397 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7338 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7332 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7265 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7262 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7224 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7198 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7067 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7019 |