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Melianol
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpene
| Canonical Smiles | O[C@@H]1O[C@H](CC1[C@H]1CC[C@]2([C@@]1(C)CC[C@H]1C2=CCC2[C@]1(C)CC[C@@H](C2(C)C)O)C)C1OC1(C)C |
|---|---|
| InChI | InChI=1S/C30H48O4/c1-26(2)22-9-8-20-19(28(22,5)13-12-23(26)31)11-15-29(6)18(10-14-30(20,29)7)17-16-21(33-25(17)32)24-27(3,4)34-24/h8,17-19,21-25,31-32H,9-16H2,1-7H3/t17?,18-,19+,21-,22?,23+,24?,25-,28-,29+,30-/m1/s1 |
| InChIKey | DABHSVCBZNIZDT-WFJMIKGLSA-N |
| Formula | C30H48O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 472.71 |
| Rotatable Bonds | 2 |
| TPSA | 62.22 |
| LogP | 5.85 |
| Number Rings | 6 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.93 |
| Exact Mass | 472.36 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Quivisia papinae | Meliaceae | Plantae | — |
Showing of synonyms
Melianol
Deacetylturreanthin
16838-01-0
Melianol (tetracyclic triterpene)
(2R,5R)-5-(3,3-dimethyloxiran-2-yl)-3-[(3S,9R,10R,13S,14S,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]oxolan-2-ol
(2R,5R)-5-(3,3-dimethyloxiran-2-yl)-3-((3S,9R,10R,13S,14S,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta(a)phenanthren-17-yl)oxolan-2-ol
13a,14b,17bH-Lanost-7-ene-3b,21-diol, 21,23:24,25-diepoxy-
16868-01-0
13a,14b,17bH-Lanost-7-ene-3b,21-diol, 21,23:24,25-diepoxy-
- Coombes PH, Mulholland DA, et al. (2005). Mexicanolide limonoids from the Madagascan MeliaceaeQuivisia papinae. Phytochemistry, 2005, 66(10), 1100–1107. [View]
Pubchem:
177786
Cas:
16838-01-0
No compound-protein relationship available.
SMILES: O1CC1C2CC(CO2)C3CCC(C34)C=5C(CC4)C6C(CC5)CCCC6
Level: 2
Mol. Weight: 472.71 g/mol
SMILES: C1OCCC1C2CCC(C23)C=4C(CC3)C5C(CC4)CCCC5
Level: 1
Mol. Weight: 472.71 g/mol
SMILES: O1CC1C2CCCO2
Level: 1
Mol. Weight: 472.71 g/mol
SMILES: C1CCC(C12)CCC3C2=CCC4C3CCCC4
Level: 0
Mol. Weight: 472.71 g/mol
SMILES: C1CCOC1
Level: 0
Mol. Weight: 472.71 g/mol
SMILES: C1CO1
Level: 0
Mol. Weight: 472.71 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.15
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.65
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.43
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.62
- Plasma Protein Binding
- 59.07
- 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
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 14.52
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.95
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.54
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 6.96
- 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
- Toxic
- T. Pyriformis
- -209.2
- Rat (Acute)
- 2.62
- Rat (Chronic Oral)
- 1.56
- Fathead Minnow
- 3.87
- 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
- 467.7
- Hydration Free Energy
- -3.05
- Log(D) at pH=7.4
- 5.28
- Log(P)
- 5.95
- Log S
- -6.63
- Log(Vapor Pressure)
- -8.29
- Melting Point
- 195.94
- pKa Acid
- 7.68
- pKa Basic
- 6.78
| 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 | 0.8621 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 4 | 0.7969 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.7804 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7621 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7456 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 4 | 0.7398 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7326 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7222 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7213 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7170 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7015 |