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Azadiradione
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Limonoid
| Canonical Smiles | CC(=O)O[C@@H]1C[C@@H]2[C@]([C@@H]3[C@]1(C)C1=CC(=O)[C@H]([C@@]1(CC3)C)c1ccoc1)(C)C=CC(=O)C2(C)C |
|---|---|
| InChI | InChI=1S/C28H34O5/c1-16(29)33-23-14-20-25(2,3)22(31)8-11-26(20,4)19-7-10-27(5)21(28(19,23)6)13-18(30)24(27)17-9-12-32-15-17/h8-9,11-13,15,19-20,23-24H,7,10,14H2,1-6H3/t19-,20+,23-,24-,26-,27-,28-/m1/s1 |
| InChIKey | KWAMDQVQFVBEAU-HMWIRDDCSA-N |
| Formula | C28H34O5 |
| HBA | 5 |
| HBD | 0 |
| MW | 450.58 |
| Rotatable Bonds | 2 |
| TPSA | 73.58 |
| LogP | 5.42 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.61 |
| Exact Mass | 450.24 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Quivisia papinae | Meliaceae | Plantae | — |
Showing of synonyms
Azadiradione
26241-51-0
CHEBI:67280
[(5R,7R,8R,9R,10R,13S,17R)-17-(furan-3-yl)-4,4,8,10,13-pentamethyl-3,16-dioxo-6,7,9,11,12,17-hexahydro-5H-cyclopenta[a]phenanthren-7-yl] acetate
(5alpha,7alpha,13alpha,17alpha)-17-(furan-3-yl)-4,4,8-trimethyl-3,16-dioxoandrosta-1,14-dien-7-yl acetate
24-Nor-5alpha,13alpha,17alpha-chola-1,14,20,22-tetraene-3,16-dione, 21,23-epoxy-7alpha-hydroxy-4,4,8-trimethyl-,acetate
((5R,7R,8R,9R,10R,13S,17R)-17-(furan-3-yl)-4,4,8,10,13-pentamethyl-3,16-dioxo-6,7,9,11,12,17-hexahydro-5H-cyclopenta(a)phenanthren-7-yl) acetate
24-Nor-5alpha,13alpha,17alpha-chola-1,14,20,22-tetraene-3,16-dione, 21,23-epoxy-7alpha-hydroxy-4,4,8-trimethyl-, acetate
Azadiradione (~90%)
24-Norchola-1,14,20,22-tetraene-3,16-dione, 7-(acetyloxy)-21,23-epoxy-4,4,8-trimethyl-, (5alpha,7alpha,13alpha,17alpha)-
(5a,7a,13a,17a)-7-(Acetyloxy)-21,23-epoxy-4,4,8-trimethyl-24-norchola-1,14,20,22-tetraene-3,16-dione
CHEMBL1215754
BDBM92410
C28H34O5
HY-N9615
AKOS040763659
AT40289
TS-10154
Q27135739
(5alpha\,7alpha\,13alpha\,17alpha)-17-(furan-3-yl)-4\,4\,8-trimethyl-3\,16-dioxoandrosta-1\,14-dien-7-yl acetate
24-Norchola-1,14,20,22-tetraene-3,16-dione, 7-(acetyloxy)-21,23-epoxy-4,4,8-trimethyl-, (5|A,7|A,13|A,17|A)-
- Coombes PH, Mulholland DA, et al. (2004). Quivisianthone, an evodulone limonoid from the Madagascan MeliaceaeQuivisia papinae. Phytochemistry, 2004, 65(4), 377–380. [View]
Pubchem:
12308714
Cas:
26241-51-0
Zinc:
ZINC000031495483
Chebi:
67280
Nmrshiftdb2:
60020335
Metabolights:
MTBLC67280
Chembl:
CHEMBL1215754
Bindingdb:
92410
CPRiL:
64511
SMILES: c1occc1C(C(=O)C2)C(C=23)CCC4C3CCC5C4C=CC(=O)C5
Level: 1
Mol. Weight: 450.58 g/mol
SMILES: C1C(=O)CC(C=12)CCC3C2CCC4C3C=CC(=O)C4
Level: 0
Mol. Weight: 450.58 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 450.58 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.67
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.6
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.06
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.72
- Plasma Protein Binding
- 89.84
- 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
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.39
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.85
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.22
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 7.14
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- 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
- -128.35
- Rat (Acute)
- 2.7
- Rat (Chronic Oral)
- 2.14
- Fathead Minnow
- 4.09
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 471.85
- Hydration Free Energy
- -2.78
- Log(D) at pH=7.4
- 4.02
- Log(P)
- 3.74
- Log S
- -5.36
- Log(Vapor Pressure)
- -8.68
- Melting Point
- 216.09
- pKa Acid
- 8.71
- pKa Basic
- 4.25
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8874 |
| Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial | Q33862 | Q33862_ASCSU | Ascaris suum | 3 | 0.8439 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8367 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 3 | 0.7934 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7794 |
| Oxygen-insensitive NAD(P)H nitroreductase | P38489 | NFSB_ECOLI | Escherichia coli | 3 | 0.7576 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7354 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7354 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7327 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7285 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7247 |