Azadirone - Compound Card

Azadirone

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Azadirone

Structure
Zoomed Structure
  • 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[C@H]([C@@]1(CC3)C)c1ccoc1)(C)C=CC(=O)C2(C)C
InChI InChI=1S/C28H36O4/c1-17(29)32-24-15-22-25(2,3)23(30)10-13-27(22,5)21-9-12-26(4)19(18-11-14-31-16-18)7-8-20(26)28(21,24)6/h8,10-11,13-14,16,19,21-22,24H,7,9,12,15H2,1-6H3/t19-,21+,22-,24+,26-,27+,28-/m0/s1
InChIKey XXIKKMLIDXLAIK-RFKFVWFBSA-N
Formula C28H36O4
HBA 4
HBD 0
MW 436.59
Rotatable Bonds 2
TPSA 56.51
LogP 6.24
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 436.26
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Turraea robusta Meliaceae Plantae 1899148
2 Turraea nilotica Meliaceae Plantae 992803

Showing of synonyms

  • Irungu BN, Adipo N, et al. (2015). Antiplasmodial and cytotoxic activities of the constituents of Turraea robusta and Turraea nilotica.. Journal of Ethnopharmacology,2015,174,419-425. [View] [PubMed]
Pubchem: 10906239
Chebi: 76293
Nmrshiftdb2: 60020331
Metabolights: MTBLC76293
CPRiL: 215207
Structure

SMILES: c1occc1C(CC2)C(C=23)CCC4C3CCC5C4C=CC(=O)C5

Level: 1

Mol. Weight: 436.59 g/mol

Structure

SMILES: C1CCC(C=12)CCC3C2CCC4C3C=CC(=O)C4

Level: 0

Mol. Weight: 436.59 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 436.59 g/mol

Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.97

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.91
Plasma Protein Binding
86.03
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
10.73
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.41
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.09
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.4
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
Toxic
T. Pyriformis
-90.28
Rat (Acute)
2.51
Rat (Chronic Oral)
1.96
Fathead Minnow
4.03
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
459.37
Hydration Free Energy
-2.91
Log(D) at pH=7.4
5.02
Log(P)
5.46
Log S
-6.22
Log(Vapor Pressure)
-8.2
Melting Point
179.21
pKa Acid
10.17
pKa Basic
5.31
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8530
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8530
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8129
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8129
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7875
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7875
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7824
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7824
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7804
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7804
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7769
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7769
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7731
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7731
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7574
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7574
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7559
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7559
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7547
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7547
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7542
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7542
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7468
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7468
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7403
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7403
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7392
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7392
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7382
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7382
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7373
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7373
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7261
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7261
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7248
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7248
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7245
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7245
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7236
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7236
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7218
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7218
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7217
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7217
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7193
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7193
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7172
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7172
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7049
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7049
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7044
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7044
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7042
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7042
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7013
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7013

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