Azadironolide - Compound Card

Azadironolide

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Azadironolide

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
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)C1=CC(OC1=O)O)(C)C=CC(=O)C2(C)C
InChI InChI=1S/C28H36O6/c1-15(29)33-22-14-20-25(2,3)21(30)10-12-27(20,5)19-9-11-26(4)17(7-8-18(26)28(19,22)6)16-13-23(31)34-24(16)32/h8,10,12-13,17,19-20,22-23,31H,7,9,11,14H2,1-6H3/t17-,19+,20-,22+,23?,26-,27+,28-/m0/s1
InChIKey NIASTLFJLAWIRP-GQILNQLCSA-N
Formula C28H36O6
HBA 6
HBD 1
MW 468.59
Rotatable Bonds 2
TPSA 89.9
LogP 4.28
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 468.25
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Turraea robusta Meliaceae Plantae 1899148

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: 10814144

No compound-protein relationship available.

Structure

SMILES: O=C1OCC=C1C(CC2)C(C=23)CCC4C3CCC5C4C=CC(=O)C5

Level: 1

Mol. Weight: 468.59 g/mol

Structure

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

Level: 0

Mol. Weight: 468.59 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 468.59 g/mol

Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.87
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.64
Plasma Protein Binding
81.16
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.38
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.01
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.07
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.43
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-176.22
Rat (Acute)
2.58
Rat (Chronic Oral)
1.74
Fathead Minnow
3.97
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
492.3
Hydration Free Energy
-2.77
Log(D) at pH=7.4
3.61
Log(P)
3.63
Log S
-5.61
Log(Vapor Pressure)
-8.68
Melting Point
238.21
pKa Acid
8.32
pKa Basic
4.42
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9274
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9274
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7794
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7794
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7071
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7071

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