12alpha-acetoxy-1,2-dihydroazadirone - Compound Card

12alpha-acetoxy-1,2-dihydroazadirone

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12alpha-acetoxy-1,2-dihydroazadirone

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([C@H](C3)OC(=O)C)C)c1ccoc1)(C)CCC(=O)C2(C)C
InChI InChI=1S/C30H40O6/c1-17(31)35-25-15-23-28(5)12-10-24(33)27(3,4)22(28)14-26(36-18(2)32)30(23,7)21-9-8-20(29(21,25)6)19-11-13-34-16-19/h9,11,13,16,20,22-23,25-26H,8,10,12,14-15H2,1-7H3/t20-,22-,23+,25-,26+,28-,29-,30-/m0/s1
InChIKey XDCVATVSSWQVBN-UUVGBLLGSA-N
Formula C30H40O6
HBA 6
HBD 0
MW 496.64
Rotatable Bonds 3
TPSA 82.81
LogP 6.0
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 496.28
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Turraea parvifolia Meliaceae Plantae 201020

Showing of synonyms

  • Cheplogoi PK, Mulholland DA. (2003). Limonoids from Turraea parvifolia (Meliaceae). Biochemical Systematics and Ecology,2003,31,799-803. [View] [PubMed]
Pubchem: 14109466

No compound-protein relationship available.

Structure

SMILES: c1occc1C(CC2)C(C=23)CCC4C3CCC5C4CCC(=O)C5

Level: 1

Mol. Weight: 496.64 g/mol

Structure

SMILES: C1CCC(C=12)CCC3C2CCC4C3CCC(=O)C4

Level: 0

Mol. Weight: 496.64 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 496.64 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.71
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.34
Plasma Protein Binding
89.25
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
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
12.13
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.54
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.25
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.86
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
Safe
T. Pyriformis
-512.63
Rat (Acute)
2.78
Rat (Chronic Oral)
2.06
Fathead Minnow
4.8
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
471.3
Hydration Free Energy
-2.95
Log(D) at pH=7.4
4.43
Log(P)
4.91
Log S
-5.66
Log(Vapor Pressure)
-8.58
Melting Point
188.63
pKa Acid
10.3
pKa Basic
4.7
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8323
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8323
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7780
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7780
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7513
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7513
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7506
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7506
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7484
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7484
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7424
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7424
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7362
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7362
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7256
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7256
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7214
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7214
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7174
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7174
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7142
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7142
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7123
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7123
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7034
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7034
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7029
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7029

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