12alpha-acetoxy-7-deacetylazadirone - Compound Card

12alpha-acetoxy-7-deacetylazadirone

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12alpha-acetoxy-7-deacetylazadirone

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles CC(=O)O[C@@]12CC[C@@H]3[C@](C2=CC[C@@H]1c1cocc1)(C)[C@@H](O)C[C@H]1[C@@]3(C)C=CC(=O)C1(C)C
InChI InChI=1S/C27H34O5/c1-16(28)32-27-12-8-19-25(4)11-9-22(29)24(2,3)21(25)14-23(30)26(19,5)20(27)7-6-18(27)17-10-13-31-15-17/h7,9-11,13,15,18-19,21,23,30H,6,8,12,14H2,1-5H3/t18-,19+,21-,23+,25+,26+,27+/m1/s1
InChIKey PHAOQQRISDLODR-LLPUIJAFSA-N
Formula C27H34O5
HBA 5
HBD 1
MW 438.56
Rotatable Bonds 2
TPSA 76.74
LogP 4.96
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.63
Exact Mass 438.24
Number of Lipinski Rule Violations 0
# 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]

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 438.56 g/mol

Structure

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

Level: 0

Mol. Weight: 438.56 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 438.56 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.66
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
-1.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.29
Plasma Protein Binding
80.06
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
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
12.44
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.41
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.45
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
7.04
Micronucleos
Toxic
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
-93.26
Rat (Acute)
3.41
Rat (Chronic Oral)
1.93
Fathead Minnow
3.94
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
456.4
Hydration Free Energy
-3.02
Log(D) at pH=7.4
3.84
Log(P)
4.32
Log S
-5.05
Log(Vapor Pressure)
-8.43
Melting Point
189.95
pKa Acid
9.56
pKa Basic
5.08
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9083
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9083
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7645
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7645
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7565
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7565
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7536
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7536
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7461
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7461
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7452
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7452
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7302
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7302
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7294
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7294
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7292
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7292
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7187
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7187
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7165
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7165

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