6-acetoxy methyl angolensate - Compound Card

6-acetoxy methyl angolensate

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6-acetoxy methyl angolensate

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles COC(=O)C([C@@H]1[C@@]2(C)[C@H](CC(=O)C1(C)C)O[C@]13C(=C)[C@@H]2CC[C@@]3(C)[C@@H](OC(=O)C1)c1cocc1)OC(=O)C
InChI InChI=1S/C29H36O9/c1-15-18-8-10-27(5)24(17-9-11-35-14-17)37-21(32)13-29(15,27)38-20-12-19(31)26(3,4)23(28(18,20)6)22(25(33)34-7)36-16(2)30/h9,11,14,18,20,22-24H,1,8,10,12-13H2,2-7H3/t18-,20-,22?,23-,24-,27-,28+,29-/m0/s1
InChIKey QSQFOIMEVMOMIJ-AJZQVFHJSA-N
Formula C29H36O9
HBA 9
HBD 0
MW 528.6
Rotatable Bonds 4
TPSA 118.34
LogP 4.1
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.66
Exact Mass 528.24
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Khaya senegalensis Meliaceae Plantae 587579

Showing of synonyms

  • Abdelgaleil SAM, Okamura H, et al. (2001). Khayanolides, rearranged phragmalin limonoid antifeedants from Khaya senegalensis. Tetrahedron,2001,57(1),119-126. [View]
Pubchem: 163016586

No compound-protein relationship available.

Structure

SMILES: C1CC(=O)CC(O2)C1C(C3=C)CCC(C234)C(OC(=O)C4)c5ccoc5

Level: 1

Mol. Weight: 528.6 g/mol

Structure

SMILES: C1CC(=O)CC(O2)C1C(C3=C)CCC(C234)COC(=O)C4

Level: 0

Mol. Weight: 528.6 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 528.6 g/mol

Antifeedant

Absorption

Caco-2 (logPapp)
-5.07
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.22

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.910
Plasma Protein Binding
77.63
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
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.370
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.030
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.170
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.060
Micronucleos
Toxic
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
-1236.790
Rat (Acute)
4.170
Rat (Chronic Oral)
2.090
Fathead Minnow
6.540
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
447.280
Hydration Free Energy
-2.840
Log(D) at pH=7.4
2.760
Log(P)
3.45
Log S
-5.19
Log(Vapor Pressure)
-9.0
Melting Point
220.28
pKa Acid
6.23
pKa Basic
3.44
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7830
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7830
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7717
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7717
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7597
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7597
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7351
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7351
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7348
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7348
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7295
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7295
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7285
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7285
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7221
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7221
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7171
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7171
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7147
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7147
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7143
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7143
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.7124
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.7124
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.7037
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.7037
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7006
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7006

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