1-O-acetylkhayanolide B - Compound Card

1-O-acetylkhayanolide B

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1-O-acetylkhayanolide B

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles COC(=O)[C@H]([C@H]1[C@@]2(C)C[C@]3([C@]1(C)C1CC[C@@]4([C@@]5([C@]1([C@H]3[C@H]([C@H]2O)O5)O)CC(=O)O[C@H]4c1ccoc1)C)OC(=O)C)O
InChI InChI=1S/C29H36O11/c1-13(30)39-27-12-24(2)19(17(32)23(34)36-5)26(27,4)15-6-8-25(3)22(14-7-9-37-11-14)38-16(31)10-28(25)29(15,35)20(27)18(40-28)21(24)33/h7,9,11,15,17-22,32-33,35H,6,8,10,12H2,1-5H3/t15?,17-,18+,19-,20-,21+,22-,24+,25-,26+,27-,28+,29-/m0/s1
InChIKey NVAICDOAKPCBRQ-WXPMOEDISA-N
Formula C29H36O11
HBA 11
HBD 3
MW 560.6
Rotatable Bonds 4
TPSA 161.96
LogP 1.43
Number Rings 7
Number Aromatic Rings 1
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.76
Exact Mass 560.23
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Khaya senegalensis Meliaceae Plantae 587579

Showing of synonyms

  • Nakatani M, Abdelgaleil SA, et al. (2001). Antifeedant rings B and D opened limonoids from Khaya senegalensis. Journal of Natural Products,2001,64(10),1261-1265. [View] [PubMed]
Pubchem: 101076684

No compound-protein relationship available.

Structure

SMILES: c1occc1C(OC(=O)C2)C3CCC4C(C5C6C4C237)CC(C5)CC6O7

Level: 1

Mol. Weight: 560.6 g/mol

Structure

SMILES: O1C2CC(C3)CC(C3C2C4C156)C4CCC5COC(=O)C6

Level: 0

Mol. Weight: 560.6 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 560.6 g/mol

Antifeedant
Antiviral

Absorption

Caco-2 (logPapp)
-5.65
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.830
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1.16

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.550
Plasma Protein Binding
82.78
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
3.540
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.810
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.250
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.920
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-5061.440
Rat (Acute)
5.030
Rat (Chronic Oral)
3.260
Fathead Minnow
14.350
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
387.670
Hydration Free Energy
-2.910
Log(D) at pH=7.4
1.740
Log(P)
1.36
Log S
-3.62
Log(Vapor Pressure)
-10.03
Melting Point
250.5
pKa Acid
5.9
pKa Basic
3.9
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7627
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7627
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7375
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7375
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7254
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7254
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7172
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7172

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