1-O-acetylkhayanolide A - Compound Card

1-O-acetylkhayanolide A

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1-O-acetylkhayanolide A

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)[C@H]1CC[C@@]4([C@]5([C@]1([C@@H]3C(=O)[C@H]2O)O5)CC(=O)O[C@H]4c1cocc1)C)OC(=O)C)O
InChI InChI=1S/C29H34O11/c1-13(30)39-27-12-24(2)19(18(33)23(35)36-5)26(27,4)15-6-8-25(3)22(14-7-9-37-11-14)38-16(31)10-28(25)29(15,40-28)20(27)17(32)21(24)34/h7,9,11,15,18-22,33-34H,6,8,10,12H2,1-5H3/t15-,18+,19+,20-,21-,22+,24-,25+,26-,27+,28+,29+/m1/s1
InChIKey OQWXSIPGIIEHTO-WKUHGQEESA-N
Formula C29H34O11
HBA 11
HBD 2
MW 558.58
Rotatable Bonds 4
TPSA 162.1
LogP 1.63
Number Rings 7
Number Aromatic Rings 1
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.72
Exact Mass 558.21
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: 102019660

No compound-protein relationship available.

Structure

SMILES: c1occc1C(OC(=O)C2)C(C2(C345)O5)CCC4C6C7C3C(=O)CC(C7)C6

Level: 1

Mol. Weight: 558.58 g/mol

Structure

SMILES: C1C(=O)OCC(C1(C234)O4)CCC3C5C6C2C(=O)CC(C6)C5

Level: 0

Mol. Weight: 558.58 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 558.58 g/mol

Antifeedant
Antiviral

Absorption

Caco-2 (logPapp)
-5.15
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.760
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.55

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.170
Plasma Protein Binding
62.6
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.570
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.400
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.100
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
7.540
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
-3889.070
Rat (Acute)
5.580
Rat (Chronic Oral)
2.860
Fathead Minnow
12.160
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
422.970
Hydration Free Energy
-2.860
Log(D) at pH=7.4
1.160
Log(P)
1.02
Log S
-4.35
Log(Vapor Pressure)
-9.88
Melting Point
262.08
pKa Acid
3.88
pKa Basic
2.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9156
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9156
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8182
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8182
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8101
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8101
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8062
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8062
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8017
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8017
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7998
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7998
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7900
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7900
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7651
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7651
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7606
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7606
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7490
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7490
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7389
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7389
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7220
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7220
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7138
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7138
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7073
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7073
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7032
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7032
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7008
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7008

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