Khayanolide D - Compound Card

Khayanolide D

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Khayanolide D

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles COC(=O)C[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)O
InChI InChI=1S/C27H34O9/c1-22-12-25(31)19-18(20(22)30)36-26-10-17(29)35-21(13-6-8-34-11-13)23(26,2)7-5-14(27(19,26)32)24(25,3)15(22)9-16(28)33-4/h6,8,11,14-15,18-21,30-32H,5,7,9-10,12H2,1-4H3/t14?,15-,18+,19-,20+,21-,22+,23-,24+,25-,26+,27-/m0/s1
InChIKey LVKULLURUFYYEU-WSAROZLISA-N
Formula C27H34O9
HBA 9
HBD 3
MW 502.56
Rotatable Bonds 3
TPSA 135.66
LogP 1.88
Number Rings 7
Number Aromatic Rings 1
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 502.22
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Khaya senegalensis Meliaceae Plantae 587579

Showing of synonyms

  • Nakatani M, Abdelgaleil SA, et al. (2002). Three new modified limonoids from Khaya senegalensis. Journal of Natural Products,2002,65(8),1219-1221. [View] [PubMed]
Pubchem: 101195134

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 502.56 g/mol

Structure

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

Level: 0

Mol. Weight: 502.56 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 502.56 g/mol

Antifeedant

Absorption

Caco-2 (logPapp)
-5.53
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.880
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.79

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.600
Plasma Protein Binding
79.21
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.670
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.450
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.650
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.500
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
-886.740
Rat (Acute)
5.070
Rat (Chronic Oral)
2.930
Fathead Minnow
2.950
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
457.970
Hydration Free Energy
-2.890
Log(D) at pH=7.4
2.070
Log(P)
1.84
Log S
-3.69
Log(Vapor Pressure)
-10.63
Melting Point
239.37
pKa Acid
5.97
pKa Basic
4.95
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 0.7929
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7929
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7363
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7363
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7105
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7105

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