Limonin diosphenol - Compound Card

Limonin diosphenol

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Limonin diosphenol

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles O=C1OC[C@]23[C@H](C1)OC(C2=C(O)C(=O)[C@@]1([C@@H]3CC[C@@]2([C@]31O[C@@H]3C(=O)O[C@@H]2c1cocc1)C)C)(C)C
InChI InChI=1S/C26H28O9/c1-22(2)17-16(28)18(29)24(4)13(25(17)11-32-15(27)9-14(25)34-22)5-7-23(3)19(12-6-8-31-10-12)33-21(30)20-26(23,24)35-20/h6,8,10,13-14,19-20,28H,5,7,9,11H2,1-4H3/t13-,14-,19+,20+,23-,24-,25-,26+/m0/s1
InChIKey SNGHLUWTFLYPMT-SFHGJMHFSA-N
Formula C26H28O9
HBA 9
HBD 1
MW 484.5
Rotatable Bonds 1
TPSA 124.8
LogP 2.94
Number Rings 7
Number Aromatic Rings 1
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 484.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Calodendrum capense Rutaceae Plantae 68533

Showing of synonyms

  • Kiprop AK, Rajab MS, et al. (2005). Isolation and characterization of larvicidal components against mosquito larvae (Aedes aegypti Linn.) from Calodendrum capense Thunb. Bulletin of the Chemical Society of Ethiopia,2005,19(1),145-148. [View] [PubMed]
Pubchem: 44575802
Nmrshiftdb2: 60075029

No compound-protein relationship available.

Structure

SMILES: c1occc1C(OC(=O)C(C234)O4)C3CCC5C67C(=CC(=O)C25)COC6CC(=O)OC7

Level: 1

Mol. Weight: 484.5 g/mol

Structure

SMILES: C123C(O3)C(=O)OCC2CCC4C56C(=CC(=O)C14)COC5CC(=O)OC6

Level: 0

Mol. Weight: 484.5 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 484.5 g/mol

Larvicidal

Absorption

Caco-2 (logPapp)
-5.25
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.94
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.91

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
44.9
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
10.84
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.18
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.26
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.6
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
-544.91
Rat (Acute)
5.63
Rat (Chronic Oral)
2.09
Fathead Minnow
4.02
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
495.62
Hydration Free Energy
-2.92
Log(D) at pH=7.4
1.54
Log(P)
1.34
Log S
-4.96
Log(Vapor Pressure)
-9.75
Melting Point
307.67
pKa Acid
3.72
pKa Basic
3.58
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7711
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7711
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7265
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7265
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7173
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7173
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7169
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7169
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7167
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7167
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7018
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7018
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7013
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7013

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