2,3-epoxy-jaeschkeanadiol benzoate - Compound Card

2,3-epoxy-jaeschkeanadiol benzoate

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2,3-epoxy-jaeschkeanadiol benzoate

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Daucane Sesquiterpenoid Ester
Canonical Smiles O=C(c1ccccc1)O[C@H]1C[C@@]2(C)O[C@H]2C[C@@]2([C@@H]1[C@@](O)(CC2)C(C)C)C
InChI InChI=1S/C22H30O4/c1-14(2)22(24)11-10-20(3)13-17-21(4,26-17)12-16(18(20)22)25-19(23)15-8-6-5-7-9-15/h5-9,14,16-18,24H,10-13H2,1-4H3/t16-,17-,18+,20+,21+,22+/m0/s1
InChIKey KCLKOOIYAAERJD-IVDWBNGSSA-N
Formula C22H30O4
HBA 4
HBD 1
MW 358.48
Rotatable Bonds 3
TPSA 59.06
LogP 3.97
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 358.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ferula hermonis Apiaceae Plantae 662815

Showing of synonyms

  • Ibraheim ZZ, Abdel-Mageed WM, et al. (2012). Antimicrobial antioxidant daucane sesquiterpenes from Ferula hermonis Boiss. Phytotherapy Research,2012,26,579-586. [View] [PubMed]
Pubchem: 10309067
Nmrshiftdb2: 70038187

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC(CC(O2)C23)C4C(C3)CCC4

Level: 1

Mol. Weight: 358.48 g/mol

Structure

SMILES: C12C(O2)CCC3C(C1)CCC3

Level: 0

Mol. Weight: 358.48 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 358.48 g/mol

Radical scavenging

Absorption

Caco-2 (logPapp)
-4.91
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.44
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.4
Plasma Protein Binding
56.39
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
15.99
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.1
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.84
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.88
Micronucleos
Safe
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
Toxic
T. Pyriformis
-5.2
Rat (Acute)
3.38
Rat (Chronic Oral)
1.93
Fathead Minnow
3.97
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
397.15
Hydration Free Energy
-4.83
Log(D) at pH=7.4
3.7
Log(P)
4.32
Log S
-4.59
Log(Vapor Pressure)
-6.18
Melting Point
109.0
pKa Acid
6.05
pKa Basic
4.41
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7442
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7442
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7019
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7019

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