2,3-epoxy-jaeschkeanadiol vanillate - Compound Card

2,3-epoxy-jaeschkeanadiol vanillate

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2,3-epoxy-jaeschkeanadiol vanillate

Structure
Zoomed Structure
  • Family: Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Daucane Sesquiterpenoid Ester
Canonical Smiles COc1cc(ccc1O)C(=O)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/C23H32O6/c1-13(2)23(26)9-8-21(3)12-18-22(4,29-18)11-17(19(21)23)28-20(25)14-6-7-15(24)16(10-14)27-5/h6-7,10,13,17-19,24,26H,8-9,11-12H2,1-5H3/t17-,18-,19+,21+,22+,23+/m0/s1
InChIKey LUXHNMNHDPKHBY-CNAOLAIUSA-N
Formula C23H32O6
HBA 6
HBD 2
MW 404.5
Rotatable Bonds 4
TPSA 88.52
LogP 3.68
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 404.22
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: 13992122

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 272.34 g/mol

Structure

SMILES: C12C(O2)CCC3C(C1)CCC3

Level: 0

Mol. Weight: 152.24 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Radical scavenging

Absorption

Caco-2 (logPapp)
-5.08
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.640
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.420
Plasma Protein Binding
54.31
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
18.060
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.900
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.690
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.610
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-16.380
Rat (Acute)
3.150
Rat (Chronic Oral)
2.130
Fathead Minnow
4.020
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
420.040
Hydration Free Energy
-5.190
Log(D) at pH=7.4
3.220
Log(P)
3.81
Log S
-4.49
Log(Vapor Pressure)
-7.09
Melting Point
149.01
pKa Acid
6.03
pKa Basic
4.12
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8747
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8747
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8520
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8520
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7874
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7874
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7599
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7599
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7547
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7547
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7264
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7264
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7226
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7226
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7173
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7173
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7165
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7165
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7152
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7152
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7107
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7107

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