Jaeschkeanadiol benzoate - Compound Card

Jaeschkeanadiol benzoate

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Jaeschkeanadiol benzoate

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CC1=CC[C@@]2([C@@H]([C@H](C1)OC(=O)c1ccccc1)[C@](CC2)(O)C(C)C)C
InChI InChI=1S/C22H30O3/c1-15(2)22(24)13-12-21(4)11-10-16(3)14-18(19(21)22)25-20(23)17-8-6-5-7-9-17/h5-10,15,18-19,24H,11-14H2,1-4H3/t18-,19+,21-,22+/m0/s1
InChIKey YOLDXKHOBUWSGX-YUVXSKOASA-N
Formula C22H30O3
HBA 3
HBD 1
MW 342.48
Rotatable Bonds 3
TPSA 46.53
LogP 4.76
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 342.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ferula sinaica Apiaceae Plantae 1514050
2 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]
  • Ahmed AA (1990). New Sesquiterpenes from Ferula sinaica. Journal of Natural Products,1990,53(2),483-486. [View] [PubMed]
Pubchem: 10125942

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC2CC=CCC(C23)CCC3

Level: 1

Mol. Weight: 342.48 g/mol

Structure

SMILES: C1CCC(C12)CCC=CC2

Level: 0

Mol. Weight: 342.48 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 342.48 g/mol

Antibacterial
Radical scavenging

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.4
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.8

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.7
Plasma Protein Binding
83.7
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
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.29
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.16
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.75
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.89
Micronucleos
Safe
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
Safe
T. Pyriformis
-1.08
Rat (Acute)
3.09
Rat (Chronic Oral)
1.93
Fathead Minnow
3.95
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
373.44
Hydration Free Energy
-5.72
Log(D) at pH=7.4
4.28
Log(P)
5.69
Log S
-5.27
Log(Vapor Pressure)
-6.04
Melting Point
117.28
pKa Acid
9.09
pKa Basic
5.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7819
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7819
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7753
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7753
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7450
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7450
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7420
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7420
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7092
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7092
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7019
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7019

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