2,3-epoxy-jaeschkeanadiol p-hydroxybenzoate - Compound Card

2,3-epoxy-jaeschkeanadiol p-hydroxybenzoate

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2,3-epoxy-jaeschkeanadiol p-hydroxybenzoate

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles Oc1ccc(cc1)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/C22H30O5/c1-13(2)22(25)10-9-20(3)12-17-21(4,27-17)11-16(18(20)22)26-19(24)14-5-7-15(23)8-6-14/h5-8,13,16-18,23,25H,9-12H2,1-4H3/t16-,17-,18+,20-,21+,22+/m0/s1
InChIKey NZRACXOBLXBSFK-QPOFKBRPSA-N
Formula C22H30O5
HBA 5
HBD 2
MW 374.48
Rotatable Bonds 3
TPSA 79.29
LogP 3.67
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 374.21
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, Hegazy MEF, et al. (2007). Ferulsinaic acid, a sesquiterpene coumarin with a rare carbon skeleton from Ferula species. Phytochemistry,2007,68(5),680-686. [View]
Pubchem: 91747168

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 374.48 g/mol

Structure

SMILES: C12C(O2)CCC3C(C1)CCC3

Level: 0

Mol. Weight: 374.48 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 374.48 g/mol

Radical scavenging

Absorption

Caco-2 (logPapp)
-5.02
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.560
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.320
Plasma Protein Binding
52.86
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
Non-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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
17.080
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.790
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.700
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.200
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
-6.570
Rat (Acute)
3.200
Rat (Chronic Oral)
2.080
Fathead Minnow
4.000
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
402.460
Hydration Free Energy
-5.640
Log(D) at pH=7.4
3.390
Log(P)
4.06
Log S
-4.37
Log(Vapor Pressure)
-6.86
Melting Point
159.75
pKa Acid
5.67
pKa Basic
4.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8208
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8208
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8045
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8045
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7763
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7763
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7669
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7669
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7555
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7555
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7501
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7501
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7425
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7425
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7345
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7345
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7315
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7315
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7121
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7121
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7019
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7019

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