Empetrifranzinan B - Compound Card

Empetrifranzinan B

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Empetrifranzinan B

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CC(C(=O)c1c(O)cc2c3c1OC1(C)CCC(C3C1)C(O2)(C)C)C
InChI InChI=1S/C20H26O4/c1-10(2)17(22)16-13(21)8-14-15-11-9-20(5,24-18(15)16)7-6-12(11)19(3,4)23-14/h8,10-12,21H,6-7,9H2,1-5H3
InChIKey COMRWAQJXJEENM-UHFFFAOYSA-N
Formula C20H26O4
HBA 4
HBD 1
MW 330.42
Rotatable Bonds 2
TPSA 55.76
LogP 4.44
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 330.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hypericum roeperianum Hypericaceae Plantae —

Showing of synonyms

  • Fobofou SA, Franke K, et al. (2015). Isolation and anticancer, anthelminthic, and antiviral (HIV) activity of acylphloroglucinols, and regioselective synthesis of empetrifranzinans from Hypericum roeperianum.. Bioorganic & medicinal chemistry,2015, 23(19), 6327-6334. [View] [PubMed]
Pubchem: 71495029
Nmrshiftdb2: 70029723

No compound-protein relationship available.

Structure

SMILES: c12c3cccc1OCC4C2CC(O3)CC4

Level: 0

Mol. Weight: 330.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.54
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.91
Plasma Protein Binding
43.3
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.55
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.66
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.96
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.78
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
Toxic
T. Pyriformis
3.48
Rat (Acute)
2.59
Rat (Chronic Oral)
1.9
Fathead Minnow
4.32
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
372.05
Hydration Free Energy
-6.29
Log(D) at pH=7.4
3.99
Log(P)
5.54
Log S
-5.59
Log(Vapor Pressure)
-6.04
Melting Point
136.76
pKa Acid
8.04
pKa Basic
4.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7890
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7844
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7841
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7456
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7317
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7275
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7192
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7103

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