15-hydroxy-4beta,15,11beta,13-tetrahydroreynosin - Compound Card

15-hydroxy-4beta,15,11beta,13-tetrahydroreynosin

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15-hydroxy-4beta,15,11beta,13-tetrahydroreynosin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC[C@@H]1CC[C@H]([C@]2([C@H]1[C@H]1OC(=O)C(=C)C1CC2)C)O
InChI InChI=1S/C15H22O4/c1-8-10-5-6-15(2)11(17)4-3-9(7-16)12(15)13(10)19-14(8)18/h9-13,16-17H,1,3-7H2,2H3/t9-,10?,11+,12+,13-,15-/m0/s1
InChIKey TZPNSKUJWADAOC-XJQHZFAKSA-N
Formula C15H22O4
HBA 4
HBD 2
MW 266.34
Rotatable Bonds 1
TPSA 66.76
LogP 1.26
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 266.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sonchus macrocarpus Asteraceae Plantae 2984305

Showing of synonyms

  • Mahmoud Z, El-Masry S, et al. (1984). Sesquiterpene lactones from Sonchus macrocarpus. Phytochemistry,1984,23(5),1105-1107. [View]
Pubchem: 162988896

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)C3C(CC2)CCCC3

Level: 0

Mol. Weight: 266.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.460
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.580
Plasma Protein Binding
39.82
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
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-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
11.080
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.530
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.140
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.510
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
0.160
Rat (Acute)
2.420
Rat (Chronic Oral)
1.900
Fathead Minnow
3.800
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
371.750
Hydration Free Energy
-8.270
Log(D) at pH=7.4
0.930
Log(P)
0.26
Log S
-1.96
Log(Vapor Pressure)
-6.97
Melting Point
154.58
pKa Acid
9.42
pKa Basic
7.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7395
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7395
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7192
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7192
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7123
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7123
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7072
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7072
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7027
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7027

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