1beta,5beta-epoxy-11alpha,13-dihydrotomentosin - Compound Card

1beta,5beta-epoxy-11alpha,13-dihydrotomentosin

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1beta,5beta-epoxy-11alpha,13-dihydrotomentosin

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)/C=C/[C@]12O[C@@H]2C[C@H]2[C@@H](C[C@@H]1C)OC(=O)[C@H]2C
InChI InChI=1S/C15H20O4/c1-8-6-12-11(10(3)14(17)18-12)7-13-15(8,19-13)5-4-9(2)16/h4-5,8,10-13H,6-7H2,1-3H3/b5-4+/t8-,10-,11+,12+,13+,15-/m0/s1
InChIKey PNFGMIFHPGOUEO-MLZISUFGSA-N
Formula C15H20O4
HBA 4
HBD 0
MW 264.32
Rotatable Bonds 2
TPSA 55.9
LogP 1.88
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 264.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Xanthium pungens Asteraceae-Compositae Plantae 1979456

Showing of synonyms

  • Ahmed AA, Jakupovic J, et al. (1990). Sesquiterpene lactones from Xanthium pungens. Phytochemistry,1990,29(7),2211-2215. [View]
Pubchem: 102056125
Nmrshiftdb2: 60077462

No compound-protein relationship available.

Structure

SMILES: C12C(O2)CCC3C(C1)CC(=O)O3

Level: 0

Mol. Weight: 168.19 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.06
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.46
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.12
Plasma Protein Binding
26.34
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.89
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.75
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.13
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.31
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
0.52
Rat (Acute)
2.34
Rat (Chronic Oral)
1.67
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
351.4
Hydration Free Energy
-5.87
Log(D) at pH=7.4
0.99
Log(P)
0.81
Log S
-2.2
Log(Vapor Pressure)
-4.58
Melting Point
89.33
pKa Acid
6.9
pKa Basic
4.9
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8701
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8701
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8109
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8109
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7143
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7143
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7072
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7072

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