11beta,13-dihydrolactucin - Compound Card

11beta,13-dihydrolactucin

Select a section from the left sidebar

11beta,13-dihydrolactucin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCC1=CC(=O)C2=C(C)C[C@@H]([C@@H]3[C@@H]([C@@H]12)OC(=O)[C@H]3C)O
InChI InChI=1S/C15H18O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,7,9,12-14,16-17H,3,5H2,1-2H3/t7-,9-,12+,13-,14-/m0/s1
InChIKey ZHZZKRDEPZMPLJ-WLVQVHLUSA-N
Formula C15H18O5
HBA 5
HBD 2
MW 278.3
Rotatable Bonds 1
TPSA 83.83
LogP 0.36
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 278.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Launaea mucronata Asteraceae Plantae 1423391
2 Launaea arborescens Asteraceae Plantae 43199
3 Lactuca sativa Asteraceae Plantae 4236

Showing of synonyms

  • Sarg TM, Omar AA, et al. (1982). 11beta,13-dihydrolactucin, a sesquiterpene lactone from Launaea mucronata. Phytochemistry,1982,21(5),1163. [View]
  • Bitam F, Ciavatta ML, et al. (2008). Chemical characterisation of the terpenoid constituents of the Algerian plant Launaea arborescens. Phytochemistry,2008,69,2984-2992. [View] [PubMed]
  • Mahmoud ZF, Kassem FF, et al. (1986). Sesquiterpene lactones from Lactuca sativa. Phytochemistry,1986,25(3),141-748. [View]
Pubchem: 9970764
Chebi: 90267
Nmrshiftdb2: 70002286
Metabolights: MTBLC90267
CPRiL: 61025
Structure

SMILES: O=C1C=CC(C1=2)C3C(CC(=O)O3)CCC2

Level: 0

Mol. Weight: 278.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.47
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.4
Plasma Protein Binding
39.26
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
6.0
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.72
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.06
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.25
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
Safe
T. Pyriformis
-0.4
Rat (Acute)
3.16
Rat (Chronic Oral)
2.11
Fathead Minnow
3.9
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
375.79
Hydration Free Energy
-10.65
Log(D) at pH=7.4
-0.21
Log(P)
-0.01
Log S
-1.47
Log(Vapor Pressure)
-7.04
Melting Point
195.62
pKa Acid
7.26
pKa Basic
5.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8067
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8067
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7238
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7238

Download SDF