1beta,9beta-diacetoxyeudesm-3-en-5alpha,6beta,11beta-H-12,6-olide - Compound Card

1beta,9beta-diacetoxyeudesm-3-en-5alpha,6beta,11beta-H-12,6-olide

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1beta,9beta-diacetoxyeudesm-3-en-5alpha,6beta,11beta-H-12,6-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@H]1C[C@H]2[C@H](C)C(=O)O[C@@H]2[C@@H]2[C@]1(C)[C@@H](CC=C2C)OC(=O)C
InChI InChI=1S/C19H26O6/c1-9-6-7-14(23-11(3)20)19(5)15(24-12(4)21)8-13-10(2)18(22)25-17(13)16(9)19/h6,10,13-17H,7-8H2,1-5H3/t10-,13-,14+,15-,16+,17-,19+/m0/s1
InChIKey KCTHTUFPZVGRQO-GZVTUANZSA-N
Formula C19H26O6
HBA 6
HBD 0
MW 350.41
Rotatable Bonds 2
TPSA 78.9
LogP 2.4
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.74
Exact Mass 350.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia herba-alba Asteraceae Plantae 72329
2 Artemisia herba-alba Asteraceae Plantae 72329

Showing of synonyms

  • Laid M (2011). Etude phytochimique d’une plante médicinale de l’Est Algérien (Artemisia herba alba).. PhD Thesis, 2011, Universite Mantouri-Constantine, Faculty of Science, Algeria. [View]
  • Laid M, Hegazy MEF, et al. (2008). Sesquiterpene lactones from Algerian Artemisia herba-alba.. Phytochemistry Letters,2008,1,85-88. [View]
Pubchem: 162817360

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C12)C3C(CC2)CCC=C3

Level: 0

Mol. Weight: 350.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.61
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.67
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.31

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
53.63
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
12.66
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.31
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.28
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.47
Micronucleos
Safe
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
-3.35
Rat (Acute)
3.04
Rat (Chronic Oral)
1.97
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
368.02
Hydration Free Energy
-5.65
Log(D) at pH=7.4
1.33
Log(P)
2.33
Log S
-3.5
Log(Vapor Pressure)
-6.78
Melting Point
141.41
pKa Acid
10.41
pKa Basic
5.03
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8132
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8132
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7453
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7453
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7308
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7308

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