1beta,9alpha-diacetyloxy-6beta-isobutoyloxy-4alpha-hydroxy-eudesm-11(13)-en-5alpha,7alpha,8alpha,12-olide - Compound Card

1beta,9alpha-diacetyloxy-6beta-isobutoyloxy-4alpha-hydroxy-eudesm-11(13)-en-5alpha,7alpha,8alpha,12-olide

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1beta,9alpha-diacetyloxy-6beta-isobutoyloxy-4alpha-hydroxy-eudesm-11(13)-en-5alpha,7alpha,8alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@@H]1[C@@H]2OC(=O)C(=C)[C@@H]2[C@H]([C@@H]2[C@]1(C)[C@H](O)CC[C@@]2(C)OC(=O)C)OC(=O)C(C)C
InChI InChI=1S/C23H32O9/c1-10(2)20(27)30-16-15-11(3)21(28)31-17(15)19(29-12(4)24)23(7)14(26)8-9-22(6,18(16)23)32-13(5)25/h10,14-19,26H,3,8-9H2,1-2,4-7H3/t14-,15-,16-,17-,18+,19-,22-,23+/m1/s1
InChIKey GRIBWILMVAKIDV-ZVSMCMQZSA-N
Formula C23H32O9
HBA 9
HBD 1
MW 452.5
Rotatable Bonds 4
TPSA 125.43
LogP 1.7
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.74
Exact Mass 452.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Wedelia prostrata Asteraceae Plantae 318064

Showing of synonyms

  • Farag SF, El-Emary NA, et al. (1996). Eudesmanolides from Wedelia prostrata. Chemical and Pharmaceutical Bulletin,1996,44(4),661-664. [View]
Pubchem: 162847161
Nmrshiftdb2: 70040337

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CC3C(C2)CCCC3

Level: 0

Mol. Weight: 452.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.66
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.74

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.34
Plasma Protein Binding
70.79
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.21
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.27
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.79
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.06
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
-33.9
Rat (Acute)
4.4
Rat (Chronic Oral)
2.05
Fathead Minnow
3.93
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
397.52
Hydration Free Energy
-3.65
Log(D) at pH=7.4
1.36
Log(P)
2.14
Log S
-3.94
Log(Vapor Pressure)
-8.26
Melting Point
151.77
pKa Acid
7.93
pKa Basic
2.51
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7078
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7078
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7027
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7027

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