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

6beta-isobutoyloxy-1beta,4alpha-dihydroxy-9-alpha-tigloyloxyeudesm-11(13)-en-5alpha,7alpha,8alpha,12-olide

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6beta-isobutoyloxy-1beta,4alpha-dihydroxy-9-alpha-tigloyloxyeudesm-11(13)-en-5alpha,7alpha,8alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C=C(/C(=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)O)OC(=O)C(C)C)\C
InChI InChI=1S/C24H34O8/c1-8-12(4)21(27)32-19-17-15(13(5)22(28)31-17)16(30-20(26)11(2)3)18-23(6,29)10-9-14(25)24(18,19)7/h8,11,14-19,25,29H,5,9-10H2,1-4,6-7H3/b12-8+/t14-,15-,16-,17-,18+,19-,23-,24+/m1/s1
InChIKey RDXQYZATVQTRST-VJTLMBDDSA-N
Formula C24H34O8
HBA 8
HBD 2
MW 450.53
Rotatable Bonds 4
TPSA 119.36
LogP 2.07
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 450.23
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: 10321521
Nmrshiftdb2: 70040341

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 450.53 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.6
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.7
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.55

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.43
Plasma Protein Binding
79.87
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
7.15
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.63
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.42
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
-37.28
Rat (Acute)
4.17
Rat (Chronic Oral)
2.21
Fathead Minnow
4.01
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
397.11
Hydration Free Energy
-3.13
Log(D) at pH=7.4
2.08
Log(P)
2.78
Log S
-3.92
Log(Vapor Pressure)
-8.34
Melting Point
159.29
pKa Acid
7.46
pKa Basic
3.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7854
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7854
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7569
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7569
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7567
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7567
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7205
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7205

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