1alpha-acetoxy-5beta-hydroxyeudesm-3-en-6beta,11betaH-12,6-olide - Compound Card

1alpha-acetoxy-5beta-hydroxyeudesm-3-en-6beta,11betaH-12,6-olide

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1alpha-acetoxy-5beta-hydroxyeudesm-3-en-6beta,11betaH-12,6-olide

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@H]1CC=C([C@@]2([C@@]1(C)CC[C@@H]1[C@@H]2OC(=O)[C@H]1C)O)C
InChI InChI=1S/C17H24O5/c1-9-5-6-13(21-11(3)18)16(4)8-7-12-10(2)15(19)22-14(12)17(9,16)20/h5,10,12-14,20H,6-8H2,1-4H3/t10-,12-,13-,14-,16-,17+/m0/s1
InChIKey YNIPIBVFVRXGEW-CKQPZERJSA-N
Formula C17H24O5
HBA 5
HBD 1
MW 308.37
Rotatable Bonds 1
TPSA 72.83
LogP 1.98
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.76
Exact Mass 308.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia hugueti Asteraceae-Compositae Plantae 4219

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones from North African Artemisia species.. Phytochemistry,1994,37(2),477-485. [View]
Pubchem: 162943259

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 192.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.61
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.64
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.46
Plasma Protein Binding
46.55
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
10.97
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.09
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.37
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.2
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
-1.34
Rat (Acute)
2.58
Rat (Chronic Oral)
1.83
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
339.31
Hydration Free Energy
-6.24
Log(D) at pH=7.4
0.97
Log(P)
2.1
Log S
-2.89
Log(Vapor Pressure)
-6.49
Melting Point
155.66
pKa Acid
9.52
pKa Basic
5.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8470
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8470
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7522
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7522
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7146
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7146
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7009
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7009

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