3beta-acetoxy-1beta,4alpha,13-trihydroxyeudesm-7(11)-en-6alpha,12-olide - Compound Card

3beta-acetoxy-1beta,4alpha,13-trihydroxyeudesm-7(11)-en-6alpha,12-olide

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3beta-acetoxy-1beta,4alpha,13-trihydroxyeudesm-7(11)-en-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)OCC1=C2CCC3[C@@H]([C@H]2OC1=O)[C@](C)(O)[C@H](C[C@H]3O)OC(=O)C
InChI InChI=1S/C18H24O8/c1-8(19)24-7-12-10-4-5-11-13(21)6-14(25-9(2)20)18(3,23)15(11)16(10)26-17(12)22/h11,13-16,21,23H,4-7H2,1-3H3/t11?,13-,14+,15+,16+,18-/m1/s1
InChIKey BVUOEMQPQZHKOS-BKKHBGKHSA-N
Formula C18H24O8
HBA 8
HBD 2
MW 368.38
Rotatable Bonds 3
TPSA 119.36
LogP 0.24
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.72
Exact Mass 368.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Achillea fragrantissima Asteraceae Plantae 282738

Showing of synonyms

  • Abdel-Mogib M, Jakupovic J, et al. (1989). Glaucolides from Achillea fragrantissima.. Phytochemistry,1989,28(12),3528-3530. [View]
Pubchem: 163009019

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C=12)C3C(CC2)CCCC3

Level: 0

Mol. Weight: 368.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.75
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.31
Plasma Protein Binding
35.65
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
7.18
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.44
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.31
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.15
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
-2.97
Rat (Acute)
3.6
Rat (Chronic Oral)
1.97
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
382.78
Hydration Free Energy
-8.56
Log(D) at pH=7.4
0.44
Log(P)
0.74
Log S
-2.25
Log(Vapor Pressure)
-7.81
Melting Point
159.51
pKa Acid
7.98
pKa Basic
4.23
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7719
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7719
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7631
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7631
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7339
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7339
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7263
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7263

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