8-acetoxyisochiliolide lactone - Compound Card

8-acetoxyisochiliolide lactone

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8-acetoxyisochiliolide lactone

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@@]1(C)CC[C@]2([C@]3([C@]41CC(OC4=O)c1ccoc1)CC[C@]2(C(=O)O3)C)C
InChI InChI=1S/C22H26O7/c1-13(23)28-20(4)8-7-19(3)18(2)6-9-22(19,29-16(18)24)21(20)11-15(27-17(21)25)14-5-10-26-12-14/h5,10,12,15H,6-9,11H2,1-4H3/t15?,18-,19+,20-,21+,22-/m0/s1
InChIKey DZWWDEZOKZIEMT-BACIYOGHSA-N
Formula C22H26O7
HBA 7
HBD 0
MW 402.44
Rotatable Bonds 2
TPSA 92.04
LogP 3.47
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 402.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Microglossa pyrifolia Asteraceae Plantae 1898725

Showing of synonyms

  • Akimanya A, Midiwo JO, et al. (2015). Two polymethoxylated flavonoids with antioxidant activities and a rearranged clerodane diterpenoid from the leaf exudates of Microglossa pyrifolia. Phytochemistry Letters,2015,11,183-187. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1occc1C(C2)OC(=O)C23C45C(C(C(=O)O5)CC4)CCC3

Level: 1

Mol. Weight: 402.44 g/mol

Structure

SMILES: C1COC(=O)C12C34C(C(C(=O)O4)CC3)CCC2

Level: 0

Mol. Weight: 402.44 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 402.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.93
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.79
Plasma Protein Binding
62.15
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
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
7.59
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.0
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.18
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.89
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
-25.89
Rat (Acute)
4.07
Rat (Chronic Oral)
1.88
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
405.1
Hydration Free Energy
-4.72
Log(D) at pH=7.4
2.24
Log(P)
2.26
Log S
-4.72
Log(Vapor Pressure)
-7.6
Melting Point
231.96
pKa Acid
7.89
pKa Basic
5.07
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8975
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8975
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8809
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8809
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7674
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7674
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 3 0.7064
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 3 0.7064
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7060
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7060

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