3-oxo-4alpha-acetoxy-15-hydroxy-1alphaH,5alphaH,6betaH,7alphaH,11betaH-guai-10(14)-ene-6,12-olide - Compound Card

3-oxo-4alpha-acetoxy-15-hydroxy-1alphaH,5alphaH,6betaH,7alphaH,11betaH-guai-10(14)-ene-6,12-olide

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3-oxo-4alpha-acetoxy-15-hydroxy-1alphaH,5alphaH,6betaH,7alphaH,11betaH-guai-10(14)-ene-6,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC[C@@]1(OC(=O)C)C(=O)C[C@@H]2[C@H]1[C@H]1OC(=O)[C@H]([C@@H]1CCC2=C)C
InChI InChI=1S/C17H22O6/c1-8-4-5-11-9(2)16(21)22-15(11)14-12(8)6-13(20)17(14,7-18)23-10(3)19/h9,11-12,14-15,18H,1,4-7H2,2-3H3/t9-,11-,12-,14-,15-,17+/m0/s1
InChIKey BYTQBLSQDIOEOZ-QENAKCEXSA-N
Formula C17H22O6
HBA 6
HBD 1
MW 322.36
Rotatable Bonds 2
TPSA 89.9
LogP 1.01
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 322.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea musimomum Asteraceae Plantae 41503

Showing of synonyms

  • Medjroubi K, Benayache F, et al. (1997). Guaianolides from Centaurea musimomum. Phytochemistry,1997,5(7),1449-1451. [View]
Pubchem: 101713117
Nmrshiftdb2: 60048808

No compound-protein relationship available.

Structure

SMILES: C1C(=O)CC2C(=C)CCC(C3C12)CC(=O)O3

Level: 0

Mol. Weight: 322.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.49
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
-2.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.51
Plasma Protein Binding
50.66
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
8.25
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.46
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
Safe
Daphnia Maga
4.61
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
-1.82
Rat (Acute)
3.28
Rat (Chronic Oral)
2.05
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
366.65
Hydration Free Energy
-7.95
Log(D) at pH=7.4
0.43
Log(P)
0.88
Log S
-2.31
Log(Vapor Pressure)
-7.13
Melting Point
168.52
pKa Acid
7.32
pKa Basic
5.06
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8067
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8067
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7915
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7915
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7655
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7655
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7184
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7184
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7162
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7162

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