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

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

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3-oxo-4alpha-hydroxy-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(O)C(=O)C[C@@H]2[C@H]1[C@H]1OC(=O)[C@H]([C@@H]1CCC2=C)C
InChI InChI=1S/C15H20O5/c1-7-3-4-9-8(2)14(18)20-13(9)12-10(7)5-11(17)15(12,19)6-16/h8-10,12-13,16,19H,1,3-6H2,2H3/t8-,9-,10-,12-,13-,15+/m0/s1
InChIKey YXNSRUQZUQFDQO-HZTOAZILSA-N
Formula C15H20O5
HBA 5
HBD 2
MW 280.32
Rotatable Bonds 1
TPSA 83.83
LogP 0.44
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 280.13
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: 101713118
Nmrshiftdb2: 60048809

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 280.32 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
-2.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.52
Plasma Protein Binding
51.52
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.97
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.19
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.14
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.01
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
-0.82
Rat (Acute)
2.95
Rat (Chronic Oral)
2.19
Fathead Minnow
3.71
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
370.2
Hydration Free Energy
-10.68
Log(D) at pH=7.4
0.32
Log(P)
0.83
Log S
-1.76
Log(Vapor Pressure)
-7.97
Melting Point
185.39
pKa Acid
6.73
pKa Basic
6.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7347
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7347
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7171
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7171
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7043
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7043

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