1alpha,3beta-dihydroxy-9beta,10beta-epoxy-7alpha,11betaH-germacra-4Z-en-12,6alpha-olide - Compound Card

1alpha,3beta-dihydroxy-9beta,10beta-epoxy-7alpha,11betaH-germacra-4Z-en-12,6alpha-olide

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1alpha,3beta-dihydroxy-9beta,10beta-epoxy-7alpha,11betaH-germacra-4Z-en-12,6alpha-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C1O[C@H]2[C@H]([C@@H]1C)C[C@@H]1O[C@]1(C)[C@H](C[C@@H](/C(=C\2)/C)O)O
InChI InChI=1S/C15H22O5/c1-7-4-11-9(8(2)14(18)19-11)5-13-15(3,20-13)12(17)6-10(7)16/h4,8-13,16-17H,5-6H2,1-3H3/b7-4-/t8-,9-,10-,11+,12-,13-,15+/m0/s1
InChIKey KJRZFQQUFIBFFI-LJNYLYBWSA-N
Formula C15H22O5
HBA 5
HBD 2
MW 282.34
Rotatable Bonds 0
TPSA 79.29
LogP 0.78
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 282.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pyrethrum santolinoides Asteraceae Plantae 2072400

Showing of synonyms

  • Abdel-Mogib M, Jakupovic J, et al. (1989). Sesquiterpene lactones from Pyrethrum santolinoides. Phytochemistry,1989,28(1),268-271. [View]
Pubchem: 14194094
Nmrshiftdb2: 60061837

No compound-protein relationship available.

Structure

SMILES: C12C(O2)CCCC=CC3C(C1)CC(=O)O3

Level: 0

Mol. Weight: 282.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.16
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.42
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.21
Plasma Protein Binding
19.1
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.28
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.16
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.11
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.97
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-2.19
Rat (Acute)
3.39
Rat (Chronic Oral)
2.02
Fathead Minnow
3.61
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
368.27
Hydration Free Energy
-10.14
Log(D) at pH=7.4
-0.49
Log(P)
0.2
Log S
-1.11
Log(Vapor Pressure)
-6.6
Melting Point
139.66
pKa Acid
6.32
pKa Basic
3.67
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7633
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7633
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7226
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7226
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7131
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7131

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