4alpha,10beta-dihydroxy-2-oxo-guaia-1(5)-en-6alpha,12-olide - Compound Card

4alpha,10beta-dihydroxy-2-oxo-guaia-1(5)-en-6alpha,12-olide

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4alpha,10beta-dihydroxy-2-oxo-guaia-1(5)-en-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C[C@@H]1C(=O)O[C@H]2[C@H]1CC[C@](C1=C2[C@](C)(O)CC1=O)(C)O
InChI InChI=1S/C15H20O5/c1-7-8-4-5-14(2,18)10-9(16)6-15(3,19)11(10)12(8)20-13(7)17/h7-8,12,18-19H,4-6H2,1-3H3/t7-,8-,12-,14-,15+/m0/s1
InChIKey ZSOYDVICJGNUTP-CMFXOGKPSA-N
Formula C15H20O5
HBA 5
HBD 2
MW 280.32
Rotatable Bonds 0
TPSA 83.83
LogP 0.73
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 Artemisia argentea Asteraceae Plantae 669119

Showing of synonyms

  • El-Emary NA, Makboul MA, et al. (1987). Sesquiterpene lactones from Artemisia argentea.. Phytochemistry,1987,26(1),314-315. [View]
Pubchem: 101593133
Chebi: 174668
Nmrshiftdb2: 70003733

No compound-protein relationship available.

Structure

SMILES: O=C1CCC(=C12)C3C(CC(=O)O3)CCC2

Level: 0

Mol. Weight: 280.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.59
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.86

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.44
Plasma Protein Binding
38.35
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
6.62
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.75
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.25
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.73
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
-2.41
Rat (Acute)
2.51
Rat (Chronic Oral)
1.9
Fathead Minnow
3.62
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
349.47
Hydration Free Energy
-9.66
Log(D) at pH=7.4
0.44
Log(P)
-0.14
Log S
-1.27
Log(Vapor Pressure)
-6.19
Melting Point
179.72
pKa Acid
6.9
pKa Basic
5.12
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.8363
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.8363
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7922
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7922
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 5 0.7586
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 5 0.7586
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 5 0.7447
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 5 0.7447
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7256
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7256

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