1beta-hydroxy-3-oxo-eudesman-6alpha,12-olide - Compound Card

1beta-hydroxy-3-oxo-eudesman-6alpha,12-olide

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1beta-hydroxy-3-oxo-eudesman-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@@]1([C@@H]2[C@H](C)C(=O)C[C@H]1O)C
InChI InChI=1S/C15H22O4/c1-7-9-4-5-15(3)11(17)6-10(16)8(2)12(15)13(9)19-14(7)18/h7-9,11-13,17H,4-6H2,1-3H3/t7-,8+,9-,11+,12+,13-,15-/m0/s1
InChIKey YRFWEPYMRLGVBZ-SNNRJATNSA-N
Formula C15H22O4
HBA 4
HBD 1
MW 266.34
Rotatable Bonds 0
TPSA 63.6
LogP 1.55
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 266.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia arborescens Asteraceae Plantae 72386
2 Tanacetum sinaicum Asteraceae Plantae —

Showing of synonyms

  • Hegazy MEF, Hamed AR, et al. (2015). Anti-inflammatory sesquiterpenes from the medicinal herb Tanacetum sinaicum. RSC Advances,2015,5,44895-44901. [View]
  • Marco JA, Sanz-Cervera JF, et al. (1997). Sesquiterpene lactones and lignans from Artemisia arborescens.. Phytochemistry,1997,44(6),1133-1137. [View]
Pubchem: 13864723

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C12)C3C(CC2)CCC(=O)C3

Level: 0

Mol. Weight: 266.34 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.58
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.51
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.97

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.65
Plasma Protein Binding
49.18
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.19
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.57
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.19
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
3.97
Micronucleos
Safe
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
-0.35
Rat (Acute)
2.04
Rat (Chronic Oral)
1.77
Fathead Minnow
3.58
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
360.8
Hydration Free Energy
-7.43
Log(D) at pH=7.4
0.49
Log(P)
0.67
Log S
-1.91
Log(Vapor Pressure)
-6.34
Melting Point
187.22
pKa Acid
8.28
pKa Basic
6.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8616
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8616
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8139
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8139
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8139
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8139
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8023
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8023
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7841
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7841
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7631
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7631
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7592
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7592
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7438
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7438
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7382
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7382
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7356
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7356
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7178
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7178
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7084
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7084
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7077
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7077

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