1beta-angeloyloxy-9alpha-hydroxyeudesm-3,11(13)-dien-5alpha,7alphaH-12,6-olide - Compound Card

1beta-angeloyloxy-9alpha-hydroxyeudesm-3,11(13)-dien-5alpha,7alphaH-12,6-olide

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1beta-angeloyloxy-9alpha-hydroxyeudesm-3,11(13)-dien-5alpha,7alphaH-12,6-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C=C(\C(=O)O[C@@H]1CC=C([C@H]2[C@@]1(C)[C@H](O)C[C@@H]1[C@@H]2OC(=O)C1=C)C)/C
InChI InChI=1S/C20H26O5/c1-6-10(2)18(22)24-15-8-7-11(3)16-17-13(12(4)19(23)25-17)9-14(21)20(15,16)5/h6-7,13-17,21H,4,8-9H2,1-3,5H3/b10-6-/t13-,14+,15+,16+,17-,20-/m0/s1
InChIKey UUFLRDLXVUZQGL-KMJRVMNLSA-N
Formula C20H26O5
HBA 5
HBD 1
MW 346.42
Rotatable Bonds 2
TPSA 72.83
LogP 2.7
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 346.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pluchea dioscoridis Asteraceae Plantae —

Showing of synonyms

  • Mahmoud AA (1997). 7-Epi-eudesmanes, eudesmanoic acids, eudesmanolides and other sesquiterpenenes from Pluchea dioscoridis. Phytochemistry,1997,45(8),1633-1638. [View]
Pubchem: 163003466
Nmrshiftdb2: 60045864

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 346.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.59
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.65
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.62

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.61
Plasma Protein Binding
60.69
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.15
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.1
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.92
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.34
Micronucleos
Safe
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
-3.97
Rat (Acute)
3.61
Rat (Chronic Oral)
1.9
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
367.48
Hydration Free Energy
-5.63
Log(D) at pH=7.4
2.54
Log(P)
3.42
Log S
-3.64
Log(Vapor Pressure)
-7.16
Melting Point
140.94
pKa Acid
9.05
pKa Basic
4.88
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7972
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7972
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7582
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7582
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7165
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7165
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7069
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7069

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