8alpha-angeloyloxy-1beta,10alpha-epoxy-2alpha-hydroxy-l5-oxo-germacr-11(13)-en-12,6alpha-olide - Compound Card

8alpha-angeloyloxy-1beta,10alpha-epoxy-2alpha-hydroxy-l5-oxo-germacr-11(13)-en-12,6alpha-olide

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8alpha-angeloyloxy-1beta,10alpha-epoxy-2alpha-hydroxy-l5-oxo-germacr-11(13)-en-12,6alpha-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=CC1C[C@H]2OC(=O)C(=C)[C@@H]2[C@@H](OC(=O)/C(=C\C)/C)C[C@@]2([C@@H]([C@H](C1)O)O2)C
InChI InChI=1S/C20H26O7/c1-5-10(2)18(23)26-15-8-20(4)17(27-20)13(22)6-12(9-21)7-14-16(15)11(3)19(24)25-14/h5,9,12-17,22H,3,6-8H2,1-2,4H3/b10-5-/t12?,13-,14+,15-,16-,17+,20+/m0/s1
InChIKey HGTSWZZRQSWMEQ-FOGAHLTCSA-N
Formula C20H26O7
HBA 7
HBD 1
MW 378.42
Rotatable Bonds 3
TPSA 102.43
LogP 1.48
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 378.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Gutenbergia cordifolia Asteraceae Plantae 1671336

Showing of synonyms

  • Zdero C, Bohlmann F. (1990). Germacranolides from Gutenbergia cordifolia. Phytochemistry,1990,29(8),2706-2708. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O=C(O1)C(=C)C(CC2)C1CCCCC(O3)C23

Level: 0

Mol. Weight: 378.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.15
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
-2.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.38
Plasma Protein Binding
16.03
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
13.39
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.48
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.17
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.25
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-9.78
Rat (Acute)
4.88
Rat (Chronic Oral)
1.54
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
388.01
Hydration Free Energy
-7.07
Log(D) at pH=7.4
1.21
Log(P)
0.85
Log S
-2.94
Log(Vapor Pressure)
-7.48
Melting Point
104.68
pKa Acid
5.53
pKa Basic
2.66
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8045
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8045
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7426
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7426

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