8alpha-angeloyloxy-1beta,10alpha,4alpha,5beta-bisepoxy-3beta-hydroxygermacr-11(13)-en-12,6alpha-olide - Compound Card

8alpha-angeloyloxy-1beta,10alpha,4alpha,5beta-bisepoxy-3beta-hydroxygermacr-11(13)-en-12,6alpha-olide

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8alpha-angeloyloxy-1beta,10alpha,4alpha,5beta-bisepoxy-3beta-hydroxygermacr-11(13)-en-12,6alpha-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C=C(\C(=O)O[C@H]1C[C@@]2(C)O[C@@H]2[C@H]2O[C@H]2C(=C)[C@@H]([C@@H]2[C@@H]1C(=C)C(=O)O2)O)/C
InChI InChI=1S/C20H24O7/c1-6-8(2)18(22)24-11-7-20(5)17(27-20)16-14(25-16)10(4)13(21)15-12(11)9(3)19(23)26-15/h6,11-17,21H,3-4,7H2,1-2,5H3/b8-6-/t11-,12+,13-,14-,15-,16-,17+,20+/m0/s1
InChIKey RKAXEWSQYMGBAP-DCYZMOCKSA-N
Formula C20H24O7
HBA 7
HBD 1
MW 376.41
Rotatable Bonds 2
TPSA 97.89
LogP 1.21
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 376.15
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]
Pubchem: 101316721
Nmrshiftdb2: 70034216

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(CC(=C)C2O3)C1CCC(O4)C4C23

Level: 0

Mol. Weight: 376.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.14
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.64
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.25
Plasma Protein Binding
24.84
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.45
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.15
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.22
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.4
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
-12.08
Rat (Acute)
5.35
Rat (Chronic Oral)
1.78
Fathead Minnow
3.96
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
394.45
Hydration Free Energy
-6.36
Log(D) at pH=7.4
0.91
Log(P)
1.09
Log S
-2.73
Log(Vapor Pressure)
-7.71
Melting Point
115.69
pKa Acid
5.19
pKa Basic
1.17
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 0.9303
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9303
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7581
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7581
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7504
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7504
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7345
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7345
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7294
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7294
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7139
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7139
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7122
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7122
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7095
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7095

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