8alpha-angeloyloxy-1beta,10alpha-epoxy-2alpha,15-dihydroxygermacra-4Z,11(13)-dien-12,6alpha-olide - Compound Card

8alpha-angeloyloxy-1beta,10alpha-epoxy-2alpha,15-dihydroxygermacra-4Z,11(13)-dien-12,6alpha-olide

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8alpha-angeloyloxy-1beta,10alpha-epoxy-2alpha,15-dihydroxygermacra-4Z,11(13)-dien-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](O)C/C(=C/[C@@H]2[C@@H]1C(=C)C(=O)O2)/CO)/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/h5,7,13-17,21-22H,3,6,8-9H2,1-2,4H3/b10-5-,12-7-/t13-,14+,15-,16-,17+,20+/m0/s1
InChIKey JUXDHJCYBXOISP-MGRXOGJYSA-N
Formula C20H26O7
HBA 7
HBD 2
MW 378.42
Rotatable Bonds 3
TPSA 105.59
LogP 1.19
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.6
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]
Pubchem: 14707385

No compound-protein relationship available.

Structure

SMILES: O=C(O1)C(=C)C(CC2)C1C=CCCC(O3)C23

Level: 0

Mol. Weight: 378.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.28
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.67
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.39
Plasma Protein Binding
24.48
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
13.15
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.22
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.22
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.78
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
-9.22
Rat (Acute)
4.45
Rat (Chronic Oral)
2.3
Fathead Minnow
3.94
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
403.69
Hydration Free Energy
-7.79
Log(D) at pH=7.4
0.63
Log(P)
0.82
Log S
-2.62
Log(Vapor Pressure)
-7.64
Melting Point
120.29
pKa Acid
5.99
pKa Basic
2.68
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7587
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7587
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7341
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7341
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7233
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7233
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7012
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7012

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