8alpha-angeloyloxy-10alpha-hydroxy-1alpha,2alpha,3alpha,4alpha-diepoxy-11,13-dehydroguaia-6alpha,12-olide - Compound Card

8alpha-angeloyloxy-10alpha-hydroxy-1alpha,2alpha,3alpha,4alpha-diepoxy-11,13-dehydroguaia-6alpha,12-olide

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8alpha-angeloyloxy-10alpha-hydroxy-1alpha,2alpha,3alpha,4alpha-diepoxy-11,13-dehydroguaia-6alpha,12-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@@](C)(O)[C@]23[C@@H]([C@@H]4[C@@H]1[C@H](C)C(=O)O4)[C@]1([C@@H]([C@@H]3O2)O1)C)/C
InChI InChI=1S/C20H26O7/c1-6-8(2)16(21)24-10-7-18(4,23)20-13(12-11(10)9(3)17(22)25-12)19(5)14(26-19)15(20)27-20/h6,9-15,23H,7H2,1-5H3/b8-6-/t9-,10-,11+,12-,13-,14+,15-,18+,19-,20+/m0/s1
InChIKey FWWNLOWYXNKFGQ-WVKRDBPSSA-N
Formula C20H26O7
HBA 7
HBD 1
MW 378.42
Rotatable Bonds 2
TPSA 97.89
LogP 1.12
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 378.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Otanthus maritimus Asteraceae Plantae 1155244

Showing of synonyms

  • Jakupovic J, Boeker R, et al. (1988). Highly oxygenated guaianolides from Otanthus maritimus. Phytochemistry,1988,27(4),1135-1140. [View]
Pubchem: 14021365

No compound-protein relationship available.

Structure

SMILES: C123C(O3)C4C(O4)C1C5C(CC(=O)O5)CCC2

Level: 0

Mol. Weight: 378.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.07
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.71
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.23
Plasma Protein Binding
27.26
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
12.5
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.16
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.27
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.59
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
-14.04
Rat (Acute)
5.02
Rat (Chronic Oral)
1.54
Fathead Minnow
3.9
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
404.22
Hydration Free Energy
-6.19
Log(D) at pH=7.4
1.1
Log(P)
1.18
Log S
-2.74
Log(Vapor Pressure)
-7.38
Melting Point
148.43
pKa Acid
5.34
pKa Basic
1.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7621
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7621
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7562
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7562
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7257
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7257
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7136
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7136

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