1alpha,4alpha,10alpha-trihydroxy-2beta,3beta-epoxy-8alpha-methylbutanoyloxy-11,13-dehydroguaia-6alpha,12-olide - Compound Card

1alpha,4alpha,10alpha-trihydroxy-2beta,3beta-epoxy-8alpha-methylbutanoyloxy-11,13-dehydroguaia-6alpha,12-olide

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1alpha,4alpha,10alpha-trihydroxy-2beta,3beta-epoxy-8alpha-methylbutanoyloxy-11,13-dehydroguaia-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CCC(C(=O)O[C@H]1C[C@@](C)(O)[C@]2([C@@H]([C@@H]3[C@@H]1[C@H](C)C(=O)O3)[C@]([C@@H]1[C@H]2O1)(C)O)O)C
InChI InChI=1S/C20H30O8/c1-6-8(2)16(21)26-10-7-18(4,23)20(25)13(19(5,24)14-15(20)28-14)12-11(10)9(3)17(22)27-12/h8-15,23-25H,6-7H2,1-5H3/t8?,9-,10-,11+,12-,13-,14-,15+,18+,19-,20+/m0/s1
InChIKey BNSRRGINQVIFFG-FRRZKKIMSA-N
Formula C20H30O8
HBA 8
HBD 3
MW 398.45
Rotatable Bonds 3
TPSA 125.82
LogP 0.16
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 398.19
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: 162917724
Nmrshiftdb2: 60056759

No compound-protein relationship available.

Structure

SMILES: C12C(O2)CC3C1CCCC4C3OC(=O)C4

Level: 0

Mol. Weight: 398.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.15
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.77
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.33
Plasma Protein Binding
37.96
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
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.21
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
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
0.32
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.91
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
-10.91
Rat (Acute)
4.86
Rat (Chronic Oral)
2.25
Fathead Minnow
3.81
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
400.38
Hydration Free Energy
-8.48
Log(D) at pH=7.4
0.09
Log(P)
0.79
Log S
-2.53
Log(Vapor Pressure)
-8.57
Melting Point
154.72
pKa Acid
5.55
pKa Basic
3.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7347
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7347
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7280
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7280
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7021
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7021

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