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

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

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10alpha-hydroxy-1alpha,2alpha,3alpha,4alpha-diepoxy-8-alpha-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@]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/C20H28O7/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/h8-15,23H,6-7H2,1-5H3/t8?,9-,10-,11+,12-,13-,14+,15-,18+,19-,20+/m0/s1
InChIKey PECBKFURXWMWOB-HLQDBOLLSA-N
Formula C20H28O7
HBA 7
HBD 1
MW 380.44
Rotatable Bonds 3
TPSA 97.89
LogP 1.2
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 380.18
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: 162816881

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 380.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.06
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.73
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.18
Plasma Protein Binding
27.82
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
13.29
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.27
Biodegradation
Safe
Carcinogenesis
Safe
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
6.55
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
-11.01
Rat (Acute)
4.97
Rat (Chronic Oral)
1.57
Fathead Minnow
3.79
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
407.17
Hydration Free Energy
-6.33
Log(D) at pH=7.4
1.09
Log(P)
1.22
Log S
-2.7
Log(Vapor Pressure)
-7.39
Melting Point
135.35
pKa Acid
5.29
pKa Basic
2.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7665
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7665
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7161
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7161
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7046
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7046

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