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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C(C(C)C)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
InChI InChI=1S/C19H26O7/c1-7(2)15(20)23-9-6-17(4,22)19-12(11-10(9)8(3)16(21)24-11)18(5)13(25-18)14(19)26-19/h7-14,22H,6H2,1-5H3/t8-,9-,10+,11-,12-,13-,14+,17+,18+,19-/m0/s1
InChIKey DYYUKEWJHDHASM-RFYDPHEBSA-N
Formula C19H26O7
HBA 7
HBD 1
MW 366.41
Rotatable Bonds 2
TPSA 97.89
LogP 0.81
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.89
Exact Mass 366.17
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: 162816885

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 366.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.15
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.730
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.180
Plasma Protein Binding
25.09
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
13.020
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.340
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.120
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.350
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
-6.790
Rat (Acute)
4.630
Rat (Chronic Oral)
1.600
Fathead Minnow
3.760
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
398.660
Hydration Free Energy
-6.380
Log(D) at pH=7.4
0.670
Log(P)
0.78
Log S
-2.42
Log(Vapor Pressure)
-7.18
Melting Point
127.33
pKa Acid
5.21
pKa Basic
2.13
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7284
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7284

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