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

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

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8alpha-isobutanoyloxy-3beta,4alpha,10alpha-trihydroxy-1beta,2beta-epoxy-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@]([C@H]([C@H]3O2)O)(C)O
InChI InChI=1S/C19H28O8/c1-7(2)15(21)25-9-6-17(4,23)19-12(11-10(9)8(3)16(22)26-11)18(5,24)13(20)14(19)27-19/h7-14,20,23-24H,6H2,1-5H3/t8-,9-,10+,11-,12-,13-,14+,17+,18-,19-/m0/s1
InChIKey FWGYSXFXRHTSJT-JKEBHUFOSA-N
Formula C19H28O8
HBA 8
HBD 3
MW 384.43
Rotatable Bonds 2
TPSA 125.82
LogP -0.23
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.89
Exact Mass 384.18
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: 162984049
Nmrshiftdb2: 60056749

No compound-protein relationship available.

Structure

SMILES: C123C(O3)CCC1C4C(CC(=O)O4)CCC2

Level: 0

Mol. Weight: 384.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.24
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.780
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.19

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.290
Plasma Protein Binding
35.7
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
9.430
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.210
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.430
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.970
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
-6.780
Rat (Acute)
4.770
Rat (Chronic Oral)
2.300
Fathead Minnow
3.760
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
391.940
Hydration Free Energy
-9.130
Log(D) at pH=7.4
-0.270
Log(P)
0.15
Log S
-2.16
Log(Vapor Pressure)
-8.25
Melting Point
150.73
pKa Acid
5.34
pKa Basic
2.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7785
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7785
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7456
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7456
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7166
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7166

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