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

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

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1alpha,4alpha,10alpha-trihydroxy-8alpha-methylbutanoyloxy-11,13-dehydroguaia-2-en-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=C2)(C)O)O)C
InChI InChI=1S/C20H30O7/c1-6-10(2)16(21)26-12-9-19(5,24)20(25)8-7-18(4,23)15(20)14-13(12)11(3)17(22)27-14/h7-8,10-15,23-25H,6,9H2,1-5H3/t10?,11-,12-,13+,14-,15-,18+,19+,20-/m0/s1
InChIKey OPGJIRGRIDHFPI-KYLBNMPHSA-N
Formula C20H30O7
HBA 7
HBD 3
MW 382.45
Rotatable Bonds 3
TPSA 113.29
LogP 0.94
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 382.2
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: 163010567
Nmrshiftdb2: 60056732

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC2C1CCCC(C23)C=CC3

Level: 0

Mol. Weight: 382.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.6
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.77
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.74

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
56.88
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.07
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.47
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.67
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.86
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
-5.5
Rat (Acute)
3.8
Rat (Chronic Oral)
2.14
Fathead Minnow
3.96
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
384.08
Hydration Free Energy
-9.21
Log(D) at pH=7.4
1.08
Log(P)
0.83
Log S
-2.71
Log(Vapor Pressure)
-7.93
Melting Point
162.27
pKa Acid
6.72
pKa Basic
4.84
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7182
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7182
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7038
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7038

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