4beta,5alpha,10alpha-trihydroxy-1beta,2beta-epoxy-8alpha-desacyloxy-11,13-dehydroguaia-6alpha,12-olide - Compound Card

4beta,5alpha,10alpha-trihydroxy-1beta,2beta-epoxy-8alpha-desacyloxy-11,13-dehydroguaia-6alpha,12-olide

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4beta,5alpha,10alpha-trihydroxy-1beta,2beta-epoxy-8alpha-desacyloxy-11,13-dehydroguaia-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles 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)C)(C)O
InChI InChI=1S/C16H24O6/c1-6-9-8(17)5-14(3,19)16-11(10(9)21-13(6)18)15(4,20)7(2)12(16)22-16/h6-12,17,19-20H,5H2,1-4H3/t6-,7-,8-,9+,10-,11-,12+,14+,15+,16-/m0/s1
InChIKey KSTMSIZFPTTZJM-MUWXPUKWSA-N
Formula C16H24O6
HBA 6
HBD 3
MW 312.36
Rotatable Bonds 0
TPSA 99.52
LogP -0.17
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.94
Exact Mass 312.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pentzia albida Asteraceae Plantae 1721051

Showing of synonyms

  • Jakupovic J, Boeker R, et al. (1988). Highly oxygenated guaianolides from Otanthus maritimus. Phytochemistry,1988,27(4),1135-1140. [View]
Pubchem: 163064527

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 312.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.31
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
-2.03

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.14
Plasma Protein Binding
31.35
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
10.73
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.46
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.11
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.33
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
-2.09
Rat (Acute)
4.31
Rat (Chronic Oral)
1.95
Fathead Minnow
3.37
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
388.8
Hydration Free Energy
-9.87
Log(D) at pH=7.4
-0.6
Log(P)
-0.16
Log S
-1.58
Log(Vapor Pressure)
-7.47
Melting Point
156.62
pKa Acid
5.34
pKa Basic
4.37
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7512
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7512
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7284
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7284

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