5-alpha-hydroxy-2-oxo-8alpha-isovaleryloxy-11,13-dehydroguaia-1(10),3-dien-6alpha,12-olide - Compound Card

5-alpha-hydroxy-2-oxo-8alpha-isovaleryloxy-11,13-dehydroguaia-1(10),3-dien-6alpha,12-olide

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5-alpha-hydroxy-2-oxo-8alpha-isovaleryloxy-11,13-dehydroguaia-1(10),3-dien-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(CC(=O)O[C@H]1CC(=C2[C@]([C@@H]3[C@@H]1[C@H](C)C(=O)O3)(O)C(=CC2=O)C)C)C
InChI InChI=1S/C20H26O6/c1-9(2)6-15(22)25-14-7-10(3)17-13(21)8-11(4)20(17,24)18-16(14)12(5)19(23)26-18/h8-9,12,14,16,18,24H,6-7H2,1-5H3/t12-,14-,16+,18-,20+/m0/s1
InChIKey KXARZMGWVGLTJB-RRTUYPMLSA-N
Formula C20H26O6
HBA 6
HBD 1
MW 362.42
Rotatable Bonds 3
TPSA 89.9
LogP 2.1
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 362.17
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: 14021360

No compound-protein relationship available.

Structure

SMILES: O=C1C=CC(C1=2)C3C(CC(=O)O3)CCC2

Level: 0

Mol. Weight: 362.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.53
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.54

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.39
Plasma Protein Binding
65.13
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
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
8.02
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.02
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.58
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.96
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1.18
Rat (Acute)
3.59
Rat (Chronic Oral)
2.19
Fathead Minnow
3.93
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
375.11
Hydration Free Energy
-6.98
Log(D) at pH=7.4
1.61
Log(P)
2.57
Log S
-3.25
Log(Vapor Pressure)
-6.73
Melting Point
160.31
pKa Acid
7.0
pKa Basic
4.36
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 0.8567
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8567
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7728
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7728
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7639
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7639

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