5alpha-chloro-4beta,10alpha-dihydroxy-1alpha,2alpha-epoxy-8alpha-valeryloxy-11,13-dehydroguaia-6alpha,12-olide - Compound Card

5alpha-chloro-4beta,10alpha-dihydroxy-1alpha,2alpha-epoxy-8alpha-valeryloxy-11,13-dehydroguaia-6alpha,12-olide

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5alpha-chloro-4beta,10alpha-dihydroxy-1alpha,2alpha-epoxy-8alpha-valeryloxy-11,13-dehydroguaia-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(CC(=O)O[C@H]1C[C@@](C)(O)[C@]23[C@]([C@@H]4[C@@H]1[C@H](C)C(=O)O4)(Cl)[C@@](C[C@@H]3O2)(C)O)C
InChI InChI=1S/C20H29ClO7/c1-9(2)6-13(22)26-11-7-18(5,25)20-12(28-20)8-17(4,24)19(20,21)15-14(11)10(3)16(23)27-15/h9-12,14-15,24-25H,6-8H2,1-5H3/t10-,11-,12-,14+,15-,17-,18+,19+,20+/m0/s1
InChIKey HKSBPBVXBSYDAT-LPOBFPNRSA-N
Formula C20H29ClO7
HBA 7
HBD 2
MW 416.9
Rotatable Bonds 3
TPSA 105.59
LogP 1.55
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 416.16
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: 14021388
Nmrshiftdb2: 60056750

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 416.9 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.09
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.75
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.34
Plasma Protein Binding
32.13
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
10.75
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.53
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.03
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.4
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
-8.78
Rat (Acute)
5.02
Rat (Chronic Oral)
1.72
Fathead Minnow
3.88
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
402.63
Hydration Free Energy
-7.1
Log(D) at pH=7.4
1.08
Log(P)
1.84
Log S
-3.04
Log(Vapor Pressure)
-7.16
Melting Point
139.24
pKa Acid
5.19
pKa Basic
3.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7345
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7345
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7291
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7291
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7139
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7139

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